Department of Pharmaceutical Organic Chemistry, Mansoura University, Egypt.
Arch Pharm (Weinheim). 2011 Dec;344(12):821-9. doi: 10.1002/ardp.201100001. Epub 2011 Sep 20.
In research for promising antibacterial and antifungal compounds, a series of 2-aryl 3-[1,2,4]triazol-5-yl 4-thiazolidinones 1 were synthesized by a domino reaction of 5-amino-1H-[1,2,4]triazoles 3, aromatic aldehydes, and α-mercaptoacids in boiling toluene in the presence of molecular sieves 4 Å. Of the twenty novel 3-[1,2,4]triazol-5-yl 4-thiazolidinone derivatives, four compounds 2-benzo[d][1,3]dioxol-6-yl-3-[(3-morpholin-4-yl)-1H-1,2,4-triazol-5-yl)]-1,3-thiazolidin-4-one (1i), 2-(4-chlorophenyl)-5-methyl-3-[3-(4-methylpiperazin-1-yl)-1H-1,2,4-triazol-5-yl]-1,3-thiazolidin-4-one (1p), 2-benzo[d][1,3]dioxol-6-yl-3-[3-(4-methylpiperazin-1-yl)-1H-1,2,4-triazol-5-yl]-1,3-thiazolidin-4-one (1s), 2-benzo[d][1,3]dioxol-6-yl-5-methyl-3-[3-(4-methylpiperazin-1-yl)-1H-1,2,4-triazol-5-yl]-1,3-thiazolidin-4-one (1t) exhibited MICs of 4 µg/mL or less versus Mycobacterium tuberculosis. Moreover, these compounds were screened against Candida albicans. Compounds 1p, 1s gave MICs of 1 µg/mL or less, and were fungicidal. Finally, compound 1s was evaluated against an expanded fungal panel and showed good activity against Cryptococcus neoformans. In addition, compound 1s also appeared to be fungicidal against Aspergillus arrhizus, with MIC <1 µg/mL.
在寻找有前景的抗菌和抗真菌化合物的研究中，通过 5-氨基-1H-[1,2,4]三唑 3、芳香醛和α-巯基酸在分子筛 4Å 的存在下在沸腾的甲苯中的多米诺反应，合成了一系列 2-芳基 3-[1,2,4]三唑-5-基 4-噻唑烷酮 1。在二十种新型 3-[1,2,4]三唑-5-基 4-噻唑烷酮衍生物中，四种化合物 2-苯并[d][1,3]二恶唑-6-基-3-[(3-吗啉-4-基)-1H-1,2,4-三唑-5-基]-1,3-噻唑烷-4-酮（1i）、2-(4-氯苯基）-5-甲基-3-[3-(4-甲基哌嗪-1-基)-1H-1,2,4-三唑-5-基]-1,3-噻唑烷-4-酮（1p）、2-苯并[d][1,3]二恶唑-6-基-3-[3-(4-甲基哌嗪-1-基)-1H-1,2,4-三唑-5-基]-1,3-噻唑烷-4-酮（1s）、2-苯并[d][1,3]二恶唑-6-基-5-甲基-3-[3-(4-甲基哌嗪-1-基)-1H-1,2,4-三唑-5-基]-1,3-噻唑烷-4-酮（1t）对结核分枝杆菌的 MIC 值为 4μg/mL 或更低。此外，这些化合物还针对白色念珠菌进行了筛选。化合物 1p、1s 的 MIC 值为 1μg/mL 或更低，且具有杀菌作用。最后，化合物 1s 对扩大的真菌组进行了评估，对新型隐球菌表现出良好的活性。此外，化合物 1s 似乎对构巢曲霉也具有杀菌作用，MIC<1μg/mL。
