Abstract

A series of 5-(2-chloroquinolin-3-yl)-1,3,4-oxadiazole-2-amine (IIIa–IIIj) with different biological activities were designed and synthesized through the cyclization of semicarbazone. All the newly synthesized compounds were characterized by elemental analysis, ¹H NMR, ¹³C NMR, FT-IR, and mass spectrometry. All the newly synthesized final compounds (IIIa–IIIj) were screened for in vitro antimicrobial activity by diffusion into agar wells using Gentamicin as the antibacterial agent and Fluconazole as the antifungal control. In addition, selected compounds were screened for antitubercular activity using Microplate Alamar Blue Assay (MABA). All the compounds were evaluated computationally for drug similarity using various pharmacokinetic studies and ADME-T characterization, then tested in vitro against Gram+ bacteria (Staphylococcus aureus and Bacillus subtilis), Gram– bacteria (S. typhi and P. aeruginosa), fungi (Aspergillus niger and Fusarium), as well as the Mycobacterium tuberculosis H37Rv strain, provided important information about activity against these strains. In the current study, we have discussed the method for the synthesis of 1,3,4-oxadiazole derivatives and summarized the role of compounds (IIIa), (IIIb), (IIId), (IIIg), (IIIh), and (IIIi) as potential antibacterial and antitubercular agents. We put forward further in vivo evaluation and biological activity evaluation for their use against these pathogens.

中文翻译：

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取代的 5-(2-氯喹啉-3-基)-1,3,4-恶二唑-2-胺的合成和表征：计算、计算机 ADME、分子对接和生物活性

摘要

通过缩氨基脲环化，设计合成了一系列具有不同生物活性的5-(2-氯喹啉-3-基)-1,3,4-恶二唑-2-胺( IIIa–IIIj )。所有新合成的化合物均通过元素分析、¹ H NMR、¹³ C NMR、FT-IR 和质谱进行了表征。使用庆大霉素作为抗菌剂和氟康唑作为抗真菌对照，通过扩散到琼脂孔中来筛选所有新合成的最终化合物（IIIa-IIIj ）的体外抗菌活性。此外，使用微孔板阿拉玛蓝测定 (MABA) 筛选选定化合物的抗结核活性。使用各种药代动力学研究和 ADME-T 表征对所有化合物的药物相似性进行计算评估，然后针对革兰氏阳性细菌（金黄色葡萄球菌和枯草芽孢杆菌）、革兰氏阴性细菌（伤寒沙门氏菌和铜绿假单胞菌）、真菌（曲霉）进行体外测试黑日菌和镰刀菌）以及结核分枝杆菌H37Rv 菌株提供了有关针对这些菌株的活性的重要信息。在本研究中，我们讨论了1,3,4-恶二唑衍生物的合成方法，并总结了化合物( IIIa )、( IIIb )、( IIId )、( IIIg )、( IIIh )和( IIIi）作为潜在的抗菌剂和抗结核剂。我们提出了进一步的体内评价和生物活性评价，以评价它们针对这些病原体的用途。