Abstract Some new 3,4,5-trisubstituted 1,2,4-triazole derivatives were synthesized and studied for their antimicrobial activity. The lead compounds were obtained starting from 8-hydroxyquinoline and ethyl 2-chloroacetate. The obtained ester compound (1) first reacted with hydrazine hydrate (2) then with phenyl isothiocyanate (3). Ring closure by KOH led to 3-mercapto-1,2,4-triazole derivative (4). Lastly, it reacted with 2-chloro-N-(substituted (benzo)/thiazole)acetamide derivatives to obtain the final compounds (5a–j). The structural elucidation of the compounds was performed by 1H NMR and 13C NMR spectroscopy and high resolution mass spectrometry techniques and elemental analysis. The synthesized compounds were investigated for their antimicrobial activities against seven bacteria and four fungi. As a result of the activity studies, it was observed that compounds N-(6-nitrobenzothiazol-2-yl)-2-[[4-phenyl-5-((quinolin-8-yloxy)methyl)-4H-1,2,4-triazol-3-yl]thio]acetamide (5a) and N-(6-fluorobenzothiazol-2-yl)-2-[[4-phenyl-5-((quinolin-8-yloxy)methyl)-4H-1,2,4-triazol-3-yl]thio]acetamide (5d) were the most active molecules. Also, the antifungal activity of the compounds was found to be higher than their antibacterial activity although lower than the standard drug’s potential. Additionally, the physicochemical properties of the compounds were calculated which were evaluated to be at a suitable range for oral administration. Graphical Abstract

中文翻译：

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新型含喹啉环的3,4,5-三取代三唑衍生物的合成及抗菌活性评价

摘要 合成了一些新的3,4,5-三取代1,2,4-三唑衍生物并研究了它们的抗菌活性。先导化合物是从 8-羟基喹啉和 2-氯乙酸乙酯开始获得的。所得酯化合物(1)首先与水合肼(2)反应，然后与异硫氰酸苯酯(3)反应。KOH 闭环产生 3-巯基-1,2,4-三唑衍生物 (4)。最后，它与 2-氯-N-（取代（苯并）/噻唑）乙酰胺衍生物反应得到最终化合物（5a-j）。通过1H NMR和13C NMR光谱和高分辨率质谱技术和元素分析进行​​化合物的结构解析。研究了合成的化合物对七种细菌和四种真菌的抗菌活性。作为活动研究的结果，观察到化合物 N-(6-nitrobenzothiazol-2-yl)-2-[[4-phenyl-5-((quinolin-8-yloxy)methyl)-4H-1,2,4-triazol-3-基]硫代]乙酰胺(5a)和N-(6-氟苯并噻唑-2-基)-2-[[4-苯基-5-((喹啉-8-基氧基)甲基)-4H-1,2,4-三唑-3-基]硫代]乙酰胺（5d）是最活跃的分子。此外，发现这些化合物的抗真菌活性高于它们的抗菌活性，尽管低于标准药物的潜力。此外，计算了化合物的理化性质，其被评估为在适合口服给药的范围内。图形概要 4-三唑-3-基]硫代]乙酰胺 (5d) 是最活跃的分子。此外，发现这些化合物的抗真菌活性高于它们的抗菌活性，尽管低于标准药物的潜力。此外，计算了化合物的理化性质，其被评估为在适合口服给药的范围内。图形概要 4-三唑-3-基]硫代]乙酰胺 (5d) 是最活跃的分子。此外，发现这些化合物的抗真菌活性高于它们的抗菌活性，尽管低于标准药物的潜力。此外，计算了化合物的理化性质，其被评估为在适合口服给药的范围内。图形概要