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CHEBI:167655 - BMS-214662

ChEBI IDCHEBI:167655
ChEBI NameBMS-214662
Stars
DefinitionA member of the class of benzodiazepines that is 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine substituted by (1H-imidazol-5-yl)methyl, benzyl, (thiophen-2-yl)sulfonyl, and cyano groups at positions 1, 3R, 4 and 7, respectively. It is a potent inhibitor of farnesyltransferase (IC50 = 1.35nM) which was under clinical development for the treatment of solid tumors.
Last Modified18 March 2021
SubmitterR. Stephan
DownloadsMolfile
FormulaC25H23N5O2S2
Net Charge0
Average Mass489.626
Monoisotopic Mass489.12932
SMILESN#Cc1ccc2c(c1)CN(S(=O)(=O)c1cccs1)[C@H](Cc1ccccc1)CN2Cc1cncn1
InChIInChI=1S/C25H23N5O2S2/c26-13-20-8-9-24-21(11-20)15-30(34(31,32)25-7-4-10-33-25)23(12-19-5-2-1-3-6-19)17-29(24)16-22-14-27-18-28-22/h1-11,14,18,23H,12,15-17H2,(H,27,28)/t23-/m1/s1
InChIKeyOLCWFLWEHWLBTO-HSZRJFAPSA-N
Roles Classification
Biological Roles:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 2.5.1.58 (protein farnesyltransferase) inhibitor  An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of protein farnesyltransferase (EC 2.5.1.58), one of the three enzymes in the prenyltransferase group.
GABA modulator  A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
GABA modulator  A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
ChEBI Ontology
Outgoing Relation(s)
BMS-214662 (CHEBI:167655) has role antineoplastic agent (CHEBI:35610)
BMS-214662 (CHEBI:167655) has role apoptosis inducer (CHEBI:68495)
BMS-214662 (CHEBI:167655) has role EC 2.5.1.58 (protein farnesyltransferase) inhibitor (CHEBI:64133)
BMS-214662 (CHEBI:167655) is a benzenes (CHEBI:22712)
BMS-214662 (CHEBI:167655) is a benzodiazepine (CHEBI:22720)
BMS-214662 (CHEBI:167655) is a imidazoles (CHEBI:24780)
BMS-214662 (CHEBI:167655) is a nitrile (CHEBI:18379)
BMS-214662 (CHEBI:167655) is a sulfonamide (CHEBI:35358)
BMS-214662 (CHEBI:167655) is a thiophenes (CHEBI:26961)
IUPAC Name 
(3R)-3-benzyl-1-(1H-imidazol-5-ylmethyl)-4-(thiophen-2-ylsulfonyl)-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile
Synonyms  Source
(3R)-3-benzyl-1-(1H-imidazol-5-ylmethyl)-4-thiophen-2-ylsulfonyl-3,5-dihydro-2H-1,4-benzodiazepine-7-carbonitrileChEBI
BMS214662ChemIDplus
BMS 214662ChemIDplus
(R)-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-3-(phenylmethyl)-4-(2-thienylsulfonyl)-1H-1,4-benzodiazepine-7-carbonitrileChEBI
(R)-7-cyano-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-3-(phenylmethyl)-4-(2-thienylsulfonyl)-1H-1,4-benzodiazepineChEBI
Manual XrefsDatabases
DB12234DrugBank
BMVPDBeChem
395310ChemSpider
Registry NumbersSources
CAS:195987-41-8ChemIDplus
Citations