基于姜黄酮骨架的新型螺环氧化吲哚类化合物的合成及其抗癌活性  

Synthesis and Anticancer Activities of Novel Turmerone-spiropyrrolidinyloxindoles

作　　者：姚一鸣 杨超[1] 陈爽[1] 左雄 刘雄利[1] 余章彪[1] YAO Yi-ming;YANG Chao;CHEN Shuang;ZUO Xiong;LIU Xiong-li;YU Zhang-biao(Guizhou Medicine Edicine Edible Plant Resources Research and Developmant Center,Guizhou University,Guiyang 550025,China)

机构地区：[1]贵州大学贵州省药食同源植物资源开发工程技术研究中心,贵州贵阳550025

出　　处：《合成化学》2019年第1期40-43,共4页Chinese Journal of Synthetic Chemistry

基　　金：贵州省科技计划项目(黔科合基础[2017]1035);贵州大学教育教学改革研究项目(校教发[2015]64)

摘　　要：以取代靛红、芳姜二烯酮与α-氨基苯乙酸为原料,在甲苯中回流,经1,3-偶极子3+2环加成反应合成了3个新型的基于姜黄酮骨架螺环氧化吲哚类化合物(3a～3c),收率65%～73%,dr值10/1～15/1,其结构经~1H NMR,^(13)C NMR和HR-MS(ESI-TOF)表征,相对构型经3c的单晶结构确定。采用MTT法研究了3a～3c对人白血病细胞(K562)、人肺癌细胞(A549)和人前列腺癌(PC-3)的体外抗肿瘤活性。结果表明:化合物3b对K562具有明显的抑制活性(IC_(50)为37. 5μM),接近于阳性对照药顺铂。Three novel turmerone-spiropyrrolidinyloxindoles(3a^3c)were synthesized via a multicomponent 1,3-dipolar cycloaddition event of dienones with azomethine ylides(thermally generated in situ from isatins and alpha-aminophenylacetic acid).The yields and dr were 65%~73%and 10/1~15/1,respectively.The structures were characterized by 1H NMR,13C NMR and HR-MS(ESI-TOF).The relative configuration were further confirmed by X-ray crystallographic studies of single crystal of 3c.The in vitro antitumor activities against human leukemia cells(K562),human lung cancer cell(A549)and human prostate cancer(PC-3)were demonstrated by MTT assays.The results showed that 3b exhibited well inhibition activities against K562 with IC50 37.5μM,and showed equipotent potent than the positive control of Cisplatin.

关 键 词：靛红 芳姜二烯酮 α-氨基苯乙酸 姜黄酮骨架螺环氧化吲哚类化合物 环加成反应 合成 抗肿瘤活性 

分 类 号：O626.13[理学—有机化学] O623.7[理学—化学]