含1-[4-二-(4-氟苯)甲基]哌嗪官能团的硫代酰胺的合成及生物活性  

Synthesis and biological activities of thioamides bearing[1-bi-(4-fluorophenyl)methyl]-piperazine unit

作　　者：郭少鹏 罗瑞强 张志豪 李清寒[1,2,3] GUO Shao-peng;LUO Rui-qiang;ZHANG Zhi-hao;LI Qing-han(College of Chemistry and Environment,Southwest Minzu University,Chengdu 610041,China;Key Laboratory of General Chemistry of the National Ethnic Affairs Commission,College of Chemistry and Environment,Southwest Minzu University,Chengdu 610041,China;Key Laboratory of pollution Control Chemistry and Environmental Functional materials for Qinghai-Tibet Plateau of the National Ethnic Affairs Commission,College of Chemistry and Environment,Southwest Minzu University,Chengdu 610041,China)

机构地区：[1]西南民族大学化学与环境学院,四川成都610041 [2]西南民族大学化学与环境学院,国家民委基础化学重点实验室,四川成都610041 [3]西南民族大学化学与环境学院,青藏高原污染控制化学与环境功能材料重点实验室,四川成都610041

出　　处：《化学研究与应用》2022年第3期558-568,共11页Chemical Research and Application

基　　金：西南民族大学中央高校基本科研业务费专项基金学生项目(2021NYYXS25)资助;四川省科技厅科技支撑计划项目(2015NZ0033)资助。

摘　　要：以1-[二-(4-氟苯)甲基]哌嗪、端炔及单质硫为原料,应用吡啶为催化剂和溶剂,在80℃反应24h以18~84%的收率制得了17个含有1-[4-二-(4-氟苯)甲基哌嗪官能团的硫代酰胺衍生物3(a~q)。合成的17个目标化合物通过熔点测定和质谱、红外光谱及氢(碳)核磁共振谱分析对其结构进行确证。并进行了体外抗肿瘤及抗菌活性测试,测试结果表明所有化合物对大肠杆菌(E.coli)及金黄色葡萄球菌(S.aureus)的活性具有一定的抑制作用,其MIC可达64ug·mL^(-1),IC_(50)分别为42.74 ug·mL^(-1)和37.81 ug·mL^(-1);经体外抗肿瘤活性测试表明,在40uM的浓度下,化合物3(a~q)对白血病HL-60细胞及肺癌A-549肿瘤细胞的生长无抑制活性。本文合成方法具有反应操作简单和反应条件温和的优点。Seventeen novel thioamides containing[1-bi-(4-fluorophenyl)methyl]-piperazine group were prepared via a three-component reaction involving alkynes,[1-bi-(4-fluorophenyl)methyl]-piperazine and elemental sulfur powder,using a very simple catalytic system composed of pyridine at 80℃for 24h with good yield(18~84%).The advantage was that a transition metal and an external oxidant were not needed.The structures of the new compounds 3(a~q)were characterized by IR,HMRS,^(1)H NMR,and ^(13)C NMR.The bioactive assay for the newly prepared compounds manifested that all compounds thioamides derivatives exhibited certain inhibitory activity against E.coli(MIC 64 ug·mL^(-1),IC_(50) 42.74 ug·mL^(-1))and S.aureus(MIC 64 ug·mL^(-1),IC_(50) 37.81 ug·mL^(-1)).While all thioamides derivatives had no inhibitory activity on Leukemia HL-60 and Lung cancer A-549 cell in 40uM.

关 键 词：1-[二-(4-氟苯)甲基]哌嗪 端炔 单质硫 硫代酰胺 抗菌活性 抗肿瘤活性 

分 类 号：O623.8[理学—有机化学]