Synthesis, characterization and computational studies on (E)-4-(1-((2-hydroxyphenyl)imi no) hexyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one

IF 4 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Structure Pub Date : 2024-11-05 DOI:10.1016/j.molstruc.2024.140552

Nkechinyere N. Ukwueze , Chigozie J. Ezeorah , Ebuka L. Onyeyilim , Chiamaka P. Uzoewulu , Uchechukwu C. Okoro , Pius O. Ukoha , Nnaemeka Nnaji , Chigozie J.O. Anarado , Necmi Dege , Nnamdi L. Obasi , Albert O. Ugwu , Ngozi M. Onyeisi , Kevin Lobb , Oguejiofo T. Ujam

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引用次数: 0

Abstract

A coupling precursor, 4-hexanoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, 1 synthesized by the reaction of 3-methyl-1-phenyl-1H-pyrazol-5-one with hexanoyl chloride was reacted with 2-aminophenol to synthesize (E)-4-(1-((2-hydroxyphenyl)imino)hexyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, 1a. The compounds were characterized by conventional spectroscopic techniques, ¹H and ¹³C NMR, UV–Visible, FTIR spectroscopy and single crystal X-ray crystallograpic structural determinations and computational techniques. To augment the experimental data, DFT calculations were carried. Molecular dockings were used to predict the interactions between, 1a with some biological targets. The binding free energies in the Plasmepsin II active sites indicated anti−malarial activity against P. falciparum in epidermal growth factor receptor (EGFR) inhibition, anti-inflammatory properties against human peroxiredoxin 5, and anticancer properties. With binding energies less than −5.00 kcal/mol, the results indicate that 1a is a potential drug target for anti-inflammatory, anti-malarial and anti-cancer properties.

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(E)-4-(1-((2-羟基苯基)亚氨基)己基)-5-甲基-2-苯基-2,4-二氢-3H-吡唑-3-酮的合成、表征和计算研究

由 3-甲基-1-苯基-1H-吡唑-5-酮与己酰氯反应合成的偶联前体 4-己酰氯-5-甲基-2-苯基-2,4-二氢-3H-吡唑-3-酮 1 与 2-氨基苯酚反应合成了 (E)-4-(1-((2-羟基苯基)亚氨基)己基)-5-甲基-2-苯基-2,4-二氢-3H-吡唑-3-酮 1a。这些化合物通过常规光谱技术、1H 和 13C NMR、紫外-可见光、傅立叶变换红外光谱以及单晶 X 射线晶体结构测定和计算技术进行表征。为了扩充实验数据，还进行了 DFT 计算。分子对接用于预测 1a 与一些生物靶标之间的相互作用。Plasmepsin II 活性位点的结合自由能表明，它对恶性疟原虫有抗疟活性，对表皮生长因子受体（EGFR）有抑制作用，对人类过氧化物酶 5 有抗炎特性，还具有抗癌特性。结合能小于-5.00 kcal/mol，结果表明 1a 是一种具有抗炎、抗疟疾和抗癌特性的潜在药物靶标。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.