Synthesis of new benzimidazole derivatives containing 1,3,4-thiadiazole: their in vitro antimicrobial, in silico molecular docking and molecular dynamic simulations studies.

IF 2.3 3区环境科学与生态学 Q3 CHEMISTRY, MULTIDISCIPLINARY

SAR and QSAR in Environmental Research Pub Date : 2022-11-01 DOI:10.1080/1062936X.2022.2149620

U Acar Çevik, A Işık, A E Evren, Ö Kapusız, Ü D Gül, Y Özkay, Z A Kaplancıklı

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引用次数: 3

Abstract

A series of some new benzimidazole-1,3,4-thiadiazoles was synthesized. The structures of target substances were confirmed by using ¹H-NMR and ¹³С-NMR spectroscopy, mass spectrometry and elemental analysis. The synthesized compounds were evaluated for antimicrobial activity against six bacterial strains namely Escherichia coli (ATCC 25922), Klebsiella pneumoniae (ATCC 13883), Pseudomonas aeruginosa (ATCC 27853), Enterococcus faecalis (ATCC 2942), Bacillus subtilis (ATCC 6633), Staphylococcus aureus (ATCC 29213)and four fungal strains namely Candida albicans (ATCC 24433), Candida krusei (ATCC 6258), Candida parapsilosis (ATCC 22019) and Candida glabrata (ATCC 9). Antimicrobial data revealed that compounds 4f and 4i with MIC of < 0.97 µg/mL were found to be most effective against E. coli. Among the studied molecules, compounds 4f and 4i showed the best antifungal activity with MIC value of 1.95 µg/mL. Additionally, docking studies were performed towards the most promising compounds 4f and 4i, in the active site of DNA gyrase revealing strong interactions. A molecular dynamics (MD) simulation analysis was also used to investigate the dynamic nature, binding interaction, and protein-ligand stability.

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含1,3,4-噻二唑的新型苯并咪唑衍生物的合成:体外抗菌、硅分子对接及分子动力学模拟研究。

合成了一系列新的苯并咪唑-1,3,4-噻二唑。目的物质的结构通过1H-NMR和13С-NMR光谱、质谱和元素分析得到了证实。合成的化合物对大肠杆菌(ATCC 25922)、肺炎克雷伯菌(ATCC 13883)、铜绿假单胞菌(ATCC 27853)、粪肠球菌(ATCC 2942)、枯草芽孢杆菌(ATCC 6633)、金黄色葡萄球菌(ATCC 29213) 6株细菌和白色念珠菌(ATCC 24433)、克鲁氏念珠菌(ATCC 6258)、抗菌数据显示，MIC < 0.97 μ g/mL的化合物4f和4i对大肠杆菌最有效。其中化合物4f和4i的抗真菌活性最强，MIC值为1.95µg/mL。此外，对最有希望的化合物4f和4i进行了对接研究，在DNA回转酶的活性位点发现了强相互作用。分子动力学(MD)模拟分析也用于研究动态性质，结合相互作用和蛋白质-配体稳定性。

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来源期刊

SAR and QSAR in Environmental Research 环境科学-毒理学

CiteScore

5.20

自引率

20.00%

发文量

审稿时长

>24 weeks

期刊介绍： SAR and QSAR in Environmental Research is an international journal welcoming papers on the fundamental and practical aspects of the structure-activity and structure-property relationships in the fields of environmental science, agrochemistry, toxicology, pharmacology and applied chemistry. A unique aspect of the journal is the focus on emerging techniques for the building of SAR and QSAR models in these widely varying fields. The scope of the journal includes, but is not limited to, the topics of topological and physicochemical descriptors, mathematical, statistical and graphical methods for data analysis, computer methods and programs, original applications and comparative studies. In addition to primary scientific papers, the journal contains reviews of books and software and news of conferences. Special issues on topics of current and widespread interest to the SAR and QSAR community will be published from time to time.