| 非那甾胺的合成 |
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| 引用本文： | 李效军,方芳,王晓季,陈立功.非那甾胺的合成[J].天津大学学报(英文版),2001,7(4):286-289. |
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| 作者姓名： | 李效军 方芳 王晓季 陈立功 |
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| 作者单位： | 天津大学药物科学与技术学院, |
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| 摘 要： | 非那甾胺是一种底物竞争型 5 α-还原酶抑制剂 ,用于良性前列腺增生的临床治疗 .本文提出了一种新的合成方法 ,以孕烯醇酮为原料经 10步反应制得了非那甾胺 ,即季铵化、甲氧基化、Oppenauer氧化、水解、氧化切断 Δ4-双键、氨解环合、Δ5-双键加氢、酯化、A环 1,2位脱氢和 Bodroux反应 .本方法避免了文献中昂贵试剂 2 ,2 -二硫吡啶的使用 .经质谱和 /或核磁共振确定了所有化合物结构 .以孕烯醇酮计 ,非那甾胺的总收率为 13.6 7% .
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| 关 键 词： | 非那甾胺 全合成 孕烯醇酮 |
SYNTHESIS OF FINASTERIDE |
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| LI Xiao-jun,FANG Fang,WANG Xiao-Ji,CHEN Li-gong.SYNTHESIS OF FINASTERIDE[J].Transactions of Tianjin University,2001,7(4):286-289. |
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| Authors: | LI Xiao-jun FANG Fang WANG Xiao-Ji CHEN Li-gong |
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| Abstract: | As a kind of substrate competition-type 5α-reductase inhibitor,finasteride is a promising medicine used in the clinical treatment of benign prostatic hyperplasia (BPH).In this paper,a new route for the synthesis of finasteride from pregnenolone was proposed.Thus,pregnenolone was converted to finasteride in 10 steps,i.e.,ammoniumation,methoxylation,Oppenauer xidation,hydrolyzation,cleavage of Δ4-double bond by oxidation,ring closure by ammonia,hydrogenation of Δ5-double bond,esterification with methanol,dehydrogenation of 1,2-position in A-ring and Bodroux reaction.In this route,expensive reagent 2,2-dipyridyl-disulfide commonly used in previous literature was avoided.All of the desired compounds were characterized by MS or/and NMR.The overall yield of finasteride was 13.67% based on pregnenolone. |
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| Keywords: | finasteride synthesis pregnenolone |
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