新型去氢木香内酯/郁金香素A拼接螺环氧化吲哚的合成及其抗白血病活性
Synthesis and Anti-human Leukemia Cells Activities of Novel Dehydroxylone/Tulipin A-based Spirooxindole Hybrids
任娜 1石庆辉 1姜维艳 2王慧娟 1刘雄利 1邓国栋1
作者信息
- 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
- 2. 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;贵州装备制造职业学院,贵州贵阳 550025
- 折叠
摘要
开发天然产物优势骨架的多样性衍生物库是天然有机化学的一个重要课题.本文以脯氨酸、靛红和去氢木香内酯/郁金香素A为起始原料,通过[3+2]环加成反应,N-氧化反应和分子内1,2-迁移导致的扩环反应,得到8个未见文献报道的新型目标产物去氢木香内酯/郁金香素A拼接螺环氧化吲哚(4a～4h),总产率43％～63％,dr值＞20∶1,其结构经1H NMR,13C NMR和HR-MS(ESI-TOF)表征,化合物4e的相对构型通过单晶X-射线衍射进一步进行了确定.采用MTT法研究了(4a～4h)对人白血病细胞(K562)的体外抗肿瘤活性.结果表明:去氢木香内酯拼接螺环氧化吲哚(4b,4c)和郁金香素A拼接螺环氧化吲哚(4f,4g)对K562具有一定的抑制活性.
Abstract
Developing a diverse derivative library of privileged natural product frameworks is an impor-tant topic in natural organic chemistry.In this paper,we uses proline,isatins and dehydroxylone/tu-lipin A as starting materials,the reaction undergoes a[3+2]cycloaddition reaction and then N-oxida-tion reaction,intramolecular 1,2-migration-triggered ring expansion reaction to provide 8 dehydroxy-lone/tulipalin A-based spirooxindole hybrids(4a～4h)in 43％～63％overall yields and up to dr＞20∶1.The structures of products 4 were characterized by 1H NMR,13 C NMR and HR-MS(ESI-TOF).The relative configuration of compound 4e was further determined by single crystal X-ray dif-fraction.The in vitro antitumor activities against human leukemia cells(K562)were demonstrated by MTT assays using the commercially available broad-spectrum anticancer drug Cisplatin as a positive control.The results showed that dehydroxylone-based spirooxindole hybrids(4b,4c)and tulipin A-based spirooxindole hybrids(4f,4g)showed good cytotoxic effects.
关键词
去氢木香内酯/郁金香素A/螺环氧化吲哚/N-氧化反应/[3+2]环加成反应Key words
dehydroxylone/tulipalin A/spiroxindoles/N-oxidation reaction/[3+2]cycloaddition reaction引用本文复制引用
出版年
2024
NETL
NSTL
维普
万方数据