四元环丁烷的合成及其生物活性  

Synthesis and Biological Properties of Quaternary Cyclobutane

作　　者：纪周群[1] 杨婷 顾婷婷 苏景康 唐炜[1] 梁旭 JI Zhouqun;YANG Ting;GU Tingting;SU Jingkang;TANG Wei;LIANG Xu*(The First Clinical Medical College,Affiliated Hospital of Jiangsu University,Zhenjiang 212013,China;School of Chemistry and Chemical Engineering,Jiangsu University,Zhenjiang 212013,China)

机构地区：[1]江苏大学附属医院,江苏大学第一临床医学院,江苏镇江212013 [2]江苏大学化学化工学院,江苏镇江212013

出　　处：《合成化学》2024年第8期723-730,共8页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21701058)。

摘　　要：光照下[2+2]环加成反应能高效合成复杂化合物,是获得季环化合物最直接、有效的方法之一。本文成功合成1例丙烯腈化合物2及其[2+2]光环化四元环丁烷衍生物3,并对其结构,热稳定性与生物活性进行了研究。结果表明:[2+2]光环化反应降低了分子共轭性;化合物2和化合物3热稳定性良好,常温下呈晶态;化合物2和3与小牛胸腺ct DNA的荧光猝灭机制均为单一猝灭,且光环化四元环丁烷衍生物3对口腔鳞状癌细胞(OSCC)有抑制作用,半抑制浓度(IC_(50))为1.944 mol·L^(-1)。The[2+2]cycloaddition reaction under light irradiation can efficiently synthesize complex compounds,which is one of the most direct and effective methods to obtain quaternary compounds.Herein,we successfully synthesized a acrylonitrile compound 2 and its[2+2]cyclized quaternary cyclobutane derivative 3,and also studied their structures,thermal stabilities,and biological activities.The results indicate that[2+2]cyclization reaction reduces molecular conjugation.Compounds 2 and 3 have the satisfied thermal stabilities and are in a crystalline state at room temperature.The fluorescence quenching mechanism of compounds 2 and 3 and calf thymus ct DNA is single quenching,and the cyclized quaternary cyclobutane derivative 3 has an inhibitory effect on oral squamous cell carcinoma cells(OSCC),with a half inhibitory concentration(IC_(50))of 1.944 mol·L^(-1).

关 键 词：环丁烷 晶体结构 电子结构 ct DNA相互作用 口腔鳞状癌细胞抑制 

分 类 号：O622.1[理学—有机化学]