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【结 构 式】 
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【药物名称】Abiraterone, CB-7598 【化学名称】17-(3-Pyridyl)androsta-5,16-dien-3beta-ol 【CA登记号】154229-19-3 【 分 子 式 】C24H31NO 【 分 子 量 】349.52077 |
【开发单位】BTG (Originator) 【药理作用】Oncolytic Drugs, Prostate Cancer Therapy, 17alpha-Hydroxylase/C17-20 Lyase Inhibitors, Antiandrogens |
合成路线1
Treatment of dehydroepiandrosterone 3-acetate (I) with triflic anhydride and 2,6-di-tert-butyl-4-methylpyridine provided the desired enol triflate (III) along with some 3,5-diene (II), which were separated by column chromatography. Subsequent coupling of triflate (III) with pyridylborane (IV) using bis(triphenylphosphine)- palladium(II) chloride as the catalyst afforded the (3-pyridyl)androstadiene (V), which after hydrolysis of the acetate ester with NaOH provided the target compound.
| 【1】 Potter, G.A.; et al.; Novel steroidal inhibitors of human cytochrome P450(17alpha) (17alpha-hydroxylase-C17,20-lyase): Potential agents for the treatment of prostatic cancer. J Med Chem 1995, 38, 13, 2463. |
| 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) | 20083 | Prasterone acetate;3b-Hydroxy-5-androstene-17-one acetate；Dehydroisoandrosterone acetate;Dehydroepiandrosterone 3-acetate;Dehydroepiandrosterone acetate;(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | 853-23-6 | C21H30O3 | 详情 | 详情 |
| (II) | 20084 | (8R,9S,10R,13S,14S)-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate | C20H25F3O3S | 详情 | 详情 | |
| (III) | 20085 | (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-[[(trifluoromethyl)sulfonyl]oxy]-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | C22H29F3O5S | 详情 | 详情 | |
| (IV) | 20086 | 3-(diethylboryl)pyridine | C9H14BN | 详情 | 详情 | |
| (V) | 20087 | (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-(3-pyridinyl)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | C26H33NO2 | 详情 | 详情 |