Synthesis, characterization, antimicrobial and antiproliferative activities, molecular docking, and physicochemical properties of novel hydrazinecarbothioamide derivatives

IF 4 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Structure Pub Date : 2025-05-23 DOI:10.1016/j.molstruc.2025.142774

G. Venkatesh , Khayala Mammadova , Manikandan Ayyar , J.N. Cheerlin Mishma , Lalitha Gnanasekaran , M. Santhamoorthy , P. Vennila

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引用次数: 0

Abstract

Novel hydrazinecarbothioamide derivatives of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-N-phenylhydrazinecarbothioamide (IPC) and (E)-2-(4-(2-morpholinoethoxy)benzylidene)-N-phenylhydrazinecarbothioamide (MPC) were synthesized and characterized using various spectroscopic techniques (FT-IR, UV–Visible and NMR spectroscopy). DFT calculations were carried out using the B3LYP/6–311++G(d,p) basis set to study the stability and reactivity of the compounds through the HOMO and LUMO energy values and MEP calculations were also carried out with the same basis set. In addition, topology analyses (ELF, LOL, and RDG) were performed using Multiwfn software in order to comprehend the molecules' reactivity. The antimicrobial activity was examined using both Gram-positive and Gram-negative bacterial strains. In vitro anticancer activity has been examined on breast cancer (MCF-7), colorectal carcinoma cancer (HCT-116) and cervical cancer (HeLa) cell lines. In anticancer assays, IPC was more effective against HCT-116 cell line, while MPC showed greater activity against MCF-7 cell line. Docking simulations for MPC and IPC were carried out against cancer-related protein structures (7XH3, 5YVO, and 6IWD).

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新型肼碳硫酰胺衍生物的合成、表征、抗菌和抗增殖活性、分子对接和理化性质

合成了(E)-2-（4-（1h -咪唑-1-基）苄基苄基）- n -苯基肼碳硫酰胺（IPC）和(E)-2-（4-（2-氨基酚乙氧基）苄基苄基）- n -苯基肼碳硫酰胺（MPC）的新型肼碳硫酰胺衍生物，并利用各种光谱技术（红外光谱、紫外可见光谱和核磁共振光谱）对其进行了表征。使用B3LYP/ 6-311 ++G（d,p）基集进行DFT计算，通过HOMO和LUMO能值研究化合物的稳定性和反应性，并使用相同的基集进行MEP计算。此外，使用Multiwfn软件进行拓扑分析（ELF、LOL和RDG），以了解分子的反应性。用革兰氏阳性和革兰氏阴性菌株检测其抗菌活性。对乳腺癌（MCF-7）、结直肠癌（HCT-116）和宫颈癌（HeLa）细胞系进行了体外抑癌活性研究。在抗癌实验中，IPC对HCT-116细胞系更有效，而MPC对MCF-7细胞系更有效。针对癌症相关蛋白结构（7XH3、5YVO和6IWD）进行了MPC和IPC对接仿真。

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来源期刊

Journal of Molecular Structure 化学-物理化学

CiteScore

7.10

自引率

15.80%

发文量

2384

审稿时长

45 days

期刊介绍： The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.