(3R)-3-benzyl-1-(1H-imidazol-5-ylmethyl)-4-(thiophene-2-sulfonyl)-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile

• ChemBase ID: 162456
• Molecular Formular: C25H23N5O2S2
• Molecular Mass: 489.61242
• Monoisotopic Mass: 489.129317
• SMILES: C1N(c2c(CN([C@@H]1Cc1ccccc1)S(=O)(=O)c1cccs1)cc(cc2)C#N)Cc1[nH]cnc1
• Canonical SMILES: N#Cc1ccc2c(c1)CN([C@@H](CN2Cc1[nH]cnc1)Cc1ccccc1)S(=O)(=O)c1cccs1
• InChI: InChI=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
• InChIKey: OLCWFLWEHWLBTO-HSZRJFAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-benzyl-1-(1H-imidazol-5-ylmethyl)-4-(thiophene-2-sulfonyl)-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile
• IUPAC Traditional name: (3R)-3-benzyl-1-(3H-imidazol-4-ylmethyl)-4-(thiophene-2-sulfonyl)-3,5-dihydro-2H-1,4-benzodiazepine-7-carbonitrile
• Synonyms: (3R)-2,3,4,5-Tetrahydro-1-(1H-imidazol-4-ylmethyl)-3-(phenylmethyl)-4-(2-thienylsulfonyl)-1H-1,4-benzodiazepine-7-carbonitrile; (R)-2,3,4,5-Tetrahydro-1-(1H-imidazol-4-ylmethyl)-3-(phenylmethyl)-4-(2-thienylsulfonyl)-1H-1,4-benzodiazepine-7-carbonitrile; BMS 214662

Database IDs

• CAS Number: 195987-41-8
• PubChem SID: 162256591
• PubChem CID: 448545

CALCULATED PROPERTIES

• Acid pKa: 12.605025
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.580996
• LogD (pH = 7.4): 4.0415087
• Log P: 4.0890603
• Molar Refractivity: 133.5515 cm^3
• Polarizability: 51.32949 Å^3
• Polar Surface Area: 93.09 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B596050

A potent and selective inhibitor of farnesyltransferase that induces mitochondrial apoptosis in chronic myeloid leukemia stem/progenitor cells, including CD34+38- cells, through activation of protein kinase Cβ.

REFERENCES

• Rose, W.C. et al.: Cancer Res., 61, 7507 (2001)
• Tabernero, J. et al.: J. Clin. Oncol., 23, 2521 (2001)
• Pellicano, F. et al.: Blood, 114, 4186 (2001)