缩氨基硫脲类化合物的设计合成与生物活性研究.pdfVIP

2006 年第26 卷 有 机 化 学 Vol. 26, 2006 第4 期, 528～532 Chinese Journal of Organic Chemistry No. 4, 528～532 ·研究简报· 缩氨基硫脲类化合物的设计合成和生物活性研究 李清寒 陈淑华* ( 四川大学化学学院 成都 610064) 摘要 通过 CS , H NNH •H O, (CH O) SO 反应制得肼基二硫代甲酸甲酯, 肼基二硫代甲酸甲酯再与相应的醛或酮, 2 2 2 2 3 2 4 通过缩合反应制得中间体化合物1a～1h, 产率78%～96%. 以乙醇作溶剂, 1 与吗啉、哌嗪、N-单取代哌嗪发生取代反 应制得相应的目标化合物2, 3, 4, 产率57%～84%. 共计合成目标化合物16 个, 均为新化合物, 并且有2 个中间体为新 化合物. 以上新化合物均经熔点、质谱、元素分析、红外光谱、核磁共振氢谱确证. 通过对目标化合物进行体外抗菌、 抗癌活性测试表明, 16 个目标化合物中, 化合物3f 具有较强的抑菌活性, 化合物4c 具有一定的抗癌作用. 关键词 缩氨基硫脲; 合成; 抗癌活性; 抗菌活性 Studies on Synthesis and Bioactivity of Thiosemicarbozones LI, Qing-Han CHEN, Shu-Hua* (College of Chemistry, Sichuan University, Chengdu 610064) Abstract Sixteen thiosemicarbazones 2～4 were synthesized from following three steps: firstly hydrazine reacted with carbon disulfide and dimethyl sulfate to form methyl hydrazino-dithiocarboxylate with yield of 60%, which further reacted with ketone or aldehyde in i-PrOH to give 1a～1h with yields of 78%～96%. Treatment of compound 1 with piperazine, N-substituted piperazine or morpholine in ethanol afforded 2～4 1 in 57%～84% yields. All compounds were characterized by elemental analysis, MS, IR and H NMR spec- tra. The antibacterial and anticancer activities in vitro of all compounds have been determined. The results show that compound 3f possesses strong antibacterial activity while the compound 4c possesses anticancer ac- tivity. Keywords thiosem