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作 者:袁虎 叶霁[2] 陈浩[2] 赵增[2] 李玉柱 张卫东[1,2] 孙青龑
机构地区:[1]中国医药工业研究总院,上海200040 [2]第二军医大学药学院,上海200433
出 处:《有机化学》2016年第12期2960-2964,共5页Chinese Journal of Organic Chemistry
基 金:长江学者奖励计划;国家自然科学基金(Nos.81520108030;81573318;81373301;1302658);上海市重点学科建设(No.B906);上海活性天然产物制备工程研究中心(No.10DZ2251300)资助项目~~
摘 要:汉黄芩素(wogonin,5,7-二羟基-8-甲氧基黄酮)是传统中草药黄芩的有效成分之一,其抗肿瘤活性显著,且对肿瘤细胞的杀伤作用有其独特的机制.目前报道的化学合成法大多总收率较低,反应条件苛刻或原料来源困难.笔者以2,4-二苄氧基-6-羟基苯乙酮与苯甲醛为原料,经Claisen-Schmidt缩合、氧化关环得到5,7-二苄氧基黄酮,通过对5,7-二苄氧基黄酮的8-位碘代、硼酸酯化和氧化从而高效引入8-位羟基,再经甲基化和脱苄基保护完成汉黄芩素的克级合成,总收率大于70%,且反应条件温和、无需柱层析,适合规模化生产.为该类化合物的进一步结构修饰、活性和机制研究提供了保障.Wogonin (5,7-dihydroxy-8-methoxyflavone) is an active component isolated from the Traditional Chinese Medicine (TCM) Huang Qin, which exhibits significant anti-tumor activity via a unique mechanism. The reported chemical synthesis of wogonin suffered either from low overall yield, harsh reaction conditions or from noncommercially available starting materials. In this paper, a new synthesis of wogonin was achieved via Claisen-Schmidt condensation, cyclization, iodination at C-8 position of flavone, borylation of sterically hindered aryl iodides, oxidation of boronic esters, methylation and debenzylation reaction using 2,4-dibenzyloxy-6-hydroxy phenylacetone and benzaldehyde as the starting materials, which provided gram-scale wogonin in 〉70% overall yield. The total synthesis employs mild reaction conditions and conventional flash column chromatography is not needed for purification, which makes it suitable for large-scale production. The efficient and flexible entry should offer opportunities for further modification and chemical biology investigations.
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