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【结 构 式】

【药物名称】

【化学名称】4-(3-Phenyl-1H-indol-2-yl)benzenesulfonamide

【CA登记号】

【 分 子 式 】C20H16N2O2S

【 分 子 量 】348.42672

【开发单位】Chinese Academy of Medical Sciences (Originator), Peking Union Medical College (Originator)

【药理作用】Antiarthritic Drugs, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Cyclooxygenase-2 Inhibitors

合成路线1

Sulfonylation of anthranilic acid (I) with p-toluenesulfonyl chloride under Schotten-Baumann conditions furnishes N-tosyl anthranilic acid (II). After conversion of acid (II) to the corresponding acid chloride (III), Friedel-Crafts condensation with benzene in the presence of AlCl3 leads to the benzophenone (IV). The N-tosyl group of (IV) is then removed upon heating with concentrated sulfuric acid to provide 2-aminobenzophenone (V). Acylation of amine (V) with 4-(aminosulfonyl)benzoyl chloride (VI) yields amide (VII). This is finally cyclized to the target indole compound under McMurry conditions employing an in situ generated low valent titanium reagent.

1 Hu, W.; Guo, Z.; Chu, F.; Bai, A.; Yi, X.; Cheng, G.; Li, J.; Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: A new series of selective COX-2 inhibitors. Bioorg Med Chem 2003, 11, 7, 1153.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 11661 2-Aminobenzoic acid;Anthranilic acid; o-Aminobenzoic acid 118-92-3 C7H7NO2 详情 详情
(II) 64968 2-{[(4-methylphenyl)sulfonyl]amino}benzoic acid C14H13NO4S 详情 详情
(III) 64969 2-{[(4-methylphenyl)sulfonyl]amino}benzoyl chloride C14H12ClNO3S 详情 详情
(IV) 64970 4-methyl-N-[2-(phenylcarbonyl)phenyl]benzenesulfonamide C20H17NO3S 详情 详情
(V) 21101 (2-aminophenyl)(phenyl)methanone; 2-Aminobenzophenone 2835-77-0 C13H11NO 详情 详情
(VI) 64971 4-(aminosulfonyl)benzoyl chloride C7H6ClNO3S 详情 详情
(VII) 64972 4-(aminosulfonyl)-N-[2-(phenylcarbonyl)phenyl]benzamide C20H16N2O4S 详情 详情
Extended Information