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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 one of the active ingredients of Scutellaria baicalensis Georgi. Its anti-tumor activity is significant and its killing effect on tumor cells has its own unique mechanism. Most of the reported chemical synthesis methods have lower overall yield, harsh reaction conditions or difficult sources of raw materials.In this paper, 2,4-dibenzyloxy-6-hydroxyacetophenone and benzaldehyde were used as raw materials to make Claisen-Schmidt condensation and oxidation The 5,7-dibenzyloxy flavone is removed by ring closure and the 8-position hydroxyl group is efficiently introduced by 8-position iodination, boronic acid esterification and oxidation of 5,7-dibenzyloxyflavone followed by methylation And debenzylic protection, the total yield of Wogonin is more than 70%, and the reaction conditions are mild, without column chromatography, suitable for large-scale production.For the further structural modification, activity and mechanism of these compounds The protection.