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以异吲哚酮-芳基腙配体为生物活性试剂和苯乙烯环氧化有效催化剂的Fe(II)和Cr(II)配合物的合成与表征

Synthesis and characterization of Fe(II)- and Cr(II)-complexes with isatin-aryl hydrazone ligand as bio-reactive reagents and effective catalysts for styrene epoxidation.

作者信息

Adam Mohamed Shaker S

机构信息

Department of Chemistry, College of Science, King Faisal University, P.O. Box 400, Al-Ahsa 31982, Saudi Arabia.

出版信息

Bioorg Chem. 2025 Aug;163:108625. doi: 10.1016/j.bioorg.2025.108625. Epub 2025 May 23.

DOI:10.1016/j.bioorg.2025.108625
PMID:40446709
Abstract

For the facile preparative description of aryl-hydrazones and their interesting coordination modes, a new aryl-hydrazone derivative (HLhdzh) was formed from the combination of 2,4-dihydroxybenzaldehyde with isatin-hydrazide. HLhdzh coordinated to Fe and Cr ions to give two new metal(II)-complexes (as Fe(Lhdzh) and Cr(Lhdzh), respectively). Their chemical structure was confirmed with perspective spectroscopic tools, and by measuring their purity via micro-elemental investigations. Against the proliferative progress of human cancer cell lines and the namely prevalent microbial series, the bio-potential of HLhdzh, Fe(Lhdzh), and Cr(Lhdzh) was demonstrated, highlighting the considerable action of the nuclearity in Fe(Lhdzh) and Cr(Lhdzh) compared to that of HLhdzh. Also, the bio-potential of HLhdzh, Fe(Lhdzh), and Cr(Lhdzh) was studied within their interacting process with ctDNA (deoxyribonucleic acid) spectrophotometrically and viscometrically. Their antireflective action against the tumors and microorganisms was successfully reported, within the inhabited zoon areas (against the microbes) and the IC concentrations (against the tumors). Assigning the values of Gibbs' free energy and binding constant, the nature of their interacting features was addressed, referring to the presented mono-nuclear ion (nuclearity effect) for modification of their complexes' interaction. For the catalytic oxygenative systems, the homogeneous catalytic potential of Fe(Lhdzh) and Cr(Lhdzh) was evaluated in the oxygenative progress of styrene with HO to give styrene-epoxide at 85 °C. The yield percentage of styrene-epoxide catalyzed by Fe(Lhdzh) or Cr(Lhdzh) was obtained using GC-MS, affording 88 and 85 % after 5 h, respectively. The reactivity variation for each catalyst was attributed to the influence of nuclear nature (synergistic influence), which was supported by a proper mechanism, spectroscopically.

摘要

为了便于对芳基腙及其有趣的配位模式进行制备描述,由2,4 - 二羟基苯甲醛与异吲哚酮酰肼反应生成了一种新的芳基腙衍生物(HLhdzh)。HLhdzh与铁离子和铬离子配位,分别得到两种新的金属(II)配合物(即Fe(Lhdzh)和Cr(Lhdzh))。通过相关光谱工具确定了它们的化学结构,并通过微量元素分析测定了它们的纯度。针对人类癌细胞系的增殖进程以及常见的微生物菌株,研究了HLhdzh、Fe(Lhdzh)和Cr(Lhdzh)的生物活性,结果表明与HLhdzh相比,Fe(Lhdzh)和Cr(Lhdzh)中的核性具有显著作用。此外,还通过分光光度法和粘度法研究了HLhdzh、Fe(Lhdzh)和Cr(Lhdzh)与ctDNA(脱氧核糖核酸)相互作用过程中的生物活性。成功报道了它们在人畜共居区域(针对微生物)和IC浓度(针对肿瘤)内对肿瘤和微生物的抗反射作用。通过确定吉布斯自由能和结合常数的值,探讨了它们相互作用特征的性质,并参考所呈现的单核离子(核性效应)来修饰其配合物的相互作用。对于催化氧化体系,在85°C下,以HO对苯乙烯进行氧化反应生成苯乙烯环氧化物的过程中,评估了Fe(Lhdzh)和Cr(Lhdzh)的均相催化潜力。使用GC - MS测定了由Fe(Lhdzh)或Cr(Lhdzh)催化生成苯乙烯环氧化物的产率,5小时后分别为88%和85%。每种催化剂的反应活性变化归因于核性质的影响(协同影响),这在光谱学上有适当的机制作支撑。

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