Sztanke Krzysztof, Pasternak Kazimierz, Sidor-Wójtowicz Anna, Truchlińska Janina, Jóźwiak Krzysztof
Department of Synthesis and Chemical Technology of Pharmaceutical Substances, Medical University, 6 Staszica Str, 20-081 Lublin, Poland.
Bioorg Med Chem. 2006 Jun 1;14(11):3635-42. doi: 10.1016/j.bmc.2006.01.019. Epub 2006 Feb 7.
1-Arylimidazolidine-2-thiones (1a-g) were synthesized by the condensation reaction of N-arylethylenediamines with carbon disulfide in xylene medium. Their further alkylation with methyl iodide led to the formation of some biologically active 1-aryl-2-methylthio-imidazolines (2a-g). The 7-(4-methylphenyl)-3-methylthio-5H-6,7-dihydroimidazo[2,1-c][1,2,4]triazole (4b) was obtained by the alkylation of the respective 7-(4-methylphenyl)-2,5,6,7-tetrahydroimidazo[2,1-c][1,2,4]triazol-3(H)-thione (3b) with methyl iodide. Antimicrobial activities of 1-aryl-2-methylthio-imidazolines (2a-g) and the 7-(4-methylphenyl)-3- methylthio-5H-6,7-dihydroimidazo[2,1-c][1,2,4]triazole (4b) are presented. All tested compounds showed MIC in the range of 11.0-89.2 microM. Compounds 2a,e were found to be equipotent to chloramphenicol in vitro, whereas 2a,c,e-g and 4b showed superior activity (MIC) to ampicillin.
通过N - 芳基乙二胺与二硫化碳在二甲苯介质中的缩合反应合成了1 - 芳基咪唑烷 - 2 - 硫酮（1a - g）。它们与碘甲烷进一步烷基化反应生成了一些具有生物活性的1 - 芳基 - 2 - 甲硫基咪唑啉（2a - g）。通过相应的7 -（4 - 甲基苯基）- 2,5,6,7 - 四氢咪唑并[2,1 - c][1,2,4]三唑 - 3（H）- 硫酮（3b）与碘甲烷烷基化反应得到了7 -（4 - 甲基苯基）- 3 - 甲硫基 - 5H - 6,7 - 二氢咪唑并[2,1 - c][1,2,4]三唑（4b）。介绍了1 - 芳基 - 2 - 甲硫基咪唑啉（2a - g）和7 -（4 - 甲基苯基）- 3 - 甲硫基 - 5H - 6,7 - 二氢咪唑并[2,1 - c][1,2,4]三唑（4b）的抗菌活性。所有测试化合物的最低抑菌浓度（MIC）在11.0 - 89.2 microM范围内。发现化合物2a、e在体外与氯霉素等效，而2a、c、e - g和4b对氨苄西林表现出更高的活性（MIC）。
