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【结 构 式】 
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【药物名称】Indisulam, E-7070, ER-35744 【化学名称】N-(3-Chloroindol-7-yl)benzene-1,4-disulfonamide 【CA登记号】165668-41-7 【 分 子 式 】C14H12ClN3O4S2 【 分 子 量 】385.85044 |
【开发单位】Eisai (Originator), Abbott (Licensee) 【药理作用】Breast Cancer Therapy, Colorectal Cancer Therapy, Head and Neck Cancer Therapy, Lung Cancer Therapy, Melanoma Therapy, Non-Small Cell Lung Cancer Therapy, Oncolytic Drugs, Apoptosis Inducers, Carbonic Anhydrase Type I Inhibitors, Carbonic Anhydrase Type II Inhibitors, Carbonic Anhydrase Type IX Inhibitors, CDK2 Inhibitors, Cyclin E Inhibitors, Inhibitors of Signal Transduction Pathways |
合成路线1
The reaction of 7-nitro-1H-indole (I) with NCS in acetonitrile gives 3-chloro-7-nitro-1H-indole (II), which is reduced with Fe and NH4Cl or stannous chloride in ethanol/aq. HCl to yield 3-chloro-1H-indol-7-amine (III). Finally, this compound is condensed with 4-sulfamoylbenzenesulfonyl chloride (IV) in pyridine to afford the target sulfonamide. The intermediate 4-sulfamoylbenzenesulfonyl chloride (IV) is obtained by diazotation of 4-aminobenzenesulfonamide (V) with NaNo2 and HCl, followed by treatment with SO2 and CuCl2.
| 【1】 Yoshino, H.; Yamato, T.; Okauchi, T.; Yoshimatsu, K.; Sugi, N.; Nagasu, T.; Ozawa, Y.; Koyanagi, N.; Kito, K. (Eisai Co., Ltd.); Bicyclic heterocyclic sulfonamide and sulfonic ester derivs.. EP 0673937; US 5721246; WO 9507276 . |
| 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) | 54715 | 7-Nitroindole | 6960-42-5 | C8H6N2O2 | 详情 | 详情 |
| (II) | 54716 | 3-chloro-7-nitro-1H-indole | C8H5ClN2O2 | 详情 | 详情 | |
| (III) | 54717 | 3-chloro-1H-indol-7-amine; 3-chloro-1H-indol-7-ylamine | C8H7ClN2 | 详情 | 详情 | |
| (IV) | 54718 | 4-(aminosulfonyl)benzenesulfonyl chloride | C6H6ClNO4S2 | 详情 | 详情 | |
| (V) | 54719 | 4-Aminobenzenesulfonamide; p-Aminobenzene sulfonyl amide; p-Aminobenzenesulfonamide; p-Anilinesulfonamide; Sulfanilamide | 63-74-1 | C6H8N2O2S | 详情 | 详情 |