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

• ChemBase编号: 153836
• 分子式: C24H20ClN3O3
• 平均质量: 433.8869
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(pyridin-3-yl)acetamide
• IUPAC传统名: 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-N-(pyridin-3-yl)acetamide
• 别名: 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

登记号

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

理论计算性质

• Acid pKa: 12.550665
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 3.7177742
• LogD (pH = 7.4): 3.7459269
• Log P: 3.7463038
• 摩尔折射率: 120.931 cm^3
• 极化性: 46.714943 Å^3
• 极化表面积: 73.22 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98%
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C24H20N3O3Cl

详细说明

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.

参考文献

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