新型苯并吡喃黄酮的合成及其抗肿瘤活性  

Synthesis and Anti-tumor Activities of Novel Benzopyranylflavonoids

作　　者：陈斌[1] 刘雄伟[1] 陈诗尧[1] 郭丰敏[1] 刘雄利[1] 周英[1] 

机构地区：[1]贵州大学生命科学学院贵州省中药民族药创制工程中心,贵州贵阳550025

出　　处：《合成化学》2014年第1期30-33,共4页Chinese Journal of Synthetic Chemistry

基　　金：教育部“新世纪人才支持计划”[教技函(2011)95号];贵州省优秀青年科技人才培养对象专项[黔科合人字2011(34)号];2012年贵阳市大学生创新计划基金;贵州大学引进人才科研项目[贵大人基合字(2013)013号]

摘　　要：2,2-二甲基-8-乙酰基-7-羟基-5-甲氧基色满分别与对甲基苯甲酰氯,间氯苯甲酰氯和间三氟甲基苯甲酰氯经Baker-Venkataraman重排和关环反应合成了3个新型的苯并吡喃黄酮(3a^3c);1-(2″,4″-二甲氧基苯基)-3-(2',2'-二甲基-7'-羟基-5'-甲氧基色满-8')-1,3-二酮(4)分别与烯丙基溴,异戊烯基溴和碘甲烷经取代和关环反应合成了3个新型的3-烃基苯并吡喃黄酮(6a^6c)。3和6的结构经1H NMR,13C NMR和MS表征。采用MTT法和SRB法研究了3和6体外对人白血病细胞(K562)和人肺癌细胞(K549)的抗肿瘤活性。结果表明:2',4'-二甲氧基-2″,2″-二甲基-3″,4″-2H二氢吡喃-3-甲基-5″,6″:5,6-黄酮(6c)显示了较好的抗肿瘤活性。Three novel benzopyranylflavonoids（ 3a ~ 3c） were synthesized by Baker-Venkataraman rearrangement and cyclization of 1-（ 7-hydroxy-5-methoxy-2,2-dimethylchromanan-8-yl） ethanone with 4-methylbenzoyl chloride,3-chlorobenzoyl chloride and 3-（ trifluoromethyl） benzoyl chloride,respectively. Futhermore,three novel 3-alkyl benzopyranylflavonoids（ 6a ~ 6c） were synthesized by substitution and cyclization of 1-（ 2″,4″-methoxyphenyl）-3-（ 7＇-hydroxy-5＇-methoxy-2＇,2＇-dimethylchromanan-8＇-yl） propane-1,3-dione with 3-bromoprop-1-ene,1-bromo-3-methybut-2-ene and iodomethane,respectively. The structures were characterized by1H NMR,13C NMR and MS. The vitro anti-tumor activities of 3 and 6 against K562 and K549 were investigated by MTT method and SRB method. The results showed that 2＇,4＇-dimethoxy-2″,2″-dimethy-3″,4″-2H-pyranyl-3-methyl-5″,6″： 5,6-flavonoid（ 6c） exhibited better anti-tumor activities.

关 键 词：苯并吡喃黄酮 3-烃基黄酮 合成 抗肿瘤活性 

分 类 号：O626[理学—有机化学] O621.3[理学—化学]