2-(2-甲氧基苯基)-5-[2’-(2H-四唑-5-基)联苯-4-甲硫基]-1,3,4-噻二唑的合成及抑菌活性  

Synthesis and antibacterial activities of 5-[4'-(5-(2-methoxylphenyl)-1,3,4-thiadiazol-2-ylsulfanylmethyl)-biphenyl-2-yl]-tetrazole

作　　者：晁淑军[1] 汪应灵[1] 耿明江[1] 程迪[1] 惠新平[2] 许鹏飞[2] 

机构地区：[1]新乡医学院化学教研室,河南新乡453003 [2]兰州大学功能有机分子化学国家重点实验室,甘肃兰州730000

出　　处：《新乡医学院学报》2006年第6期544-545,共2页Journal of Xinxiang Medical University

基　　金：国家自然科学基金资助项目(编号:20021001);新乡医学院2004年高学历人才科研资助项目(编号:04GXLP03)

摘　　要：目的研究2-(2-甲氧基苯基)-5-[2’-(2H-四唑-5-基)联苯-4-甲硫基]-1,3,4-噻二唑(化合物4)的合成方法及抑菌活性。方法通过2-(2-甲氧基苯基)-5-巯基-1,3,4-噻二唑(化合物1)与2-N-三苯基甲基-5-(4’-溴甲基联苯-2-基)-四唑(化合物2)在碳酸钾/丙酮体系中进行缩和反应,制得化合物3。化合物3在酸性条件下脱保护,制得化合物4。用元素分析和波谱方法确定化合物3和4的结构,用杯盘培养法测化合物4的抑菌活性。结果经检测确定化合物3和4分别为2-(2-甲氧基苯基)-5-[(2’-三苯甲基四唑-5-基)联苯-4-基]甲硫基-1,3,4-噻二唑和2-(2-甲氧基苯基)-5-[2’-(2H-四唑-5-基)联苯-4-甲硫基]-1,3,4-噻二唑。初步抑菌结果表明化合物4对大肠杆菌、链球菌显示了较好的抑菌活性。结论化合物4有望成为含有联苯四唑的新抗菌药物。Objective To research the synthetic method and antibacterial activities 5-[4＇-（5-（2-methoxylphenyl）-1,3, 4-thiadiazol-2-ylsulfanylmethyl）-biphenyl-2-yl]-tetrazole（compound 4）. Methods The new compound 3 was synthesized by the condensation of 2-mercapto-5- （ 2-methoxylphenyl ）-1,3, 4-thiadiazole （ compound 1 ） with 2-trityl-5-（ 4＇ -bromomethyl- biphenyl-2-yl）tetrazole（ compound 2） in acetone in the presence of potassium hydroxide. An attempt to remove the trityl group of compound 3 under acidic conditions gave the new compound 4. The structures of the compounds 3 and 4 were confirmed by elementary analyses and spectroscopic methods. The compound 4 was tested for its antibacterial activities using the cup-plate method. Results The compounds 3 and 4 were identified as 5-[4＇-（5-（2-methoxylphenyl）-1, 3,4-thiadiazol-2-ylsulfanylmethyl）-biphenyl-2-yl]-2-trityl-tetrazole and 5-[4＇-（5-（2-methoxylphenyl）-1, 3,4-thiadiazol-2-ylsulfanylmethyl）-biphenyl-2- yl]-tetrazole. Primary antibacterial activities showed by the compound 4 was quite good in bacteriostatic effects against E. coli, Streptococcus. Conclusion The compound 4 is expected to be a new antibacterial bearing biphenyltetrazole.

关 键 词：合成 抑菌活性 1 3 4-噻二唑 2-(2-甲氧基苯基)-5-[2’-(2H-四氮唑-5-基)联苯基-4-甲硫基]巯基-1 3 4-噻二唑 

分 类 号：O624[理学—有机化学]