Chemistry Department, Faculty of Science, Alexandria University, Ibrahimia P.O. Box 426, Alexandria 21321, Egypt.
Molecules. 2011 Jun 28;16(7):5496-506. doi: 10.3390/molecules16075496.
2-Amino-5-(2-aryl-2H-1,2,3-triazol-4-yl)-1,3,4-thiadiazoles 2-4 have been synthesized by the reaction of 2-aryl-2H-1,2,3-triazole-4-carboxylic acids 1 with thiosemicarbazide. Their reaction with phenacyl (p-substituted phenacyl) bromides led to formation of the respective 6-aryl-2-(2-aryl-2H-1,2,3-triazol-4-yl)imidazo[2,1-b]-1,3,4-thiadiazoles 5. Reactivity of the latter fused ring towards reaction with different electrophilic reagents afforded the corresponding 5-substituted derivatives 6-8. The structure of the above compounds was confirmed from their spectral characteristics. Some of these compounds were found to possess slight to moderate activity against the microorganisms Staphylococcus aureus, Candida albicans, Pseudomonas aeruginosa, and Escherichia coli.
2-氨基-5-(2-芳基-2H-1,2,3-三唑-4-基)-1,3,4-噻二唑 2-4 是通过 2-芳基-2H-1,2,3-三唑-4-羧酸 1 与氨基硫脲反应合成的。它们与苯乙酮(对取代苯乙酮)溴化物的反应导致相应的 6-芳基-2-(2-芳基-2H-1,2,3-三唑-4-基)咪唑并[2,1-b]-1,3,4-噻二唑 5 的形成。后者稠环的反应性对与不同亲电试剂的反应提供了相应的 5-取代衍生物 6-8。这些化合物的结构是从它们的光谱特征中得到证实的。其中一些化合物被发现对金黄色葡萄球菌、白色念珠菌、铜绿假单胞菌和大肠杆菌等微生物具有轻微到中等的活性。