4-(4-{[2-(4-chlorophenyl)phenyl]methyl}(2H8)piperazin-1-yl)-N-(4-{[(2R)-4-(dimethylamino)-1-(phenylsulfanyl)butan-2-yl]amino}-3-nitrobenzenesulfonyl)benzamide

• ChemBase ID: 158821
• Molecular Formular: C42H45ClN6O5S2
• Molecular Mass: 813.4269
• Monoisotopic Mass: 812.25813825
• SMILES: c1cc(c(cc1)CN1CCN(CC1)c1ccc(cc1)C(=O)NS(=O)(=O)c1cc(c(cc1)N[C@H](CCN(C)C)CSc1ccccc1)[N+](=O)[O-])c1ccc(cc1)Cl
• Canonical SMILES: CN(CC[C@@H](Nc1ccc(cc1[N+](=O)[O-])S(=O)(=O)NC(=O)c1ccc(cc1)N1CCN(CC1)Cc1ccccc1c1ccc(cc1)Cl)CSc1ccccc1)C
• InChI: InChI=1S/C42H45ClN6O5S2/c1-46(2)23-22-35(30-55-37-9-4-3-5-10-37)44-40-21-20-38(28-41(40)49(51)52)56(53,54)45-42(50)32-14-18-36(19-15-32)48-26-24-47(25-27-48)29-33-8-6-7-11-39(33)31-12-16-34(43)17-13-31/h3-21,28,35,44H,22-27,29-30H2,1-2H3,(H,45,50)/t35-/m1/s1
• InChIKey: HPLNQCPCUACXLM-PGUFJCEWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(4-{[2-(4-chlorophenyl)phenyl]methyl}(^2H₈)piperazin-1-yl)-N-(4-{[(2R)-4-(dimethylamino)-1-(phenylsulfanyl)butan-2-yl]amino}-3-nitrobenzenesulfonyl)benzamide
• IUPAC Traditional name: 4-(4-{[2-(4-chlorophenyl)phenyl]methyl}(^2H₈)piperazin-1-yl)-N-(4-{[(2R)-4-(dimethylamino)-1-(phenylsulfanyl)butan-2-yl]amino}-3-nitrobenzenesulfonyl)benzamide
• Synonyms: 4-[4-[(4’-Chloro[1,1’-biphenyl]-2-yl)methyl]-1-piperazinyl]-N-[[4-[[(1R)-3-(dimethylamino)-1-[(phenylthio)methyl]propyl]amino]-3-nitrophenyl]sulfonyl]benzamide-d8; ABT 737-d8

Database IDs

• PubChem SID: 162252956
• PubChem CID: 46779841

CALCULATED PROPERTIES

• Acid pKa: 4.2773795
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): 4.559849
• LogD (pH = 7.4): 6.3591967
• Log P: 7.4634604
• Molar Refractivity: 230.6089 cm^3
• Polarizability: 88.6396 Å^3
• Polar Surface Area: 130.81 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: 148-150°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A112552

A selective inhibitor of BCL-2, in small cell lung cancer. ABT-737 induced dramatic regressions in tumors derived from some SCLC cell lines.

REFERENCES

• Ikegaki, N., et al.: Cancer Res., 54, 6 (1994)
• Kaiser, U., et al.: Lung Cancer, 15, 31 (1994)
• Rudin, C., et al.: J. Clin. Oncol., 22, 1110 ( 2004), Konopleva, M., et al.: Cancer Cell, 10, 375 (1994)
• Trudel, S., et al.: Clin. Cancer Res., 13, 621 (2007)