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3-(4-哌嗪-1-基-苯基)-s-三唑并[3,4-b][1,3,4]噻二唑盐酸盐的合成与抗菌活性

[Synthesis and antibacterial activity of 3-(4-piperazin-1-yl-phenyl)-s-triazolo [3,4-b] [1,3,4] thiadiazole hydrochlorides].

作者信息

Hu Guo-Qiang, Sun Mao-Feng, Xie Song-Qiang, Huang Wen-Long, Zhang Hui-Bin

机构信息

Institute of Pharmacy, Henan University, Kaifeng 475004, China.

出版信息

Yao Xue Xue Bao. 2007 Jan;42(1):54-7.

Abstract

To study the synthetic method and antibacterial activity of water-soluble fused heterocyclic compounds containing piperazine group, the nucleophilic substitution of 3-(4-chlorophenyl)-6-substituted-s-triazolo-[3, 4-b] [1, 3, 4] thiadiazoles (2a - n) with piperazine in the presence of phase transfer catalyst TBAI afforded 3-(4-piperazin-1-yl-phenyl)-6-substituted-s-triazolo [3, 4-b] [1, 3, 4] thiadiazole and then followed by acid treatment afforded 3-(4-piperazin-1-yl-phenyl)-6-substituted-s-triazolo [ 3, 4-b] [1, 3, 4] thiadiazole hydrochlorides (3a - n). Twenty-eight new compounds were synthesized and their structures were confirmed by IR, 1H NMR, MS and element analysis. The in vitro antibacterial activities of all newly synthesized compounds were tested against Gram positive bacteria and Gram negative bacteria with the standard 2-fold agar dilution method. Fourteen title compounds exhibited potential antibacterial activities in vitro. The structures of these compounds needed to be further optimized.

摘要

为研究含哌嗪基团的水溶性稠杂环化合物的合成方法及抗菌活性,在相转移催化剂四丁基碘化铵存在下,3-(4-氯苯基)-6-取代-s-三唑并-[3,4-b][1,3,4]噻二唑(2a - n)与哌嗪发生亲核取代反应,得到3-(4-哌嗪-1-基-苯基)-6-取代-s-三唑并[3,4-b][1,3,4]噻二唑,然后经酸处理得到3-(4-哌嗪-1-基-苯基)-6-取代-s-三唑并[3,4-b][1,3,4]噻二唑盐酸盐(3a - n)。合成了28个新化合物,其结构经红外光谱、核磁共振氢谱、质谱及元素分析确证。采用标准的2倍琼脂稀释法,对所有新合成化合物进行了体外抗革兰氏阳性菌和革兰氏阴性菌活性测试。14个目标化合物表现出潜在的体外抗菌活性。这些化合物的结构有待进一步优化。

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