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

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。

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

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'-bromomethylbiphenyl-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.