1, 2, 3-三唑类磺胺的合成及抗菌活性

Synthesis and Antibacterial Activities of Sulfonamides Derivatives Bearing 1, 2, 3-Triazole Moiety

摘要:

以磺胺(4-氨基苯磺酰胺)为原料，其与氯乙酰氯反应得到中间体2-氯-N-(4-氨磺酰基苯基)乙酰胺(Ⅱ)，然后(Ⅱ)与叠氮钠和端基炔“一锅法”反应合成了10个1, 2, 3-三唑类磺胺化合物(Ⅲa~Ⅲj)，利用FTIR、1H NMR、13C NMR和ESI-MS对产物结构进行表征。采用二倍稀释法测定目标化合物的抗菌活性，结果表明：产物对金黄色葡萄球菌和大肠杆菌表现出一定的抗菌活性，特别是2-(4-(3-氟苯基)-1H-1, 2, 3-三唑-1-基)-N-(4-氨磺酰基苯基)乙酰胺(Ⅲh)对大肠杆菌的的MIC为0.25 μg/mL，与阳性对照药环丙沙星相当。

Abstract:

The Intermediate 2-chloro-N-(4-sulfamoylphenyl)acetamide(II) was obtained by the reaction of sulfanilamide and chloroacetyl chloride. Ten 1, 2, 3-triazolyl sulfonamides were prepared using a known one-pot procedure starting from (II), sodium azide and terminal alkynes. The target compounds were characterized by FTIR, 1H NMR, 13C NMR and ESI-MS. The minimal inhibitory concentrations (MIC) of target compounds against S.aureus and E.coli were determined with double broth dilution method. The results showed that all the tested compounds exhibited a certain antibacterial activities. In particular, 2-(4-(3-fluorophenyl)-1H-1, 2, 3-triazol-1- yl)-N-(4- sulfamoylphenyl)acetamide (IIIh) possessed similar activity against E.coli compared with the positive control drug (ciprofloxacin 0.25 μg/mL).