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

• ChemBase编号: 155694
• 分子式: C27H24ClN3O4
• 平均质量: 489.95016
• 单一同位素质量: 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

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-(4-acetamidophenyl)acetamide
• IUPAC传统名: 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-N-(4-acetamidophenyl)acetamide
• 别名: 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

登记号

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

理论计算性质

• Acid pKa: 13.961621
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 4.201687
• LogD (pH = 7.4): 4.2016864
• Log P: 4.201687
• 摩尔折射率: 137.9509 cm^3
• 极化性: 52.492363 Å^3
• 极化表面积: 89.43 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMF: ≥23 mg/mL; DMSO: ≥15 mg/mL
• 外观: crystalline; Pale Yellow Solid
• 熔点: 256-257°C
• 紫外吸收波长: λmax 267 nm

安全信息

• 保存条件: -20°C Freezer
• 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): C27H24N3O4Cl

详细说明

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.

参考文献

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