摘要
2′,4′-二羟基-3″-（2″-羟基-3″-甲基-3″-丁烯基）查尔酮Sanjuanolide是从Dalea frutescens（当地人称为达列亚草原草）中提取出来的,该天然产物对前列腺癌细胞具有明显的抗增殖活性。以廉价的2,4-二羟基苯乙酮、苯甲醛等为原料,以总收率4.8%完成了Sanjuanolide的首次全合成,并经过路线优化将总收率提高至15.3%,有效提高了合成效率,可用于Sanjuanolide的较大量合成。合成过程中的关键步骤是利用光氧化法将取代的异戊烯基侧链变成2″-羟基-3″-甲基-3″-丁烯基侧链。所有新化合物的结构都经NMR、HR-MS、IR确认。
2′,4′-Dihydroxy-3′-（ 2″-methyl-3″-hydroxy-1″-butanyl） chalcone sanjuanolide was isolated from Dalea frutescens. The compound has obvious antiproliferative activity to prostate cancer cells. Chalcone sanjuanolide was first total synthesized from cheap starting material 2,4-didroxyacetophenone and benzaldehyde and the total yield was 4. 8%. Then the total yield was increased to 15. 3% by route optimization.Greatly improved the efficiency of synthesis.The key step of synthesis is to change the side chain of isopentenyl to 2″-methyl-3″-hydroxy-1″-butanyl by photo oxidation.The structures of all new compounds were confirmed by NMR,IR and HR-MS.
作者
李方辉
杨金会
牛明杰
马涛
冯月基
严志明
LI Fang-hui;YANG Jin-hui;NIU Ming-jie;MA Tao;FENG Yue-ji;YAN Zhi-ming(College of Chemistry and Chemical Engineering,State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering,Ningxia University,Yinchuan 750021,China)
出处
《化学试剂》
CAS
北大核心
2018年第8期789-793,800,共6页
Chemical Reagents
基金
国家自然科学基金资助项目(21362025)
关键词
光氧化
查尔酮
全合成
抗癌
photo oxidation
chalcone
total synthetic
antibacteria
