ethyl (6S)-6-[(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

• ChemBase ID: 177400
• Molecular Formular: C15H17ClFNO4S
• Molecular Mass: 361.8161832
• Monoisotopic Mass: 361.05508493
• SMILES: C1=C([C@H](CCC1)S(=O)(=O)Nc1c(cc(cc1)F)Cl)C(=O)OCC
• Canonical SMILES: CCOC(=O)C1=CCCC[C@@H]1S(=O)(=O)Nc1ccc(cc1Cl)F
• InChI: InChI=1S/C15H17ClFNO4S/c1-2-22-15(19)11-5-3-4-6-14(11)23(20,21)18-13-8-7-10(17)9-12(13)16/h5,7-9,14,18H,2-4,6H2,1H3/t14-/m0/s1
• InChIKey: LEEIJTHMHDMWLJ-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (6S)-6-[(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate
• IUPAC Traditional name: ethyl (6S)-6-[(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate
• Synonyms: (6R)-6-[[(2-Chloro-4-fluorophenyl)amino]sulfonyl]-1-cyclohexene-1-carboxylic Acid Ethyl Ester; TAK 242; Resatorvid

Database IDs

• CAS Number: 243984-11-4
• PubChem SID: 164233310
• PubChem CID: 11545031

CALCULATED PROPERTIES

• Acid pKa: 7.1012225
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.1523502
• LogD (pH = 7.4): 2.7750437
• Log P: 3.1618557
• Molar Refractivity: 85.5037 cm^3
• Polarizability: 33.70718 Å^3
• Polar Surface Area: 72.47 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R144570

Resatorvid is a novel selective Toll-like receptor 4 signal transduction inhibitor. Resatorvid inhibits various kinds of inflammatory mediators such as nitric oxide (NO), tumor necrosis factor (TNF)-α, interleukin (IL)-1, IL-6, IL-10, macrophage inhibitor

REFERENCES

• Abraham, E., et al.: Lancet, 351, 929 (1998)
• Akashi, S., et al.: J. Exp. Med., 198, 1035 (1998)
• Akira, S., et al.: Immunol. Lett., 85, 85 (1998)
• Medvedev, A., et al.: J. Biol. Chem., 282, 16042 (1998)