Page last updated: 2024-11-09

2-(2,6-diisopropylphenyl)-5-amino-1h-isoindole-1,3-dione

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2-(2,6-diisopropylphenyl)-5-amino-1H-isoindole-1,3-dione: an antineoplastic agent; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1235479
CHEMBL ID90558
SCHEMBL ID2818285
MeSH IDM0582380

Synonyms (18)

Synonym
CHEMBL90558 ,
bdbm50075333
5-amino-2-(2,6-diisopropylphenyl)isoindoline-1,3-dione
5-amino-2-(2,6-diisopropyl-phenyl)-isoindole-1,3-dione
5-amino-2-[2,6-di(propan-2-yl)phenyl]isoindole-1,3-dione
100823-03-8
1h-isoindole-1,3(2h)-dione, 5-amino-2-[2,6-bis(1-methylethyl)phenyl]-
SCHEMBL2818285
tc11
DTXSID30361232
clt-003
BS-47334
2-(2,6-diisopropylphenyl)-5-amino-1h-isoindole-1,3-dione
1h-isoindole-1,3(2h)-dione, 5-amino-2-[2,6-bis(1-methylethyl)phenyl]-tc11
HY-129478
CS-0105753
F77208
AKOS040759656

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" However, TC11 showed low water solubility and poor pharmacokinetic properties."( A novel phenylphthalimide derivative, pegylated TC11, improves pharmacokinetic properties and induces apoptosis of high-risk myeloma cells via G2/M cell-cycle arrest.
Aida, S; Hattori, Y; Hozumi, M; Ichikawa, D; Iida, K; Matsushita, M; Sugai, T; Tabata, N; Yamada, T; Yanagawa, H; Yonemura, Y, 2017
)
0.46
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aminopeptidase NHomo sapiens (human)IC50 (µMol)16.80000.40002.11003.9000AID38364
Aminopeptidase NSus scrofa (pig)IC50 (µMol)16.80000.00053.53548.9000AID38364
Dipeptidyl peptidase 4Homo sapiens (human)IC50 (µMol)251.20000.00010.444410.0000AID56226
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (23)

Processvia Protein(s)Taxonomy
angiogenesisAminopeptidase NHomo sapiens (human)
cell differentiationAminopeptidase NHomo sapiens (human)
symbiont entry into host cellAminopeptidase NHomo sapiens (human)
proteolysisAminopeptidase NHomo sapiens (human)
peptide catabolic processAminopeptidase NHomo sapiens (human)
behavioral fear responseDipeptidyl peptidase 4Homo sapiens (human)
response to hypoxiaDipeptidyl peptidase 4Homo sapiens (human)
proteolysisDipeptidyl peptidase 4Homo sapiens (human)
cell adhesionDipeptidyl peptidase 4Homo sapiens (human)
positive regulation of cell population proliferationDipeptidyl peptidase 4Homo sapiens (human)
negative regulation of extracellular matrix disassemblyDipeptidyl peptidase 4Homo sapiens (human)
peptide hormone processingDipeptidyl peptidase 4Homo sapiens (human)
receptor-mediated endocytosis of virus by host cellDipeptidyl peptidase 4Homo sapiens (human)
T cell costimulationDipeptidyl peptidase 4Homo sapiens (human)
regulation of cell-cell adhesion mediated by integrinDipeptidyl peptidase 4Homo sapiens (human)
locomotory exploration behaviorDipeptidyl peptidase 4Homo sapiens (human)
psychomotor behaviorDipeptidyl peptidase 4Homo sapiens (human)
T cell activationDipeptidyl peptidase 4Homo sapiens (human)
endothelial cell migrationDipeptidyl peptidase 4Homo sapiens (human)
symbiont entry into host cellDipeptidyl peptidase 4Homo sapiens (human)
receptor-mediated virion attachment to host cellDipeptidyl peptidase 4Homo sapiens (human)
negative chemotaxisDipeptidyl peptidase 4Homo sapiens (human)
membrane fusionDipeptidyl peptidase 4Homo sapiens (human)
negative regulation of neutrophil chemotaxisDipeptidyl peptidase 4Homo sapiens (human)
glucagon processingDipeptidyl peptidase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
virus receptor activityAminopeptidase NHomo sapiens (human)
aminopeptidase activityAminopeptidase NHomo sapiens (human)
metallopeptidase activityAminopeptidase NHomo sapiens (human)
signaling receptor activityAminopeptidase NHomo sapiens (human)
metalloaminopeptidase activityAminopeptidase NHomo sapiens (human)
zinc ion bindingAminopeptidase NHomo sapiens (human)
peptide bindingAminopeptidase NHomo sapiens (human)
virus receptor activityDipeptidyl peptidase 4Homo sapiens (human)
protease bindingDipeptidyl peptidase 4Homo sapiens (human)
aminopeptidase activityDipeptidyl peptidase 4Homo sapiens (human)
serine-type endopeptidase activityDipeptidyl peptidase 4Homo sapiens (human)
signaling receptor bindingDipeptidyl peptidase 4Homo sapiens (human)
protein bindingDipeptidyl peptidase 4Homo sapiens (human)
serine-type peptidase activityDipeptidyl peptidase 4Homo sapiens (human)
dipeptidyl-peptidase activityDipeptidyl peptidase 4Homo sapiens (human)
identical protein bindingDipeptidyl peptidase 4Homo sapiens (human)
protein homodimerization activityDipeptidyl peptidase 4Homo sapiens (human)
chemorepellent activityDipeptidyl peptidase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (18)

Processvia Protein(s)Taxonomy
extracellular spaceAminopeptidase NHomo sapiens (human)
lysosomal membraneAminopeptidase NHomo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartmentAminopeptidase NHomo sapiens (human)
plasma membraneAminopeptidase NHomo sapiens (human)
external side of plasma membraneAminopeptidase NHomo sapiens (human)
secretory granule membraneAminopeptidase NHomo sapiens (human)
extracellular exosomeAminopeptidase NHomo sapiens (human)
cytoplasmAminopeptidase NHomo sapiens (human)
plasma membraneAminopeptidase NHomo sapiens (human)
extracellular spaceAminopeptidase NHomo sapiens (human)
extracellular regionDipeptidyl peptidase 4Homo sapiens (human)
lysosomal membraneDipeptidyl peptidase 4Homo sapiens (human)
plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
focal adhesionDipeptidyl peptidase 4Homo sapiens (human)
cell surfaceDipeptidyl peptidase 4Homo sapiens (human)
membraneDipeptidyl peptidase 4Homo sapiens (human)
apical plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
lamellipodiumDipeptidyl peptidase 4Homo sapiens (human)
endocytic vesicleDipeptidyl peptidase 4Homo sapiens (human)
lamellipodium membraneDipeptidyl peptidase 4Homo sapiens (human)
membrane raftDipeptidyl peptidase 4Homo sapiens (human)
intercellular canaliculusDipeptidyl peptidase 4Homo sapiens (human)
extracellular exosomeDipeptidyl peptidase 4Homo sapiens (human)
plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID38364Inhibitory activity against aminopeptidase N (APN) in human acute lymphoblastic leukemia MOLT-4 cell line1999Bioorganic & medicinal chemistry letters, Feb-22, Volume: 9, Issue:4
Nonpeptide small-molecular inhibitors of dipeptidyl peptidase IV: N-phenylphthalimide analogs.
AID257637Inhibitory activity in HUVEC tube formation assay at 30 uM2005Bioorganic & medicinal chemistry letters, Dec-15, Volume: 15, Issue:24
Angiogenesis inhibitors derived from thalidomide.
AID1057531Antiproliferative activity against human DU145 cells assessed as growth inhibition by MTS assay2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Structure-activity relationship studies of thalidomide analogs with a taxol-like mode of action.
AID448438Inhibition of NF-kappaB activation2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
The first pharmacophore model for potent NF-kappaB inhibitors.
AID257636Inhibitory activity in HUVEC tube formation assay at 100 uM2005Bioorganic & medicinal chemistry letters, Dec-15, Volume: 15, Issue:24
Angiogenesis inhibitors derived from thalidomide.
AID251886Cell growth-inhibitory activity toward human leukemia cell line HL60 at 10 uM concentration2005Bioorganic & medicinal chemistry letters, Jan-17, Volume: 15, Issue:2
Tubulin-polymerization inhibitors derived from thalidomide.
AID1057532Antiproliferative activity against human PC3 cells assessed as growth inhibition by MTS assay2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Structure-activity relationship studies of thalidomide analogs with a taxol-like mode of action.
AID219416Cytotoxicity in human embryonic lung flbroblast Wl-38 cells using WST-1 viability assay1999Bioorganic & medicinal chemistry letters, Feb-22, Volume: 9, Issue:4
Nonpeptide small-molecular inhibitors of dipeptidyl peptidase IV: N-phenylphthalimide analogs.
AID1057529Induction of purified porcine brain tubulin polymerization at 50 uM by spectrophotometric analysis2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Structure-activity relationship studies of thalidomide analogs with a taxol-like mode of action.
AID251661Inhibitory activity against tubulin polymerization at 20 uM2005Bioorganic & medicinal chemistry letters, Jan-17, Volume: 15, Issue:2
Tubulin-polymerization inhibitors derived from thalidomide.
AID81272Tumor necrosis factor-alpha production in human leukemia cell line (HL-60) stimulated with 50 nM okadaic acid (OA), at 30 uMolar.1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
Novel biological response modifiers: phthalimides with tumor necrosis factor-alpha production-regulating activity.
AID56226Inhibitory activity against Dipeptidylpeptidase IV (DPP IV) in human acute lymphoblastic leukemia MOLT-4 cell line1999Bioorganic & medicinal chemistry letters, Feb-22, Volume: 9, Issue:4
Nonpeptide small-molecular inhibitors of dipeptidyl peptidase IV: N-phenylphthalimide analogs.
AID252627NBT positivity against human leukemia cell line HL-60 at 1*E-5 M2005Bioorganic & medicinal chemistry letters, Jul-01, Volume: 15, Issue:13
Cell differentiation inducers derived from thalidomide.
AID56211Inhibitory activity against dipeptidyl peptidase IV (DPP- IV)1998Journal of medicinal chemistry, Jan-29, Volume: 41, Issue:3
Novel potent nonpeptide aminopeptidase N inhibitors with a cyclic imide skeleton.
AID38377Inhibitory activity against aminopeptidase N assayed by the L-Ala-MCA method.1998Journal of medicinal chemistry, Jan-29, Volume: 41, Issue:3
Novel potent nonpeptide aminopeptidase N inhibitors with a cyclic imide skeleton.
AID251888Cell growth-inhibitory activity toward human leukemia cell line HL60 at 6 uM concentration2005Bioorganic & medicinal chemistry letters, Jan-17, Volume: 15, Issue:2
Tubulin-polymerization inhibitors derived from thalidomide.
AID309667Inhibition of IL-1-alpha-induced NF-kappaB activation in HeLa cells assessed as blocking of p50/p65 nuclear translocation2007Bioorganic & medicinal chemistry letters, Nov-01, Volume: 17, Issue:21
Inhibitors of NF-kappaB derived from thalidomide.
AID218283The cytotoxicity of the compounds assessed using human embryonic lung fibroblast WI-38 cells at (53 micro M)1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
Novel biological response modifiers: phthalimides with tumor necrosis factor-alpha production-regulating activity.
AID1057530Antiproliferative activity against human MDA-MB-231 cells assessed as growth inhibition by MTS assay2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Structure-activity relationship studies of thalidomide analogs with a taxol-like mode of action.
AID81275Tumor necrosis factor-alpha production in human leukemia cell line (HL-60) stimulated with 10 nM 12-O-tetradecanoylphorbol 13-acetate (TPA) at 30 uMolar.1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
Novel biological response modifiers: phthalimides with tumor necrosis factor-alpha production-regulating activity.
AID257638Inhibitory activity in HUVEC tube formation assay at 10 uM2005Bioorganic & medicinal chemistry letters, Dec-15, Volume: 15, Issue:24
Angiogenesis inhibitors derived from thalidomide.
AID251887Cell growth-inhibitory activity toward human leukemia cell line HL60 at 3 uM concentration2005Bioorganic & medicinal chemistry letters, Jan-17, Volume: 15, Issue:2
Tubulin-polymerization inhibitors derived from thalidomide.
AID252970Percent cell proliferation of human leukemia cell line HL-60 at 1*E-5 M2005Bioorganic & medicinal chemistry letters, Jul-01, Volume: 15, Issue:13
Cell differentiation inducers derived from thalidomide.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (23.08)18.2507
2000's5 (38.46)29.6817
2010's4 (30.77)24.3611
2020's1 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.98

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 Index11.98 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.62 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.98)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]