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.
出处
《合成化学》
CAS
CSCD
北大核心
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]
关键词
苯并吡喃黄酮
3-烃基黄酮
合成
抗肿瘤活性
benzopyranylflavonoid
3-alkyl flovonoid
synthesis
anti-tumor activity
