2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(2-phenylethyl)acetamide

• ChemBase ID: 155663
• Molecular Formular: C27H25ClN2O3
• Molecular Mass: 460.952
• Monoisotopic Mass: 460.15537035
• SMILES: Cc1c(c2cc(ccc2n1C(=O)c1ccc(cc1)Cl)OC)CC(=O)NCCc1ccccc1
• Canonical SMILES: COc1ccc2c(c1)c(CC(=O)NCCc1ccccc1)c(n2C(=O)c1ccc(cc1)Cl)C
• InChI: InChI=1S/C27H25ClN2O3/c1-18-23(17-26(31)29-15-14-19-6-4-3-5-7-19)24-16-22(33-2)12-13-25(24)30(18)27(32)20-8-10-21(28)11-9-20/h3-13,16H,14-15,17H2,1-2H3,(H,29,31)
• InChIKey: VYDBTNADENXYSN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(2-phenylethyl)acetamide
• IUPAC Traditional name: 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-N-(2-phenylethyl)acetamide
• Synonyms: N-(2-Phenylethyl)-1-p-chlorobenzoyl-5-methoxy-2-methylindole-3-acetamide; 1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-N-(2-phenylethyl)-1H-indole-3-acetamide; N-(2-Phenylethyl)indomethacin Amide; N-(2-Phenylethyl)indomethacinamide

Database IDs

• CAS Number: 261766-32-9
• MDL Number: MFCD02683391
• PubChem SID: 162249801
• PubChem CID: 4292

CALCULATED PROPERTIES

• Acid pKa: 15.091862
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.9595423
• LogD (pH = 7.4): 4.9595423
• Log P: 4.9595423
• Molar Refractivity: 130.8971 cm^3
• Polarizability: 51.31554 Å^3
• Polar Surface Area: 60.33 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Shipped in: wet ice
• Empirical Formula (Hill Notation): C27H25N2O3Cl

DETAILS

Sigma Aldrich - P0740

Biochem/physiol Actions
Inhibits human recombinant and ovine cyclooxygenase-2 (COX-2) with IC50s of 0.06 μM and 0.125 μM, respectively; over 400-fold less potent as an inhibitor of COX-1.

Toronto Research Chemicals - P321250

An aromatic amide of indomethacin recently reported to be a potent and selective reversible inhibitor of COX-2. Inhibits human recombinant and ovine COX-2 with IC50 of 0.06 uM and 0.125 uM, respectively.

REFERENCES

• Kalgutkar, A.S., et al.: J. Med. Chem., 43, 2860 (2000)