3-芳基香豆素衍生物的合成及其生物活性研究  

Synthesis and Biological Activities of 3-Aryl Coumarin Derivatives

作　　者：成昭[1,2] 梁玲玲 苗延青[1,2] CHENG Zhao;LIANG Ling-ling;MIAO Yan-qing(School of Pharmaceutical Sciences,Xi’an Medical University,Xi’an 710021,China;Institute of Medicine,Xi’an Medical University,Xi’an 710021,China)

机构地区：[1]西安医学院药学院,陕西西安710021 [2]西安医学院药物化学研究所,陕西西安710021

出　　处：《合成化学》2019年第7期554-558,共5页Chinese Journal of Synthetic Chemistry

基　　金：陕西省科技厅自然科学项目(2019JQ-068);陕西省教育厅自然科学项目(18JK0664);西安医学院科研项目(2017GJFY04)

摘　　要：对3-芳基香豆素母核进行修饰,以芳基乙酸和水杨醛为起始原料,三乙胺为催化剂,乙酸酐为溶剂,经缩合反应分别引入吸电子基团三氟甲基和给电子基甲氧基,合成了3-(4′-三氟甲基苯基)香豆素(2a)和新化合物3-(4′-甲氧基苯基)香豆素(2b),其结构经UV-Vis、1HNMR、IR和MS表征。并对其生物活性和荧光标记特性进行了研究。结果表明:2a和2b显示较强的细胞增殖抑制活性、抑菌活性,浓度为4000μmol·L^-1时,对ECV304细胞的抑制率分别为84.22%和65.56%,对大肠杆菌、绿脓杆菌和金黄色葡萄球菌均显示抑菌活性,具有较好的荧光特性,可用于细胞染色及荧光标记。Through modification of phenyl substitution at C-3 in the coumarin moiety, 3-(4′-trifluoromethylphenyl)coumarin( 2a ) and an unreported compound 3-(4′-methoxylphenyl)coumarin( 2b ) were synthesized by condensation reaction under the catalysis of triethylamine using aryl acetic acid and salicylaldehyde as initial reagents. The structures were characterized by UV-Vis, IR, 1 H NMR and MS. The biological properties and fluorescent labelling were analyzed. It was indicated that 2a and 2b demonstrated good cytotoxicity to ECV304, Hela and A549 in vitro , the cytotoxicity towards ECV304 were 84.22% and 65.56%, respectively, at the concentration of 4000 μmol·L -1 . Moreover, Bauer analysis showed the good bacteria inhibition activities of 2a / 2b towards Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus. Further fluorescence analyses indicated their steady fluorescent characteristics, which could be used in fluorescence labelling and imaging.

关 键 词：芳基乙酸 水杨醛 3-芳基香豆素 合成 细胞毒性 抑菌活性 荧光成像 

分 类 号：O621.2[理学—有机化学]