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【结 构 式】 
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【药物名称】G-20000, L-39 【化学名称】17-(5-Isoxazolyl)androsta-4,16-dien-3-one 【CA登记号】196711-63-4 【 分 子 式 】C22H27NO2 【 分 子 量 】337.46599 |
【开发单位】University of Maryland (Originator), Genta (Licensee) 【药理作用】Oncolytic Drugs, Prostate Cancer Therapy, 17alpha-Hydroxylase/C17-20 Lyase Inhibitors, Androgen Receptor Antagonists, Steroid 5alpha-Reductase Inhibitors |
合成路线1
Claisen condensation of 3-beta-acetyloxypregna-5,16-dien-20-one (I) with ethyl formate in the presence of NaOMe in pyridine, with simultaneous deacetylation, provided the corresponding 21-formyl derivative (II). Subsequent treatment of (II) with hydroxylamine yielded isoxazole (III) as the only regioisomer. Finally, Oppenauer oxidation of (III) with cyclohexanone and aluminum isopropoxide gave rise to the target alpha,beta-unsaturated ketone.
| 【1】 Ling, Y.; et al.; 17-Imidazolyl, pyrazolyl, and isoxazolyl androstene derivatives, novel steroidal inhibitors of human cytochrome C17,20-lyase (P45017alpha). J Med Chem 1997, 40, 20, 3297. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 16602 | ethyl formate | 109-94-4 | C3H6O2 | 详情 | 详情 | |
| (I) | 32586 | (3S,8R,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | 979-02-2 | C23H32O3 | 详情 | 详情 |
| (II) | 32587 | (Z)-3-hydroxy-1-[(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-propen-1-one | C22H30O3 | 详情 | 详情 | |
| (III) | 32588 | (3S,8R,9S,10R,13S,14S)-17-(5-isoxazolyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol | C22H29NO2 | 详情 | 详情 |