2-[(3R,4S)-3,4-bis(hydroxymethyl)-3,4-dimethylpyrrolidin-1-yl]-N-[3-carbamoyl-1-(4-fluorophenyl)-1H,4H,5H-benzo[g]indazol-8-yl]-5-chloropyridine-4-carboxamide

• ChemBase ID: 176417
• Molecular Formular: C32H32ClFN6O4
• Molecular Mass: 619.0856832
• Monoisotopic Mass: 618.21575943
• SMILES: C1Cc2c(cc(cc2)NC(=O)c2cc(ncc2Cl)N2C[C@]([C@](C2)(CO)C)(CO)C)c2c1c(nn2c1ccc(cc1)F)C(=O)N
• Canonical SMILES: OC[C@]1(C)CN(C[C@]1(C)CO)c1ncc(c(c1)C(=O)Nc1ccc2c(c1)c1c(CC2)c(nn1c1ccc(cc1)F)C(=O)N)Cl
• InChI: InChI=1S/C32H32ClFN6O4/c1-31(16-41)14-39(15-32(31,2)17-42)26-12-24(25(33)13-36-26)30(44)37-20-7-3-18-4-10-22-27(29(35)43)38-40(28(22)23(18)11-20)21-8-5-19(34)6-9-21/h3,5-9,11-13,41-42H,4,10,14-17H2,1-2H3,(H2,35,43)(H,37,44)/t31-,32+
• InChIKey: JUOWWGNRWRLBSV-MEKGRNQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3R,4S)-3,4-bis(hydroxymethyl)-3,4-dimethylpyrrolidin-1-yl]-N-[3-carbamoyl-1-(4-fluorophenyl)-1H,4H,5H-benzo[g]indazol-8-yl]-5-chloropyridine-4-carboxamide
• IUPAC Traditional name: 2-[(3R,4S)-3,4-bis(hydroxymethyl)-3,4-dimethylpyrrolidin-1-yl]-N-[3-carbamoyl-1-(4-fluorophenyl)-4H,5H-benzo[g]indazol-8-yl]-5-chloropyridine-4-carboxamide
• Synonyms: 8-[[[5-Chloro-2-[3,4-dimethyl-3,4-bis(hydroxymethyl)-1-pyrrolidinyl]-4-pyridinyl]carbonyl]amino]-1-(4-fluorophenyl)-4,5-dihydro-1H-benz[g]indazole-3-carboxamide; PF 184

Database IDs

• CAS Number: 1187460-81-6
• PubChem SID: 164232327
• PubChem CID: 57519531

CALCULATED PROPERTIES

• Acid pKa: 11.086457
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 4.079477
• LogD (pH = 7.4): 4.0794754
• Log P: 4.079561
• Molar Refractivity: 168.3897 cm^3
• Polarizability: 63.655045 Å^3
• Polar Surface Area: 146.6 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P293750

PF 184 is a potent and selective IKK-2 inhibitor (IC50 = 37 nM). Displays selectivity over 85 other kinases. Inhibits IL-1β-induced TNF-α in a steroid-insensitive in vitro model of oxidative stress.

REFERENCES

• Baldwin, A., et al.: J. Clin. Invest., 107, 3 (2001)
• Adcock, I., et al.: Eur. J. Pharmacol., 533, 118 (2001)
• Sommers, et al.: J. Pharmacol. Exp. Ther., 330 377 (2001)