新型郁金香素A-氧化吲哚-色酮拼接化合物的合成及其抗人白血病细胞活性  

Synthesis and Anti-human Leukemia Cells Activities of Novel Tulipin A-oxindole-chromone Hybrids

作　　者：赵婉婷 石庆辉 张敏[1] 刘雄利[1] 彭礼军[1] ZHAO Wanting;SHI Qinghui;ZHANG Min;LIU Xiongli;PENG Lijun(National&Local Joint Engineering Research Center for The Exploition of Homology Resources of Medicine and Food,Guizhou University,Guiyang 550025,China)

机构地区：[1]贵州大学西南药食两用资源开发利用技术国家地方联合工程研究中心,贵州贵阳550025

出　　处：《合成化学》2024年第12期1042-1048,共7页Chinese Journal of Synthetic Chemistry

基　　金：贵州省基础研究项目(黔科合基础-ZK[2022]一般144)。

摘　　要：优势骨架天然产物衍生物库的多样性合成是药物化学领域的重要研究方向。基于新的合成策略,以不同取代基的色原酮-氧化吲哚底物(1)和郁金香素A发生Michael加成反应,合成了7个未见文献报道的郁金香素A-氧化吲哚-色酮拼接化合物(3a~3g),产率75%~80%,dr>20∶1。化合物3的结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI-TOF)表征,化合物3g的相对构型通过单晶X-射线衍射进行了确定。采用MTT法研究了化合物3对人白血病K562细胞的体外抗肿瘤活性。结果表明:化合物3b,3e和3f对人白血病K562细胞具有一定的抑制活性。The diversity synthesis of natural product derivative libraries based on privileged frameworks is an important research direction in the field of pharmaceutical chemistry.In this paper,based on a new synthesis strategy,we use oxindole-chromone substrates 1 with different substituents and tulipin A as starting materials,the reaction undergoes a Michael reaction to provide seven novel tulipin A-based oxindole-chromone hybrids(3a~3g)in 75%~80%yields and dr>20∶1.The structure of product 3 was characterized by ^(1)H NMR,^(13)C NMR and HR-MS(ESI-TOF).The relative configuration of compound 3g was further determined by single crystal X-ray diffraction.The in vitro antitumor activities against human leukemia cells(K562)were demonstrated by MTT.The results showed that compounds 3b,3e and 3f showed good cytotoxic effects.

关 键 词：氧化吲哚 郁金香素A 色酮 MICHAEL加成反应 抗人白血病细胞活性 

分 类 号：O626.13[理学—有机化学] O623.7[理学—化学]