吡啶取代基二(4-氨基-1,2,4-三氮唑-3-硫醚)的合成及其抑菌活性

Synthesis and Anti-Bacterial Activities of Pyridine Substituted Bis(4-amino-1,2,4-triazole Thioethers)

摘要: 以2,6-吡啶二甲酸为起始原料，经多步化学反应制备吡啶-2,6-二(4-氨基-1,2,4-三氮唑-3-硫醇)中间体，该中间体与卤代烃进行醚化反应得到2个吡啶-2,6-二(4-氨基-1,2,4-三氮唑-3-硫醚)目标化合物，其结构通过¹H NMR、¹³C NMR、MS、IR、元素分析及单晶X-射线衍射等进行表征，采用96孔板倍比稀释法测定目标化合物对金黄葡萄球菌、白色念珠菌、枯草芽孢杆菌、大肠杆菌的抑制活性。实验结果表明：吡啶-2,6-二(4-氨基-1,2,4-三氮唑-3-硫代苄)为孪晶，两个目标化合物在测试浓度范围内对白色念珠菌和大肠杆菌均具有很好的抑制活性，而对金黄葡萄球菌和枯草芽孢杆菌均无抑菌作用。

Abstract: Two pyridine bis(4-amino-1,2,4-triazole-3-thioethers) were synthesized from the starting mate-rial of pyridine-2,6-dicarboxylic acid through multistep chemical reactions in a simple method from etherification reaction of 4-amino-5-(6-(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)pyridin-2-yl)- 4H-1,2,4-triazole-3-thiol with halohydrocarbon, and characterized by ¹H NMR,¹³C NMR, IR, elemental analysis, and sin-gle-crystal X-ray diffraction. The inhibitory activity, compounds 2a and 2b against Escherichia coli, Candida albican, Staphylococcus aureus and Bacillus subtilis were tested by the 96-well plate dilution doubling method. The experiment result revealed that crystal of compound 2b was a kind of twin crystal, and the two pyridine bis(4-amino-1,2,4-triazole-3-thioethers) had good bacteriostatic activities to Escherichia coli and Candida albican in the range of test concentration, but had no antibacterial activities against Staphylococcus aureus and Bacillus subtilis.