2-Ferrocene-4-amine-1H-benzo[d]imidazole and their derivatives: Synthesis, biological and docking study

IF 2.4 3区化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR Polyhedron Pub Date : 2024-10-03 DOI:10.1016/j.poly.2024.117242

Mukesh Kawad , Sagar Sangani , Jigneshkumar Parmar , Ranjitsinh C. Dabhi , Prashant S. Arya , Nishith Teraiya , Sarfaraz Ahmed , Rakesh Kumar Ameta

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Abstract

An organometallic series based on 2-ferrocene-4-amine-1H-benzo[d]imidazole derivative has been synthesized and characterized through FTIR, ^H/CNMR, and LCMS. Their antimicrobial activity was assessed by testing them against B. subtills, Staphylococcus aureus, E. faecalis, S. marcescens, E. coli, K. pneumoniae, C. albicans, A. niger, Mucor sp. where they showed good zone of inhibition (ZOI) as compared to standards. The cytotoxicity of synthesized compounds was tested against Hela (cervical) and MCF-7 (breast) cancer cell lines where compound 5a and 5b displayed equivalent potency to the standard while 5e demonstrated highest cytotoxicity against both cell lines. Their comparative docking analysis with DNA suggested that docking score of 5e was −7.4 kcal/mol versus −6 kcal/mol of ethidium bromide, indicating that our designed compound acts via DNA intercalation.

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2-二茂铁-4-胺-1H-苯并[d]咪唑及其衍生物：合成、生物学和对接研究

我们合成了一个基于 2-二茂铁-4-胺-1H-苯并[d]咪唑衍生物的有机金属系列，并通过傅立叶变换红外光谱、H/CNMR 和 LCMS 对其进行了表征。通过测试这些衍生物对枯草杆菌、金黄色葡萄球菌、粪大肠杆菌、肉毒杆菌、大肠杆菌、肺炎双球菌、白僵菌、黑僵菌、粘孢子菌的抗菌活性，与标准物质相比，这些衍生物显示出良好的抑制区（ZOI）。合成的化合物对 Hela（宫颈癌）和 MCF-7（乳腺癌）细胞系进行了细胞毒性测试，结果表明化合物 5a 和 5b 与标准化合物的效力相当，而 5e 对这两种细胞系的细胞毒性最高。他们与 DNA 的对比对接分析表明，5e 的对接得分为 -7.4 kcal/mol，而溴化乙锭的对接得分为 -6 kcal/mol，这表明我们设计的化合物通过 DNA 插层发挥作用。

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来源期刊

Polyhedron 化学-晶体学

CiteScore

4.90

自引率

7.70%

发文量

515

审稿时长

2 months

期刊介绍： Polyhedron publishes original, fundamental, experimental and theoretical work of the highest quality in all the major areas of inorganic chemistry. This includes synthetic chemistry, coordination chemistry, organometallic chemistry, bioinorganic chemistry, and solid-state and materials chemistry. Papers should be significant pieces of work, and all new compounds must be appropriately characterized. The inclusion of single-crystal X-ray structural data is strongly encouraged, but papers reporting only the X-ray structure determination of a single compound will usually not be considered. Papers on solid-state or materials chemistry will be expected to have a significant molecular chemistry component (such as the synthesis and characterization of the molecular precursors and/or a systematic study of the use of different precursors or reaction conditions) or demonstrate a cutting-edge application (for example inorganic materials for energy applications). Papers dealing only with stability constants are not considered.