2-{6-chloro-5-[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazine-1-carbonyl]-1-methyl-1H-indol-3-yl}-N,N-dimethyl-2-oxoacetamide

• ChemBase ID: 177983
• Molecular Formular: C27H30ClFN4O3
• Molecular Mass: 513.0035032
• Monoisotopic Mass: 512.19904674
• SMILES: c1(ccc(cc1)CN1C[C@H](N(C[C@@H]1C)C(=O)c1c(cc2c(c1)c(cn2C)C(=O)C(=O)N(C)C)Cl)C)F
• Canonical SMILES: Fc1ccc(cc1)CN1C[C@@H](C)N(C[C@@H]1C)C(=O)c1cc2c(cn(c2cc1Cl)C)C(=O)C(=O)N(C)C
• InChI: InChI=1S/C27H30ClFN4O3/c1-16-13-33(17(2)12-32(16)14-18-6-8-19(29)9-7-18)26(35)21-10-20-22(25(34)27(36)30(3)4)15-31(5)24(20)11-23(21)28/h6-11,15-17H,12-14H2,1-5H3/t16-,17+/m0/s1
• InChIKey: ZMELOYOKMZBMRB-DLBZAZTESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{6-chloro-5-[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazine-1-carbonyl]-1-methyl-1H-indol-3-yl}-N,N-dimethyl-2-oxoacetamide
• IUPAC Traditional name: talmapimod
• Synonyms: 6-Chloro-5-[[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethyl-1-piperazinyl]carbonyl]-N,N,1-trimethyl-α-oxo-1H-indole-3-acetamide; SCIO 469; Scios 469; Talmapimod

Database IDs

• CAS Number: 309913-83-5
• PubChem SID: 164233893
• PubChem CID: 9871074

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.3196385
• LogD (pH = 7.4): 3.887601
• Log P: 3.9028168
• Molar Refractivity: 139.2478 cm^3
• Polarizability: 53.59113 Å^3
• Polar Surface Area: 65.86 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T005550

Talmapimod is a p38 mitogen-activated protein (MAP) kinase inhibitor. Talmapimod reduced human myeloma cell growth in vivo both at early and advanced phases of the disease in mouse xenograft models. Talmapimod that blocks tumor necrosis factor-α, interleu

REFERENCES

• Medicherla, S. et al.: Antincancer Res., 28, 3827 (2008)
• Genovese, M.S. et al.: J. Rheumatol., 38, 846 (2008)
• Medicherla, S. et al.: J. Inflam. Res., 3, 9 (2008)