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【结 构 式】 
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【药物名称】 【化学名称】Sulfamic acid 17alpha-(4-tert-butylbenzyl)-17-hydroxyestra-1,3,5(10)-trien-3-yl ester 【CA登记号】 【 分 子 式 】C29H39NO4S 【 分 子 量 】497.70248 |
【开发单位】Université Laval (Originator) 【药理作用】Oncolytic Drugs, Steryl Sulfatase Inhibitors |
合成路线1
Grignard reagent (II), prepared from 4-tert-butylbenzyl bromide (I) and magnesium in Et2O, was condensed with estrone (III) to provide the 17-(tert-butylbenzyl)estradiol (IV). Subsequent reaction of (IV) with sulfamoyl chloride in the presence of 2,6-di-tert-butyl-4-methylpyridine (DBMP) yielded the title sulfamate ester.
| 【1】 Labrie, F.; Boivin, R.P.; Luu-The, V.; Ciobanu, L.C.; Poirier, D.; Potent inhibition of steroid sulfatase activity by 3-O-sulfamate 17alpha-Benzyl(or 4'-tert-butylbenzyl)estra-1,3,5(10)-trienes: Combination of two substituents at positions C3 and c17alpha of estradiol. J Med Chem 1999, 42, 12, 2280. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 40598 | amidosulfonoyl chloride | 7778-42-9 | H2ClNO2S | 详情 | 详情 | |
| (I) | 20588 | 1-(bromomethyl)-4-(tert-butyl)benzene | 18880-00-7 | C11H15Br | 详情 | 详情 |
| (II) | 34441 | bromo[4-(tert-butyl)benzyl]magnesium | C11H15BrMg | 详情 | 详情 | |
| (III) | 20468 | (8R,9S,13S,14S)-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one | 53-16-7 | C18H22O2 | 详情 | 详情 |
| (IV) | 34442 | (8R,9S,13S,14S,17R)-17-[4-(tert-butyl)benzyl]-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol | C29H38O2 | 详情 | 详情 |
Extended Information