含哌嗪片段的噻吩查尔酮衍生物的合成及其抗菌活性  

Synthesis and Antibacterial Activity of Thienyl Chalcone Derivatives Bearing Piperazine Moiety

作　　者：黎勇坤 唐燕玲 李敏欣 杨小碧 高慧 毛泽伟 Li Yongkun;Tang Yanling;Li Minxin;Yang Xiaobi;Gao Hui;Mao Zewei(College of Pharmaceutical Science,Yunnan University of Chinese Medicine,Kunming 650500)

机构地区：[1]云南中医药大学中药学院,昆明650500

出　　处：《有机化学》2020年第1期108-114,共7页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.81560620);云南省科学技术厅-云南中医药大学应用基础研究联合专项(No.2017FF117(-023))资助项目。

摘　　要：查尔酮是一类具有多种生物活性的1,3-二苯基丙烯酮化合物.以4-氟苯乙酮和2-噻吩甲醛为原料出发,经取代、Aldol反应和衍生化,合成得到16个未见文献报道的含哌嗪片段的噻吩查尔酮衍生物.以氧氟沙星、左氧氟沙星、莫西沙星作阳性对照,采用K-B纸片扩散法测试了目标化合物对金黄色葡萄球菌(Staphylococcus aureus Rosenbach)、大肠埃希菌(Escherichia coli)和枯草芽孢杆菌(Bacillus subtilis)的抑菌活性.结果表明,(E)-1-[4-(4-肉桂酸甲酯甲基哌嗪基)苯基]-3-(噻吩-2-基)丙-2-烯酮(4b)和(E)-1-{4-[4-(2-氧亚基苯乙基)哌嗪基]苯基}-3-(噻吩-2-基)丙-2-烯酮(4e)对枯草芽孢杆菌高度敏感,且最低抑菌浓度为4.0μg/m L.Chalcone derivatives are a kind of 1,3-diphenylacrylketone compounds with a broad range of biological activities. A series of new thienyl chalcone derivatives bearing piperazine moiety have been designed and prepared based on the principle of bioisosteres and molecular hybridization. Their antibacterial activities against Staphylococcus aureus Rosenbach, Escherichia coli and Bacillus subtilis were evaluated. The results showed that thienyl chalcone derivatives exhibited good selective inhibitory activities against the three tested strains, respectively. Especially,(E)-1-[4-(4-methylcinnamatemethylpiperazinyl)-phenyl]-3-(thien-2-yl)propyl-2-ketene(4 b) and(E)-1-{4-[4-(2-oxophenethyl)piperazinyl]phenyl}-3-(thien-2-yl)propyl-2-ketene(4 e) were found to be very sensitive to Bacillus subtilis, and the minimum inhibitory concentration(MIC) is 4.0 μg/m L against Bacillus subtilis.

关 键 词：噻吩 查尔酮 抗菌活性 最低抑菌浓度 

分 类 号：O626[理学—有机化学] TQ465[理学—化学]