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【结 构 式】 
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【药物名称】Sulofenur, LY-186641 【化学名称】N-(4-Chlorophenylaminocarbonyl)indane-5-sulfonamide 【CA登记号】110311-27-8 【 分 子 式 】C16H15ClN2O3S 【 分 子 量 】350.82655 |
【开发单位】Lilly (Originator) 【药理作用】ONCOLYTIC DRUGS |
合成路线1
1) 5-Indansulfonamide (I) is converted to ethyl N-(5-indansulfonyl)carbamate (II) with ethyl chloroformate and potassium carbonate in refluxing 2-butanone, which is then reacted with 4-chloroaniline (III) in toluene at reflux to provide sulofenur. 2) Alternatively, (I) can be converted to its anion with NaOH in aqueous acetone, then reacted with 4-chlorophenylisocyanate (IV) to give sulofenur directly.
| 【1】 Grindey, G.B.; Indentification of diarylsulfonylureas as novel anticancer drugs. Proc Amer Assoc Cancer Res 1988, 29, 553-6. |
| 【2】 Grossman, C.S.; Kramer, K.E.; Crowell, T.A.; Grindey, G.B.; Rieder, B.J.; Rinzel, S.M.; Harper, R.W.; Howbert, J.J.; Tao, E.V.; Aikins, J.; Shaw, W.N.; Poore, G.A.; Todd, G.C.; Novel agents effective against solid tumors: The diarylsulfonylureas. Synthesis, activities and analysis of quantitative structure-activity relationships. J Med Chem 1990, 33, 9, 2393-407. |
| 【3】 Howbert, J.J.; Sulofenur. Drugs Fut 1991, 16, 6, 517. |
| 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) | 12032 | 5-Indanesulfonamide | 35203-93-1 | C9H11NO2S | 详情 | 详情 |
| (II) | 12033 | ethyl N-(2,3-dihydro-1H-inden-5-ylsulfonyl)carbamate | C12H15NO4S | 详情 | 详情 | |
| (III) | 12034 | 4-Chlorophenylamine; 4-Chloroaniline; p-Chloroaniline | 106-47-8 | C6H6ClN | 详情 | 详情 |
| (IV) | 12035 | 4-chlorophenyl isocyanate; 1-Chloro-4-isocyanatobenzene; p-Chlorophenyl isocyanate | 104-12-1 | C7H4ClNO | 详情 | 详情 |
Extended Information