3β-乙酰氧基-17a-氮杂-D-homo-5(6)-雄甾烯-17-酮的化学合成与生物转化

Chemical synthesis and biotransformation of 3β-acetoxy-17a-aza-D-homo-5(6)-androst-17-one

目的:设计并合成具有潜在生物活性的氮杂甾体衍生物。方法:对文献合成方法进行了适当改进,以去氢表雄酮为起始原料,经过酰化、肟化、重排三步得到17a氮杂雄甾衍生物,将其用本实验室自筛的菌种Mucor circinelloides lusitanicus进行生物转化。结果与结论:以78%的收率得到17a氮杂雄甾衍生物,转化结果表明菌种Mucor circinelloides lusitanicus能够水解17a氮杂雄甾3位的酯键,同时产生其7α羟基化衍生物。化合物的结构经IR(红外光谱)、NMR(核磁共振光谱)及MS(质谱)等方法确证。

Aim： To design and synthesize new azasteroids with potential bioactivities. Methods：Dehydroepiandrosterone was transformed to its 17a-aza derivative through 3 reaction steps including acetylation, oximation and Beckmann rearrangement. The 17a-aza derivative was then transformed by fimgus of Mucor circinelloides lusitanicus. Results and conclusion ：17a-aza derivative of dehydroepiandrosterone was obtained with 78% yield by improving the synthesis method. The fimgus could transform this kind of compound by hydrolyzing the ester and 7α-hydroxylation. All of the compounds were identified by IR, NMR and MS spectrum.