摘要
以取代靛红酸酐为起始原料,二甲基亚砜(DMSO)为反应溶剂,在三乙烯二胺(DABCO)的作用下加热至80℃,与取代靛红经形式上的(4+2)环化反应以81%~94%的收率合成了一系列色胺酮衍生物。化合物结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI-TOF)表征。该制备方法不仅避免了反应过程中金属的使用,而且后处理简单、无需柱层析,在减小对环境影响的同时提升了合成效率。在此基础上,通过最小抑菌浓度(MIC)试验初步揭示了化合物3g良好的体外抗菌活性(<4μg·mL^(-1))。
Using substituted isatoic anhydrides as starting materials,DMSO as solvent,a series of tryptanthrin derivatives were facilely synthesized at 80℃in the presence of DABCO with 81%to 94%yields via the formal(4+2)annulation with substituted isatins.The obtained compounds were characterized by^(1)H NMR,^(13)C NMR and HR-MS(ESI-TOF).This metal-free and column chromatography free method not only reduces the damage to the environment,but also improves the synthesis efficiency.In addition,preliminary minimal inhibitory concentration(MIC)tests reveal that the compound 3g exhibits promising antibacterial activity(<4μg·mL^(-1)).
作者
陈林
刘万聪
王亚鹏
辛子杰
徐鹏帅
代海渝
邓力超
王启卫
张翔
CHEN Lin;LIU Wancong;WANG Yapeng;XIN Zijie;XU Pengshuai;DAI Haiyu;DENG Lichao;WANG Qiwei;ZHANG Xiang(Chengdu Institute of Organic Chemistry,Chinese Academy of Sciences,Chengdu 610041,China;Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province,Sichuan Industrial Institute of Antibiotics,School of Pharmacy,Chengdu University,Chengdu 610106,China;University of Chinese Academy of Sciences,Beijing 100049,China;School of Science,Xihua University,Chengdu 610039,China)
出处
《合成化学》
CAS
2022年第12期917-924,共8页
Chinese Journal of Synthetic Chemistry
基金
国家自然科学基金资助项目(21871031,22071011)
西华大学人才引进项目(Z202084)。
关键词
环化反应
色胺酮衍生物
无金属催化
无柱层析
抗菌活性
cyclization reaction
tryptanthrin derivative
metal-free catalysis
column chromatography free method
antibacterial activity
