Page last updated: 2024-11-13

cyclopentylidene-[4-(4-chlorophenyl)thiazol-2-yl]hydrazone

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Description

cyclopentylidene-[4-(4-chlorophenyl)thiazol-2-yl]hydrazone : A member of the class of 1,3-thiazole bearing 2-cyclopentylidenehydrazino and 4-chlorophenyl substituents at positions 2 and 4 respectively. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID25193530
CHEMBL ID246811
CHEBI ID77993
SCHEMBL ID17144584

Synonyms (28)

Synonym
chebi:77993 ,
CHEMBL246811 ,
4-(4-chlorophenyl)-2-(2-cyclopentylidenehydrazinyl)thiazole
bdbm50326625
1-(4-(4-chlorophenyl)thiazol-2-yl)-2-cyclopentylidenehydrazine
cyclopentylidene-[ 4-(4''-chlorophenyl)thiazol-2-yl)hydrazone
cpth2
357649-93-5
S1242
cyclopentylidene-[4-(4-chlorophenyl)thiazol-2-yl]hydrazone
4-(4-chlorophenyl)-2-(2-cyclopentylidenehydrazino)-1,3-thiazole
mfcd02307488
DTXSID90649008
4-(4-chlorophenyl)-2-(2-cyclopentylidenehydrazinyl)-1,3-thiazole
SCHEMBL17144584
histone acetyltransferase inhibitor iv, cpth2
cpth2, >=98% (hplc), powder
AKOS027250781
4-(4-chlorophenyl)-2-(2-cyclopentylidenehydrazineyl)thiazole
CS-W013990
Q27147576
histone acetyltransferase inhibitor iv, cpth2 - cas 357649-93-5
CS-17365
D72189
n-[4-(4-chloro-phenyl)-thiazol-2-yl]-n'-cyclopentylidene-hydrazine
HY-W013274
EX-A5955
4-(4-chlorophenyl)-n-(cyclopentylideneamino)-1,3-thiazol-2-amine
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
EC 2.3.1.48 (histone acetyltransferase) inhibitorAn EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the function of histone acetyltransferase (EC 2.3.1.48).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
1,3-thiazoles
hydrazoneCompounds having the structure R2C=NNR2, formally derived from aldehydes or ketones by replacing =O by =NNH2 (or substituted analogues).
monochlorobenzenesAny member of the class of chlorobenzenes containing a mono- or poly-substituted benzene ring in which only one substituent is chlorine.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Amine oxidase [flavin-containing] AHomo sapiens (human)IC50 (µMol)7.20220.00002.37899.7700AID514141
Amine oxidase [flavin-containing] BHomo sapiens (human)IC50 (µMol)0.26250.00001.89149.5700AID514142
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (15)

Processvia Protein(s)Taxonomy
biogenic amine metabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
positive regulation of signal transductionAmine oxidase [flavin-containing] AHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
response to xenobiotic stimulusAmine oxidase [flavin-containing] BHomo sapiens (human)
response to toxic substanceAmine oxidase [flavin-containing] BHomo sapiens (human)
response to aluminum ionAmine oxidase [flavin-containing] BHomo sapiens (human)
response to selenium ionAmine oxidase [flavin-containing] BHomo sapiens (human)
negative regulation of serotonin secretionAmine oxidase [flavin-containing] BHomo sapiens (human)
phenylethylamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
substantia nigra developmentAmine oxidase [flavin-containing] BHomo sapiens (human)
response to lipopolysaccharideAmine oxidase [flavin-containing] BHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to ethanolAmine oxidase [flavin-containing] BHomo sapiens (human)
positive regulation of dopamine metabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
hydrogen peroxide biosynthetic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to corticosteroneAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
protein bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
electron transfer activityAmine oxidase [flavin-containing] BHomo sapiens (human)
identical protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] AHomo sapiens (human)
cytosolAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial envelopeAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] BHomo sapiens (human)
dendriteAmine oxidase [flavin-containing] BHomo sapiens (human)
neuronal cell bodyAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (40)

Assay IDTitleYearJournalArticle
AID514142Inhibition of human recombinant MAOB expressed in baculovirus infected BTI-TN-5B1-4 insect cells assessed as hydrogen peroxide production from p-tyramine by amplex red assay2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors.
AID411271Growth inhibition of wild type wild type Saccharomyces cerevisiae SB819 at 0.2 to 1 mM after 48 hrs at 28 degC by growth spot assay2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID1067291Growth inhibition of Saccharomyces cerevisiae BY4742 harboring gcn5delta mutant at 0.5 mM after 48 hrs2014Bioorganic & medicinal chemistry, Mar-01, Volume: 22, Issue:5
Synthesis of a novel series of thiazole-based histone acetyltransferase inhibitors.
AID1143395Inhibition of recombinant human p300 catalytic domain (1284 to 1673 aa) using histone H3 at 100 uM after 1 hr by radiochemical assay in presence of [acetyl-3H]-acetyl coenzyme A2014European journal of medicinal chemistry, Jun-10, Volume: 80Evaluation of a large library of (thiazol-2-yl)hydrazones and analogues as histone acetyltransferase inhibitors: enzyme and cellular studies.
AID514141Inhibition of human recombinant MAOA expressed in baculovirus infected BTI-TN-5B1-4 insect cells assessed as hydrogen peroxide production from p-tyramine by amplex red assay2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors.
AID308421Antifungal activity against Candida albicans after 24 hrs by broth microdilution method2007Bioorganic & medicinal chemistry letters, Aug-15, Volume: 17, Issue:16
Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp.
AID411275Inhibition of human recombinant Gcn5 assessed as reduction in acetylated histone H3 level at 0.8 mM by Western blot analysis in presence of 200 ng histone H32009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID411276Inhibition of human recombinant Gcn5 assessed as reduction in acetylated histone H3 level at 0.8 mM by Western blot analysis in presence of increased concentration of acetyl-CoA2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID1067295Reduction of growth of Saccharomyces cerevisiae harboring gcn5delta mutant at 0.5 mM after 48 hrs2014Bioorganic & medicinal chemistry, Mar-01, Volume: 22, Issue:5
Synthesis of a novel series of thiazole-based histone acetyltransferase inhibitors.
AID308429Cytotoxicity against human EAhy926 cells assessed as cell survival fraction at 0.5 ug/ml after 24 hrs by trypan blue exclusion test2007Bioorganic & medicinal chemistry letters, Aug-15, Volume: 17, Issue:16
Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp.
AID308428Cytotoxicity against human EAhy926 cells assessed as cell survival fraction at 5 ug/ml after 24 hrs by trypan blue exclusion test2007Bioorganic & medicinal chemistry letters, Aug-15, Volume: 17, Issue:16
Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp.
AID308427Cytotoxicity against human EAhy926 cells assessed as cell survival fraction at 50 ug/ml after 24 hrs by trypan blue exclusion test2007Bioorganic & medicinal chemistry letters, Aug-15, Volume: 17, Issue:16
Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp.
AID1067292Growth inhibition of Saccharomyces cerevisiae S288c harboring gcn5delta mutant at 0.5 mM after 48 hrs2014Bioorganic & medicinal chemistry, Mar-01, Volume: 22, Issue:5
Synthesis of a novel series of thiazole-based histone acetyltransferase inhibitors.
AID514145Selectivity ratio of IC50 for human recombinant MAOA to IC50 for human recombinant MAOB2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors.
AID1067288Growth inhibition of Saccharomyces cerevisiae S288c harboring elp3delta mutant at 0.5 mM after 48 hrs2014Bioorganic & medicinal chemistry, Mar-01, Volume: 22, Issue:5
Synthesis of a novel series of thiazole-based histone acetyltransferase inhibitors.
AID411270Growth inhibition of Saccharomyces cerevisiae SB0-deltabr mutant at 0.2 to 1 mM after 48 hrs at 28 degC by growth spot assay2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID308422Antifungal activity against Candida glabrata after 24 hrs by broth microdilution method2007Bioorganic & medicinal chemistry letters, Aug-15, Volume: 17, Issue:16
Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp.
AID411269Growth inhibition of Saccharomyces cerevisiae gcn5E173H mutant at 0.2 to 1 mM after 48 hrs at 28 degC by growth spot assay2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID411272Inhibition of human recombinant Gcn5 assessed as reduction in acetylated histone H3 level at 0.8 mM by Western blot analysis2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID1143396Inhibition of recombinant human p300 catalytic domain (1284 to 1673 aa) using histone H3 at 200 uM after 1 hr by radiochemical assay in presence of [acetyl-3H]-acetyl coenzyme A2014European journal of medicinal chemistry, Jun-10, Volume: 80Evaluation of a large library of (thiazol-2-yl)hydrazones and analogues as histone acetyltransferase inhibitors: enzyme and cellular studies.
AID1067297Reduction of wild type Saccharomyces cerevisiae growth at 0.5 mM after 48 hrs2014Bioorganic & medicinal chemistry, Mar-01, Volume: 22, Issue:5
Synthesis of a novel series of thiazole-based histone acetyltransferase inhibitors.
AID411267Growth inhibition of Saccharomyces cerevisiae sas2delta mutant at 0.2 to 1 mM after 72 hrs at 28 degC by growth spot assay2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID1067287Growth inhibition of Saccharomyces cerevisiae BY4742 harboring rtt109delta mutant at 0.5 mM after 48 hrs2014Bioorganic & medicinal chemistry, Mar-01, Volume: 22, Issue:5
Synthesis of a novel series of thiazole-based histone acetyltransferase inhibitors.
AID411278Decrease in global histone H3 acetylation in wild type Saccharomyces cerevisiae S288C at 0.8 mM after 24 hrs at 28 degC by hybridization assay2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID411265Growth inhibition of Saccharomyces cerevisiae gcn5delta mutant at 0.2 to 1 mM after 72 hrs at 28 degC by growth spot assay2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID308430Cytotoxicity against human EAhy926 cells assessed as cell survival fraction at 0.05 ug/ml after 24 hrs by trypan blue exclusion test2007Bioorganic & medicinal chemistry letters, Aug-15, Volume: 17, Issue:16
Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp.
AID411282Inhibition of histone H3 acetylation at H3-AcK14 site in Saccharomyces cerevisiae gcn5delta mutant at 0.8 mM after 24 hrs at 28 degC by hybridization assay2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID1143398Inhibition of recombinant human PCAF catalytic domain (492 to 658 aa) using histone H3 at 100 uM after 1 hr by radiochemical assay in presence of [acetyl-3H]-acetyl coenzyme A2014European journal of medicinal chemistry, Jun-10, Volume: 80Evaluation of a large library of (thiazol-2-yl)hydrazones and analogues as histone acetyltransferase inhibitors: enzyme and cellular studies.
AID308425Antifungal activity against Candida parapsilosis after 24 hrs by broth microdilution method2007Bioorganic & medicinal chemistry letters, Aug-15, Volume: 17, Issue:16
Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp.
AID411281Inhibition of global histone H3 acetylation in Saccharomyces cerevisiae gcn5delta mutant at 0.8 mM after 24 hrs at 28 degC by hybridization assay2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID308424Antifungal activity against Candida krusei after 24 hrs by broth microdilution method2007Bioorganic & medicinal chemistry letters, Aug-15, Volume: 17, Issue:16
Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp.
AID1143397Inhibition of recombinant human p300 catalytic domain (1284 to 1673 aa) using histone H3 at 400 uM after 1 hr by radiochemical assay in presence of [acetyl-3H]-acetyl coenzyme A2014European journal of medicinal chemistry, Jun-10, Volume: 80Evaluation of a large library of (thiazol-2-yl)hydrazones and analogues as histone acetyltransferase inhibitors: enzyme and cellular studies.
AID411280Inhibition of histone H3 acetylation at H3-AcK14 site in wild type Saccharomyces cerevisiae S288C at 0.8 mM after 24 hrs at 28 degC by hybridization assay2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID1067286Growth inhibition of Saccharomyces cerevisiae S288c harboring sas2delta mutant at 0.5 mM after 48 hrs2014Bioorganic & medicinal chemistry, Mar-01, Volume: 22, Issue:5
Synthesis of a novel series of thiazole-based histone acetyltransferase inhibitors.
AID411268Growth inhibition of Saccharomyces cerevisiae gcn5delta mutant at 0.2 to 1 mM after 48 hrs at 28 degC by growth spot assay2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID411279Reduction of global histone H4 acetylation in wild type Saccharomyces cerevisiae S288C at 0.8 mM after 24 hrs at 28 degC by hybridization assay2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID411274Inhibition of human recombinant Gcn5 assessed as reduction in acetylated histone H3 level at 0.8 mM by Western blot analysis in presence of 100 ng histone H32009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
AID308423Antifungal activity against Candida tropicalis after 24 hrs by broth microdilution method2007Bioorganic & medicinal chemistry letters, Aug-15, Volume: 17, Issue:16
Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp.
AID308426Antifungal activity against Candida sake after 24 hrs by broth microdilution method2007Bioorganic & medicinal chemistry letters, Aug-15, Volume: 17, Issue:16
Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp.
AID411266Growth inhibition of Saccharomyces cerevisiae elp3delta mutant at 0.2 to 1 mM after 72 hrs at 28 degC by growth spot assay2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
A novel histone acetyltransferase inhibitor modulating Gcn5 network: cyclopentylidene-[4-(4'-chlorophenyl)thiazol-2-yl)hydrazone.
[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's2 (40.00)29.6817
2010's3 (60.00)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]