摘要
以对羟基苯甲醛和2,4-二羟基苯乙酮为起始原料,经过甲氧甲基化、溴代、Ullmann反应、羟醛缩合和脱保护等反应,完成了天然产物双查尔酮Luxenchalcone的全合成,关键步骤为Ullmann反应,重要中间体和目标产物的化学结构经1H NMR,13C NMR和ESI-MS等表征确认.
Luxenchalcone was first isolated from the leaves of Luxemburgia octandra in 2004 by Brazil chemists.In 2007 this compound was proved to have significant cytotoxicity on HT-29 colon adenocarcinoma,NC1-H460 non-small cell lung carcinoma,MCF-7 breast cancer cell,OVCAR-3 ovarian adenocarcinoma cells and RXF-393 renal cell carcinoma.But the natural compound has not been synthesized in the literature.In order to synthesize Luxenchalcone,based on the natural product symmetry,the key step was Ullmann reac-tion,and then the natural product was easily to obtain by aldo condensation.In this work,Luxenchalcone was synthesized by methoxymethylation,bromination,Ullamnn reaction,aldo condenstion,deprotective group from 2,4-bihydroxyacetophone and 4-hydroxybenzaldehyde in 18%overyield.The structure of Luxenchalcone and intermediates were confirmed by 1H NMR,13 C NMR and ESI-MS.The synthesis of this compound maybe gives some vital significance to find lead compounds.
出处
《高等学校化学学报》
SCIE
EI
CAS
CSCD
北大核心
2013年第12期2734-2737,共4页
Chemical Journal of Chinese Universities
基金
甘肃省自然科学基金(批准号:3ZS062-B25-017)资助
作者简介
联系人:张应鹏,男,博士,副教授,主要从事生物有机化学研究.E-mail:yingpengzhang@126.com
