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

• ChemBase ID: 153836
• Molecular Formular: C24H20ClN3O3
• Molecular Mass: 433.8869
• Monoisotopic Mass: 433.1193192
• SMILES: Cc1c(c2cc(ccc2n1C(=O)c1ccc(cc1)Cl)OC)CC(=O)Nc1cccnc1
• Canonical SMILES: COc1ccc2c(c1)c(CC(=O)Nc1cccnc1)c(n2C(=O)c1ccc(cc1)Cl)C
• InChI: InChI=1S/C24H20ClN3O3/c1-15-20(13-23(29)27-18-4-3-11-26-14-18)21-12-19(31-2)9-10-22(21)28(15)24(30)16-5-7-17(25)8-6-16/h3-12,14H,13H2,1-2H3,(H,27,29)
• InChIKey: DTAPHQYAZUTCIG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 261755-29-4
• MDL Number: MFCD02683393
• PubChem SID: 162247975
• PubChem CID: 4434869

CALCULATED PROPERTIES

• Acid pKa: 12.550665
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.7177742
• LogD (pH = 7.4): 3.7459269
• Log P: 3.7463038
• Molar Refractivity: 120.931 cm^3
• Polarizability: 46.714943 Å^3
• Polar Surface Area: 73.22 Å^2
• Rotatable Bonds: 5
• 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

• Purity: ≥98%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C24H20N3O3Cl

DETAILS

Sigma Aldrich - P0865

Biochem/physiol Actions
Potent and selective reversible cyclooxygenase-2 (COX-2) inhibitor (IC50 = 0.1 μM, human recombinant); about 300-fold less potent as an inhibitor of human recombinant COX-1. Not as selective with natural ovine COX (IC50 = 75 μM for COX-1 and 50 μM for COX-2).

Toronto Research Chemicals - P995375

An aromatic amide of indomethacin recently reported to be a potent and selective reversible inhibitor of COX-2. Inhibits human recombinant COX-2 with IC50 of 0.1 uM.

REFERENCES

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