Compounds > 6-(3'-(1-adamantyl)-4'-hydroxyphenyl)-5-chloronaphthalenecarboxylic acid
Page last updated: 2024-11-12

6-(3'-(1-adamantyl)-4'-hydroxyphenyl)-5-chloronaphthalenecarboxylic acid

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Cross-References

ID SourceID
PubMed CID10342802
CHEMBL ID118143
MeSH IDM0469911

Synonyms (3)

Synonym
5-cl-ahpn
CHEMBL118143
6-[3-(1-adamantyl)-4-hydroxyphenyl]-5-chloronaphthalene-2-carboxylic acid
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (22)

Assay IDTitleYearJournalArticle
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.
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
AID78409Inhibition of H460 cell proliferation after 144 hr 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.
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
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
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
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.
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
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
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
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.
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
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
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
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
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.
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.
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
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
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.
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.
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
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (60.00)29.6817
2010's2 (40.00)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: 12.63

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 Index12.63 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.42 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.63)

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%
Other5 (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
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.		3.1450adamantanes;
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.		2.7430retinoic 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
adarotene
adarotene: structure in first source		3.1450
4-(3-(1-adamantyl)-4-hydroxyphenyl)-3-chlorocinnamic acid
[no description available]		3.1450
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