氧甲氢龙衍生物的合成  

Synthesis of oxandrolone derivatives

作　　者：赵滟萍[1] 黎万[1] 吕露[1] 屈洁[1] 常永志[2] 丁聪[1] 李宗桃[1] 

机构地区：[1]武汉大学药学院,湖北武汉430072 [2]新疆农业大学食品科学与药学学院,新疆乌鲁木齐830052

出　　处：《中国药物化学杂志》2010年第6期501-507,共7页Chinese Journal of Medicinal Chemistry

摘　　要：目的设计合成氧甲氢龙的衍生物。方法以3β-羟基-5α-雄甾烷-17-酮为原料经氧化开环、还原、缩合得到中间体17β-羟基-A-失碳-5α-雄甾烷-2-酮,此中间体与不同的酰氯反应生成的一系列C17位酰化产物再经过Baeyer-Villiger反应得到氧甲氢龙衍生物系列A;以3β-羟基-5α-雄甾烷-17-酮为原料与不同酰氯反应生成氧甲氢龙衍生物系列B;以3β-羟基-5α-雄甾烷-17-酮的酰化产物为原料经过Baeyer-Villiger反应得到氧甲氢龙衍生物系列C。结果与结论合成了3个系列22个未见报道的新化合物,目标化合物的结构均经1H-NMR、IR、MS谱确证。Aim To design and synthesize novel oxandrolone derivatives.Methods Intermediate 17β-hydroxy-A-nor-5α-androstan-2-one synthesized from 3β-hydroxy-5α-androstan-17-one by oxidation,reduction and Dieckmann condensation was reacted with eight different acyl chlorides and followed by Baeyer-Villiger oxidation to form oxandrolone derivatives series A;oxandrolone derivatives series B were obtained from 3β-hydroxy-5α-androstan-17-one by acylation with ten different acyl chlorides;oxandrolone derivatives series C were synthesized from 3β-acyl chloride-5α-androstan-17-one derivatives by Baeyer-Villiger oxidation.Results and conclusion Twenty-two novel compounds（A1-C4） were synthesized successfully.The structure of target compounds were identified by IR,1H-NMR and MS.

关 键 词：化学合成 氧甲氢龙 衍生物 酰化反应 BAEYER-VILLIGER氧化 

分 类 号：R914[医药卫生—药物化学]