消旋藁本酚及其类似物的合成研究

STUDIES ON THE SYNTHESIS OF dl-LIGUSTIPHENOL AND ITS ANALOGUES

摘要: 藁本酚是从中药藁本根茎中分离到的新的倍半萜类化合物,有较强的免疫抑制、抗炎活性。为了进一步研究该化合物的药理活性,对其进行了合成研究。以异丁醛、间甲酚为起始原料,经溴取代、芳烃碘代、羟基保护、格氏反应、Aldol缩合反应,脱保护等6步反应完成了消旋藁本酚的全合成。经¹H-NMR,MS,IR分析,并与天然产物藁本酚比较,目的物得到证实。为了研究藁本酚的构效关系,设计并合成了5个类似物。初步的药理研究没有发现相应的生理活性。

Abstract: S-(-)-Ligustiphenol is a new sesquiterpene with antiinflammatory and immunosuppressive activities. In order to study its pharmacological activities, the total synthesis of its racemat was carried out by a six-step reaction sequence including bromination of aldehyde, iodination of m-cresol, protection of phenolic hydroxyl, Grignard reaction, Aldol condensation, etc.The target compound was characterized by comparing its ¹HNMR, MS and IR spectra with natural (-)-ligustiphenol. In order to study the structureactivity relationships of ligustiphenol, its five analogues were designed and synthesized. The pharmacological screening of these analogues has been performed.