Shan Li-Hong, Liu Hong-Min, Huang Ke-Xue, Dai Gui-Fu, Cao Chen, Dong Rui-Jing
New Drug Research and Development Center of Zhengzhou University, Zhengzhou 450001, China.
Bioorg Med Chem Lett. 2009 Dec 1;19(23):6637-9. doi: 10.1016/j.bmcl.2009.10.019. Epub 2009 Oct 14.
A series of novel 3beta, 7alpha, 11alpha-trihydroxy-pregn-21-benzylidene-5-en-20-one derivatives were synthesized and characterized by NMR, HRMS. The pregnenolone (1) was first biotransformed by Mucor circinelloides var lusitanicus to 3beta, 7alpha, 11alpha-trihydroxy-pregn-5-en-20-one (3), then 3 was treated with various benzaldehydes to produce 3beta, 7alpha, 11alpha-trihydroxy-pregn-21-benzylidene-5-en-20-one derivatives. These derivatives showed remarkable activity against EC109 cells. The absolute configuration of 3 was also confirmed by signal-crystal X-ray analysis.
合成了一系列新型的3β,7α,11α-三羟基-孕甾-21-亚苄基-5-烯-20-酮衍生物，并通过核磁共振（NMR）、高分辨质谱（HRMS）对其进行了表征。孕烯醇酮（1）首先被葡萄牙圆酵母转化为3β,7α,11α-三羟基-孕甾-5-烯-20-酮（3），然后用各种苯甲醛处理3以制备3β,7α,11α-三羟基-孕甾-21-亚苄基-5-烯-20-酮衍生物。这些衍生物对EC109细胞显示出显著活性。3的绝对构型也通过单晶X射线分析得以确证。
