Compounds > 4-(3-(1-adamantyl)-4-hydroxyphenyl)-3-chlorocinnamic acid
Page last updated: 2024-12-11

4-(3-(1-adamantyl)-4-hydroxyphenyl)-3-chlorocinnamic acid

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Cross-References

ID SourceID
PubMed CID9866186
CHEMBL ID176252
SCHEMBL ID1914213
MeSH IDM0458208

Synonyms (9)

Synonym
bdbm25122
(2e)-3-{4-[3-(adamantan-1-yl)-4-hydroxyphenyl]-3-chlorophenyl}prop-2-enoic acid
(e)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid
3-cl-ahpc
CHEMBL176252
SCHEMBL1914213
(e)-3-[4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorophenyl]prop-2-enoic acid
4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid
PD003704
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Tyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)IC50 (µMol)2.10000.31804.00429.6000AID1798517; AID364175
Nuclear receptor subfamily 0 group B member 2Homo sapiens (human)IC50 (µMol)2.50002.50002.50002.5000AID364173
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (70)

Processvia Protein(s)Taxonomy
DNA damage checkpoint signalingTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
protein dephosphorylationTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
triglyceride metabolic processTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
epidermal growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
integrin-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
axonogenesisTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
brain developmentTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
heart developmentTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
fibroblast growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
hormone-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
cytokine-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
cerebellar cortex formationTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
platelet formationTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
T cell costimulationTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
negative regulation of chondrocyte differentiationTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
negative regulation of type I interferon productionTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
microvillus organizationTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
positive regulation of interferon-beta productionTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
positive regulation of interleukin-6 productionTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
positive regulation of tumor necrosis factor productionTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
regulation of cell adhesion mediated by integrinTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
negative regulation of cell adhesion mediated by integrinTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
multicellular organism growthTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
organ growthTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
peptidyl-tyrosine dephosphorylationTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
megakaryocyte developmentTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
atrioventricular canal developmentTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
ERBB signaling pathwayTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
hormone metabolic processTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
glucose homeostasisTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
regulation of protein-containing complex assemblyTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
positive regulation of ossificationTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
positive regulation of mitotic cell cycleTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
positive regulation of glucose importTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
positive regulation of insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
negative regulation of insulin secretionTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
regulation of protein export from nucleusTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
positive regulation of hormone secretionTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
platelet-derived growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
neurotrophin TRK receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
ephrin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
multicellular organismal reproductive processTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
genitalia developmentTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
inner ear developmentTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
homeostasis of number of cells within a tissueTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylationTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
negative regulation of cortisol secretionTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
Bergmann glial cell differentiationTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
negative regulation of growth hormone secretionTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
face morphogenesisTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
regulation of type I interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
intestinal epithelial cell migrationTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
cellular response to epidermal growth factor stimulusTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
positive regulation of DNA-templated transcriptionNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
Notch signaling pathwayNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
circadian rhythmNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
cholesterol metabolic processNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
response to glucoseNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
positive regulation of gene expressionNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
negative regulation of gene expressionNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
response to organic cyclic compoundNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
bile acid and bile salt transportNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
animal organ regenerationNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
positive regulation of insulin secretionNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
circadian regulation of gene expressionNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
negative regulation of DNA-binding transcription factor activityNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
response to ethanolNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
negative regulation of DNA-templated transcriptionNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
negative regulation of transcription by RNA polymerase IINuclear receptor subfamily 0 group B member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
phosphotyrosine residue bindingTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
phosphoprotein phosphatase activityTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
insulin receptor bindingTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
protein bindingTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
protein kinase bindingTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
signaling receptor complex adaptor activityTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
cadherin bindingTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
cell adhesion molecule bindingTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
peptide hormone receptor bindingTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
molecular adaptor activityTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
protein tyrosine kinase bindingTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
receptor tyrosine kinase bindingTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
transcription corepressor activityNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
protein bindingNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
protein domain specific bindingNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
protein homodimerization activityNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
peroxisome proliferator activated receptor bindingNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
protein-containing complex bindingNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
nuclear retinoid X receptor bindingNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
nuclear thyroid hormone receptor bindingNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
transcription regulator inhibitor activityNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
transcription factor bindingNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
cytoplasmTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
nucleusTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
nucleoplasmTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
cytosolTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
protein-containing complexTyrosine-protein phosphatase non-receptor type 11Homo sapiens (human)
nucleusNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
nucleoplasmNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
cytoplasmNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
intracellular membrane-bounded organelleNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
chromatinNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
cytoplasmNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
nucleusNuclear receptor subfamily 0 group B member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (121)

Assay IDTitleYearJournalArticle
AID288598Induction of apoptosis in HMVE cells at 0.5 uM after 20 hrs relative to adriamycin2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID646005Antiproliferative activity against human MOLT4 cells assessed as cell viability after 72 hrs by luciferase assay2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID288589Growth inhibition of retinoid-resistant DU145 cells at 1 uM relative to control2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID82680Induction of apoptosis in HL60R leukemia cells after 24 hr r treatment at 1E-6M2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID248352Concentration of compound required for inhibition of (NB4) human promyelocytic leukemia cell growth by 50%2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.
AID645997Induction of apoptosis in human ATRA-resistant HL60R cells at 0.1 uM after 24 hrs2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID646007Antiproliferative activity against human OCI-AML2 cells assessed as cell viability at 5 uM after 72 hrs by luciferase assay2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID1069756Inhibition of recombinant IKKbeta (unknown origin) using ulight-IkappaomegaBalpha as substrate at 20 uM after 2 hrs by LANCE ultra TR-FRET assay relative to control2014Bioorganic & medicinal chemistry, Feb-15, Volume: 22, Issue:4
Inhibition of IκB kinase-β and IκB kinase-α by heterocyclic adamantyl arotinoids.
AID610856Induction of apoptosis in retinoid-resistant p53 null human HL60R cells assessed as DNA fragmentation at 1 uM after 24 hrs by acridine orange staining method2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID288585Growth inhibition of retinoid-resistant MDA-MB-231 cells at 1 uM relative to control2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID610852Growth inhibition in human KG1 cells expressing p53 gene at 5 uM after 48 hrs by MTT assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID288590Inhibition of cell proliferation in retinoid-resistant KG1 cells after 48 hrs2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID365056Antiproliferative activity against human MDA-MB-231 cells at 2.5 uM after 72 hrs by MTT assay2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID610176Toxicity in ICR-SCIDS mouse assessed as decrease in body weight at 20 mg/kg, iv qd administered at a 25% increment in dose each day for 7 days measured on day 7 relative to body weight on day 12011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID420845Induction of apoptosis in human Jurkat T cells assessed as induction of DEVDase activity at 1 uM after 4 hrs by fluorescence assay2009European journal of medicinal chemistry, Jun, Volume: 44, Issue:6
Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.
AID198193Displacement of [3H]9-cis-RA from Retinoic acid receptor alpha LBD2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID288596Growth inhibition of primary HMVE cells after 72 hrs2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID646009Antiproliferative activity against mouse MMTV-Wnt-1 cells assessed as cell viability after 72 hrs by DAPI staining method2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID610167Induction of apoptosis in human PC3 cells assessed as decrease in ATP level at 10 uM after 72 hrs by luminescence assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID365051Antiproliferative activity against human DU145 cells at 2.5 uM after 72 hrs by MTT assay2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID288586Growth inhibition of retinoid-resistant H292 cells after 72 hrs2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID610165Induction of apoptosis in human HT-29 cells assessed as decrease in ATP level at 10 uM after 72 hrs by luminescence assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID288582Induction of apoptosis in retinoid-resistant KG1 cells at 1 uM after 48 hrs2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID288584Growth inhibition of retinoid-resistant MDA-MB-231 cells after 72 hrs2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID610867Induction of apoptosis in retinoid-resistant human MDA-MB-231 cells expressing p53 and ERbeta gene assessed as DNA fragmentation at 1 uM after 24 hrs by acridine orange staining method2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID610868Induction of apoptosis in retinoid-resistant human MDA-MB-231 cells expressing p53 and ERbeta gene assessed as DNA fragmentation at 1 uM after 48 hrs by acridine orange staining method2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID645998Induction of apoptosis in human ATRA-resistant HL60R cells at 1 uM after 24 hrs2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID288591Inhibition of cell proliferation in retinoid-resistant KG1 cells at 1 uM after 48 hrs relative to control2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID610184Induction of apoptosis in human PC3 cells assessed as decrease in ATP level at 5 uM after 72 hrs by luminescence assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID610249Induction of apoptosis in retinoid-resistant human MDA-MB-231 cells expressing p53 and Erbeta gene assessed as DNA fragmentation at 0.1 to 1 uM after 48 hrs by acridine orange staining method2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID610858Aqueous solubility of the compound in water at pH 5 by UV spectrophotometric analysis2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID610168Induction of apoptosis in human A549 cells assessed as decrease in ATP level after 72 hrs by luminescence assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID365035Induction of apoptosis in human MDA-MB-231 cells at 1.0 uM after 96 hrs by acridine orange staining2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID610171Induction of apoptosis in human PC3 cells assessed as decrease in ATP level at 5 to 10 uM after 72 hrs by luminescence assay relative to control2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID646008Antiproliferative activity against human MOLT4 cells assessed as cell viability at 5 uM after 72 hrs by luciferase assay2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID610175Toxicity in ICR-SCIDS mouse assessed as increase in body weight at 20 mg/kg, iv qd administered at a 25% increment in dose each day for 7 days measured on day 42011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID288587Growth inhibition of retinoid-resistant H292 cells at 1 uM relative to control2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID610166Induction of apoptosis in human A549 cells assessed as decrease in ATP level at 10 uM after 72 hrs by luminescence assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID288601Effect on tubule formation of HMVE cells in Matrigel assessed as tube length after 18 hrs2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID646000Induction of apoptosis in human KG1 cells at 5 uM after 48 hrs using acridine orange staining2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID420839Antiproliferative activity against human SKOV3 cells at 4 uM after 48 hrs by MTT assay2009European journal of medicinal chemistry, Jun, Volume: 44, Issue:6
Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.
AID420940Displacement of [3H]9cRA from RARgamma2009European journal of medicinal chemistry, Jun, Volume: 44, Issue:6
Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.
AID364173Displacement of [5,5'-3H2]AHPN from human recombinant GST-SHP by liquid scintillation counting relative to 3-Cl-AHPC2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID365042Induction of apoptosis in human KG1 cells at 5.0 uM after 48 hrs by acridine orange staining2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID610164Induction of apoptosis in mouse MMTV-Wnt-1 cells assessed as cell viability after 72 hrs by DAPI staining based cell counting2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID248756Concentration of compound required for inhibition of (IGROV-1/Pt1) human cisplatin resistant ovarian carcinoma cell growth by 50%2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.
AID610851Growth inhibition in human KG1 cells expressing p53 gene at 1 uM after 48 hrs by MTT assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID645995Growth inhibition of human MDA-MB-231 cells at 1 uM after 96 hrs2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID610177Toxicity in ICR-SCIDS mouse assessed as decrease in body weight at 20 mg/kg, iv qd administered at a 25% increment in dose each day for 7 days measured on day 8 relative to control2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID365034Induction of apoptosis in human HL60R cells at 1.0 uM after 24 hrs by acridine orange staining2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID288599Inhibition of HMVE cell migration through Matrigel after 5 hrs2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID1069753Cytotoxicity against human Jurkat T cells assessed as cell viability at 4 uM after 24 hrs by CellTiter-Glo assay relative to control2014Bioorganic & medicinal chemistry, Feb-15, Volume: 22, Issue:4
Inhibition of IκB kinase-β and IκB kinase-α by heterocyclic adamantyl arotinoids.
AID610185Induction of apoptosis in human HT-29 cells assessed as decrease in ATP level at 5 uM after 72 hrs by luminescence assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID365041Induction of apoptosis in human KG1 cells at 1.0 uM after 48 hrs by acridine orange staining2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID251334Percent level of apoptosis induced by 72 hr of exposure with IC80 in (IGROV-1) human ovarian carcinoma cells2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.
AID420840Antiproliferative activity against human A549 cells at 4 uM after 72 hrs by MTT assay2009European journal of medicinal chemistry, Jun, Volume: 44, Issue:6
Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.
AID288576Antiproliferative activity against HMVE cells2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID610170Induction of apoptosis in human A549 cells assessed as decrease in ATP level at 5 to 10 uM after 72 hrs by luminescence assay relative to control2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID101801Induction of apoptosis in MDA-MB-231 breast cancer cells after 96 hr at 0.5E-6M2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID288575Induction of apoptosis in MDA-MB-231 cells at 1 uM after 96 hrs2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID645994Growth inhibition of human KG1 cells at 5 uM after 48 hrs by hemocytometer2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID420838Antiproliferative activity against human PC3 cells at 4 uM after 48 hrs by MTT assay2009European journal of medicinal chemistry, Jun, Volume: 44, Issue:6
Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.
AID1069757Inhibition of recombinant IKKalpha (unknown origin) using ulight-IkappaomegaBalpha as substrate at 20 uM after 2 hrs by LANCE ultra TR-FRET assay relative to control2014Bioorganic & medicinal chemistry, Feb-15, Volume: 22, Issue:4
Inhibition of IκB kinase-β and IκB kinase-α by heterocyclic adamantyl arotinoids.
AID288602Displacement of [5,5'-3H2]AHPN from recombinant human GST-SHP partner nuclear orphan receptor at 50 uM2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID610855Induction of apoptosis in retinoid-resistant p53 null human HL60R cells assessed as DNA fragmentation at 0.1 uM after 24 hrs by acridine orange staining method2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID610169Induction of apoptosis in human PC3 cells assessed as decrease in ATP level after 72 hrs by luminescence assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID610248Growth inhibition of retinoid-resistant human MDA-MB-231 cells expressing p53 and Erbeta gene at 0.1 to 1 uM after 48 hrs by MTT assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID199651Displacement of [3H]9-cis-RA from Retinoic acid receptor RXR-alpha LBD2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID610183Induction of apoptosis in human A549 cells assessed as decrease in ATP level at 5 uM after 72 hrs by luminescence assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID365040Growth inhibition of HMVE cells at 0.5 uM after 72 hrs by alamar blue method2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID610865Growth inhibition of retinoid-resistant human MDA-MB-231 cells expressing p53 and ERbeta gene at 1 uM after 24 hrs by MTT assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID82679Induction of apoptosis in HL60R leukemia cells after 24 hr r treatment at 0.1E-6M2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID610853Induction of apoptosis in human KG1 cells expressing p53 gene assessed as DNA fragmentation at 1 uM after 48 hrs by acridine orange staining method2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID288603Induction of apoptosis in retinoid-resistant KG1 cells at 5 uM after 48 hrs2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID420842Antiproliferative activity against human BxPC3 cells at 4 uM after 48 hrs by MTT assay2009European journal of medicinal chemistry, Jun, Volume: 44, Issue:6
Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.
AID420843Antiproliferative activity against human T47D cells at 4 uM after 48 hrs by MTT assay2009European journal of medicinal chemistry, Jun, Volume: 44, Issue:6
Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.
AID364174Displacement of [5,5'-3H2]AHPN from human recombinant GST-SHP at 50 uM by liquid scintillation counting relative to 3-Cl-AHPC2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID365061Antiproliferative activity against human H292 cells at 2.5 uM after 72 hrs by MTT assay2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID288583Growth inhibition of retinoid-resistant KG1 cells at 5 uM after 48 hrs2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID646003Antiproliferative activity against human K562 cells assessed as cell viability after 72 hrs by luciferase assay2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID646010Binding affinity to GST-tagged human recombinant SHP at 100 uM by NMR spectroscopy2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID365049Antiproliferative activity against human KG1 AML cells at 5 uM after 48 hrs by MTT assay2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID105061Inhibition of MDA-MB-468 cell proliferation at 0.5E-6M; Inhibitory activity2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID646006Antiproliferative activity against human K562 cells assessed as cell viability at 5 uM after 72 hrs by luciferase assay2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID365048Antiproliferative activity against human H292 cells after 72 hrs by MTT assay2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID288600Inhibition of HMVE cell tubule formation in Matrigel after 18 hrs2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID646002Induction of apoptosis in human MDA-MB-231 cells at 2 uM after 96 hrs2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID420938Displacement of [3H]9cRA from RARalpha2009European journal of medicinal chemistry, Jun, Volume: 44, Issue:6
Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.
AID420841Antiproliferative activity against human MIAPaCa2 cells at 4 uM after 48 hrs by MTT assay2009European journal of medicinal chemistry, Jun, Volume: 44, Issue:6
Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.
AID420939Displacement of [3H]9cRA from RARbeta2009European journal of medicinal chemistry, Jun, Volume: 44, Issue:6
Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.
AID645993Growth inhibition of human KG1 cells at 1 uM after 48 hrs by hemocytometer2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID288588Growth inhibition of retinoid-resistant DU145 cells after 72 hrs2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID610172Induction of apoptosis in human HT-29 cells assessed as decrease in ATP level at 10 uM after 72 hrs by luminescence assay relative to control2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID1069751Induction of apoptosis in human Jurkat cells assessed as activation of DEVDase at 5 uM after 4 hrs by fluorometric assay relative to control2014Bioorganic & medicinal chemistry, Feb-15, Volume: 22, Issue:4
Inhibition of IκB kinase-β and IκB kinase-α by heterocyclic adamantyl arotinoids.
AID101803Induction of apoptosis in MDA-MB-231 breast cancer cells after 96 hr at 1E-6M2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID420844Antiproliferative activity against human MDA-MB-468 cells at 4 uM after 48 hrs by MTT assay2009European journal of medicinal chemistry, Jun, Volume: 44, Issue:6
Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.
AID365039Growth inhibition of HMVE cells after 72 hrs by alamar blue method2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID78410Inhibition of H460 cell proliferation after 144 hr treatment at 0.1E-6M; - denotes not determined2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID645999Induction of apoptosis in human KG1 cells at 1 uM after 48 hrs using acridine orange staining2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID365046Antiproliferative activity against human DU145 cells after 72 hrs by MTT assay2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID364175Inhibition of SHP2 overexpressed in human KG1 cells2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID646001Induction of apoptosis in human MDA-MB-231 cells at 1 uM after 96 hrs2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID365033Induction of apoptosis in human HL60R cells at 0.1 uM after 24 hrs by acridine orange staining2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID610854Induction of apoptosis in human KG1 cells assessed as DNA fragmentation at 5 uM after 48 hrs by acridine orange staining method2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID365047Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by MTT assay2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID420941Displacement of [3H]9cRA from RXRalpha2009European journal of medicinal chemistry, Jun, Volume: 44, Issue:6
Highly twisted adamantyl arotinoids: synthesis, antiproliferative effects and RXR transactivation profiles.
AID645996Growth inhibition of human MDA-MB-231 cells at 2 uM after 96 hrs2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID646004Antiproliferative activity against human OCI-AML2 cells assessed as cell viability after 72 hrs by luciferase assay2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of
AID610857Aqueous solubility of the compound in PBS at pH 7.2 by UV spectrophotometric analysis2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID248330Concentration of compound required for inhibition of (IGROV-1) human ovarian carcinoma cell growth by 50%2005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.
AID288577Inhibition of HMVE cell proliferation at 0.5 uM relative to control2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID610866Growth inhibition of retinoid-resistant human MDA-MB-231 cells expressing p53 and ERbeta gene at 1 uM after 48 hrs by MTT assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID1069755Inhibition of recombinant IKKepsilon (unknown origin) using ulight-rpS6 as substrate at 20 uM after 1 hr by LANCE ultra TR-FRET assay relative to control2014Bioorganic & medicinal chemistry, Feb-15, Volume: 22, Issue:4
Inhibition of IκB kinase-β and IκB kinase-α by heterocyclic adamantyl arotinoids.
AID365045Antiproliferative activity against human KG1 AML cells after 48 hrs by MTT assay2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID288597Induction of apoptosis in HMVE cells assessed as increase in oligonucleosome levels after 20 hrs by ELISA2007Journal of medicinal chemistry, May-31, Volume: 50, Issue:11
An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and
AID610174Toxicity in ICR-SCIDS mouse assessed as increase in body weight at 20 mg/kg, iv qd administered at a 25% increment in dose each day for 7 days measured on day 12011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID78411Inhibition of H460 cell proliferation after 144 hr treatment at 1E-6M2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.
AID610173Induction of apoptosis in human HT-29 cells assessed as decrease in ATP level after 72 hrs by luminescence assay2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.
AID365036Induction of apoptosis in human MDA-MB-231 cells at 2.0 uM after 96 hrs by acridine orange staining2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID365043Induction of apoptosis in human KG1 cells after 48 hrs by acridine orange staining2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
AID1798517Inhibition of PTP Activity from Article 10.1021/jm800456k: \\Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of 2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (62.50)29.6817
2010's3 (37.50)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.20

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.20 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.40 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adapalene
Adapalene: A naphthalene derivative that has specificity for RETINOIC ACID RECEPTORS. It is used as a DERMATOLOGIC AGENT for the treatment of ACNE.. adapalene : A naphthoic acid that is CD437 in which the phenolic hydroxy group has been converted to its methyl ether.		2.0410adamantanes;
monocarboxylic acid;
naphthoic acid		dermatologic drug;
EC 2.7.11.22 (cyclin-dependent kinase) inhibitor;
non-steroidal anti-inflammatory drug
bexarotene
[no description available]		2.0510benzoic acids;
naphthalenes;
retinoid		antineoplastic agent
cd 437
CD 437: selective for retinoic acid receptors gamma. CD437 : A naphthoic acid that is 6-phenylnaphthylene-2-carboxyic acid in which the phenyl substituent has been substituted at positions 3 and 4 by adamant-1-yl and hydroxy groups, respectively. It acts as a selective agonist of retinoic acid receptor (RAR)gamma and induces cell cycle arrest and apoptosis in various cancer cells.		3.2960adamantanes;
monocarboxylic acid;
naphthoic acid;
phenols		apoptosis inducer;
retinoic acid receptor gamma agonist
6-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acid
6-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acid: reverses keratinization process in hamster tracheal organ culture; inhibits induction of ornithine decarboxylase; structure & RN given in first source; RN not in Chemline 12/5/83		2.0310
tretinoin
Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.		2.9740retinoic acid;
vitamin A		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
AP-1 antagonist;
human metabolite;
keratolytic drug;
retinoic acid receptor agonist;
retinoid X receptor agonist;
signalling molecule
alitretinoin
Alitretinoin: A retinoid that is used for the treatment of chronic hand ECZEMA unresponsive to topical CORTICOSTEROIDS. It is also used to treat cutaneous lesions associated with AIDS-related KAPOSI SARCOMA.		2.0510retinoic acidantineoplastic agent;
keratolytic drug;
metabolite;
retinoid X receptor agonist
adarotene
adarotene: structure in first source		3.2960
bms 204493
BMS-493 : A member of the class of dihydronaphthalenes that is 1,2-dihydronaphthalene which is substituted at positions 1, 1, 4, and 6 by methyl, methyl, phenylethynyl, and 2-(p-carboxyphenyl)vinyl groups, respectively (the E isomer).		2.4720acetylenic compound;
benzoic acids;
dihydronaphthalenes;
stilbenoid		retinoic acid receptor antagonist
6-(3'-(1-adamantyl)-4'-hydroxyphenyl)-5-chloronaphthalenecarboxylic acid
[no description available]		3.1450
uvi 3003
UVI 3003: structure in first source		2.4720
cd 3254
CD 3254: structure in first source		2.110
ConditionIndicatedRelationship StrengthStudiesTrials
Benign Neoplasms
[description not available]		02.0410
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.0410
Acute Myelogenous Leukemia
[description not available]		02.0610
Leukemia, Myeloid, Acute
Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.		02.0610
Leucocythaemia
[description not available]		02.0710
Leukemia
A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)		02.0710