4-[(5-{[(cyclopentyloxy)carbonyl]amino}-1-methyl-1H-indol-3-yl)methyl]-3-methoxybenzoic acid

• ChemBase ID: 165244
• Molecular Formular: C24H26N2O5
• Molecular Mass: 422.47364
• Monoisotopic Mass: 422.18417194
• SMILES: c1c(cc2c(c1)n(cc2Cc1c(cc(cc1)C(=O)O)OC)C)NC(=O)OC1CCCC1
• Canonical SMILES: COc1cc(ccc1Cc1cn(c2c1cc(cc2)NC(=O)OC1CCCC1)C)C(=O)O
• InChI: InChI=1S/C24H26N2O5/c1-26-14-17(11-15-7-8-16(23(27)28)12-22(15)30-2)20-13-18(9-10-21(20)26)25-24(29)31-19-5-3-4-6-19/h7-10,12-14,19H,3-6,11H2,1-2H3,(H,25,29)(H,27,28)
• InChIKey: KFQBKNCZRCRBOU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(5-{[(cyclopentyloxy)carbonyl]amino}-1-methyl-1H-indol-3-yl)methyl]-3-methoxybenzoic acid
• IUPAC Traditional name: 4-[(5-{[(cyclopentyloxy)carbonyl]amino}-1-methylindol-3-yl)methyl]-3-methoxybenzoic acid
• Synonyms: 4-[[5-[[(Cyclopentyloxy)carbonyl]amino]-1-methyl-1H-indol-3-yl]methyl]-3-methoxybenzoic Acid

Database IDs

• CAS Number: 107754-20-1
• PubChem SID: 162259377
• PubChem CID: 11293119

CALCULATED PROPERTIES

• Acid pKa: 3.9786804
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.5691319
• LogD (pH = 7.4): 1.9279212
• Log P: 5.099093
• Molar Refractivity: 118.3976 cm^3
• Polarizability: 45.694927 Å^3
• Polar Surface Area: 89.79 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Off-White Solid
• Melting Point: 203-209°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C988550

An intermediate of Zafirlukast (Z125000), as leukotriene antagonist.

REFERENCES

• Samuelsson, B., et al.: Science, 220, 568 (1983)
• Matassa, V.G., et al.: J. Med. Chem., 33, 1781 (1983)
• Wenzel, S., et al.: Pharmacotherapy, 17, 3S (1983)