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

• ChemBase ID: 155694
• Molecular Formular: C27H24ClN3O4
• Molecular Mass: 489.95016
• Monoisotopic Mass: 489.14553394
• SMILES: Cc1c(c2cc(ccc2n1C(=O)c1ccc(cc1)Cl)OC)CC(=O)Nc1ccc(cc1)NC(=O)C
• Canonical SMILES: COc1ccc2c(c1)c(CC(=O)Nc1ccc(cc1)NC(=O)C)c(n2C(=O)c1ccc(cc1)Cl)C
• InChI: InChI=1S/C27H24ClN3O4/c1-16-23(15-26(33)30-21-10-8-20(9-11-21)29-17(2)32)24-14-22(35-3)12-13-25(24)31(16)27(34)18-4-6-19(28)7-5-18/h4-14H,15H2,1-3H3,(H,29,32)(H,30,33)
• InChIKey: CVMUUPNNEPVQCL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 261766-23-8
• MDL Number: MFCD02683236
• PubChem SID: 162249832
• PubChem CID: 4090966

CALCULATED PROPERTIES

• Acid pKa: 13.961621
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.201687
• LogD (pH = 7.4): 4.2016864
• Log P: 4.201687
• Molar Refractivity: 137.9509 cm^3
• Polarizability: 52.492363 Å^3
• Polar Surface Area: 89.43 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: ≥23 mg/mL; DMSO: ≥15 mg/mL
• Apperance: crystalline; Pale Yellow Solid
• Melting Point: 256-257°C
• Absorption Wavelength: λmax 267 nm

Safety Information

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

Product Information

• Purity: ≥98%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C27H24N3O4Cl

DETAILS

Sigma Aldrich - A1224

Biochem/physiol Actions
Potent and selective reversible COX-2 inhibitor. N-4-AcetIA inhibits human and ovine COX-2 with IC50 of 0.1 μM and 0.625 μM, respectively. About 400 times less potent as an inhibitor of human COX-1 and 80 times less potent as an inhibitor of ovine COX-1. Shows anti-inflammatory, antiangiogenic, and cancer chemopreventive activity in various experimental models.

Toronto Research Chemicals - A161150

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 0.1 uM and 0.625 uM, respectively.

REFERENCES

• Kalgutkar, A.S., et al.: J. Med. Chem., 43, 2860 (2000)
• Holt, S., et al.: Eur. J. Pharmacol., 565, 26 (2000)