Dincel Efe Doğukan, Kuran Ebru Didem, Dinç Harika Öykü, Başoğlu Faika, Güler Emrah, Ulusoy Güzeldemirci Nuray
İstanbul University Faculty of Pharmacy, Department of Pharmaceutical Chemistry, İstanbul, Türkiye.
Fenerbahçe University Faculty of Pharmacy, Department of Pharmaceutical Chemistry, İstanbul, Türkiye.
Turk J Pharm Sci. 2025 Sep 5;22(4):226-234. doi: 10.4274/tjps.galenos.2025.90304.
This study focused on synthesizing and characterizing novel thiosemicarbazide derivatives containing a 1,2,4-triazole moiety and evaluating their antimicrobial activity against several bacterial strains. The research aimed to identify key structural features that enhance antimicrobial efficacy through structure-activity relationship analysis and identify the minimum inhibitory concentration (MIC) of the most potent compounds to assess their potential for further development as antimicrobial agents.
Nine novel thiosemicarbazide derivatives containing a 1,2,4-triazole moiety were synthesized by reacting 1,2,4-triazole derivatives with thiosemicarbazide precursors, and the products were characterized using infrared spectroscopy, proton nuclear magnetic resonance (H-NMR), carbon-13 nuclear magnetic resonance (C-NMR) spectroscopy, and elemental analysis. The antimicrobial activity of these compounds (5a-i) was tested against , , , and using microdilution, disk diffusion, and broth microdilution methods. Dimethyl sulfoxide was used as a negative control, and Vancomycin and Meropenem were used as positive controls, with all results converted to µM for consistent analysis.
The synthesized thiosemicarbazide derivatives (5a-i) were confirmed to be structurally correct through Fourier-transform infrared spectroscopy, H-NMR, and C-NMR spectroscopy. Among the tested compounds, 5e (4-bromophenyl) and 5g (n-propyl) showed significant antimicrobial activity, with 5g exhibiting the strongest effects against and . Other derivatives, such as 5b (4-NOPh), 5c (4-FPh), and 5d (4-ClPh), showed moderate activity, while no significant activity was observed against or .
The study successfully synthesized a series of novel thiosemicarbazide derivatives with a 1,2,4-triazole moiety and evaluated their antimicrobial potential. Compounds 5e and 5g exhibited significant antibacterial activity, particularly against and , with MIC values in the low micromolar range. These findings suggest that the compounds hold promise as potential antimicrobial agents, and further studies should focus on optimizing their efficacy and exploring their mechanism of action.
本研究着重于合成并表征含1,2,4 - 三唑部分的新型硫代氨基脲衍生物，并评估它们对几种细菌菌株的抗菌活性。该研究旨在通过构效关系分析确定增强抗菌效力的关键结构特征，并确定最有效化合物的最低抑菌浓度（MIC），以评估它们作为抗菌剂进一步开发的潜力。
通过使1,2,4 - 三唑衍生物与硫代氨基脲前体反应，合成了九种含1,2,4 - 三唑部分的新型硫代氨基脲衍生物，并使用红外光谱、质子核磁共振（H - NMR）、碳 - 13核磁共振（C - NMR）光谱和元素分析对产物进行了表征。使用微量稀释法、纸片扩散法和肉汤微量稀释法测试了这些化合物（5a - i）对金黄色葡萄球菌、大肠杆菌、铜绿假单胞菌和白色念珠菌的抗菌活性。二甲基亚砜用作阴性对照，万古霉素和美罗培南用作阳性对照，所有结果均转换为微摩尔（µM）以便进行一致的分析。
通过傅里叶变换红外光谱、H - NMR和C - NMR光谱证实合成的硫代氨基脲衍生物（5a - i）结构正确。在测试的化合物中，5e（4 - 溴苯基）和5g（正丙基）表现出显著的抗菌活性，其中5g对金黄色葡萄球菌和大肠杆菌表现出最强的作用。其他衍生物，如5b（4 - NOPh）、5c（4 - FPh）和5d（4 - ClPh）表现出中等活性，而对白色念珠菌或铜绿假单胞菌未观察到显著活性。
该研究成功合成了一系列含1,2,4 - 三唑部分的新型硫代氨基脲衍生物，并评估了它们的抗菌潜力。化合物5e和5g表现出显著的抗菌活性，特别是对金黄色葡萄球菌和大肠杆菌，MIC值在低微摩尔范围内。这些发现表明这些化合物有望成为潜在的抗菌剂，进一步的研究应集中在优化它们的效力并探索其作用机制上。
