Synthesis and structural elucidation of 1,2-naphthoquinone derivatives, Schiff base complexes and ternary complexes with 8-hydroxyquinoline: comparative studies of their antimicrobial, anti-inflammatory and anti-diabetic activities

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2023-09-02 DOI:10.1007/s11243-023-00551-w

Seema, Shobhana Sharma, Poonam Yadav, Suman Kumari, Mamta Ranka

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Abstract

Herein, a new derivative of 1,2-naphthoquinone with semicarbazide and its Schiff base complexes and ternary complexes have been synthesized with some transition metals such as Ni(II), Co(II) and Zn(II) by using the conventional reflux method and 8-hydroxyquinoline (8-HQ) as a secondary ligand for ternary complexes. All the compounds were characterized using elemental analysis, molar conductance, melting point, Powder XRD, magnetic moment measurement and various spectral techniques such as FTIR, ¹³C NMR, ¹H NMR, and Mass Spectra. The specific peak of the enolic proton in ¹H NMR spectra of the tridentate ligand (L) explained the amido-iminol tautomerism in semicarbazone. In addition, powder XRD analysis and TGA confirmed the crystalline nature and the thermal study of metal chelates, respectively. In vitro, all the compounds were screened for antimicrobial (against bacterial strains: S. aureus and E. coli; Fungal strain: A. niger), anti-diabetic and anti-inflammatory activity with their obtained IC₅₀ values and compared with Acarbose and Aspirin standard drugs. Bioactivities of azomethine containing free ligand (L), their Schiff base complexes and ternary metal chelates were compared to each other. Free Schiff base (L) was found most potent for all selective bioactivities compared to their all-metal complexes, except Ni (II) Schiff base complex showed excellent activity against C. albicans.

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1,2-萘醌衍生物、希夫碱络合物以及与 8-羟基喹啉的三元络合物的合成与结构解析：其抗菌、抗炎和抗糖尿病活性的比较研究

本文采用常规回流法，以8-羟基喹啉（8-HQ）为三元配合物的二级配体，与Ni（II）、Co（II）和Zn（II）等过渡金属合成了1，2-萘醌与氨基脲的新衍生物及其席夫碱配合物和三元配合物。使用元素分析、摩尔电导、熔点、粉末XRD、磁矩测量和各种光谱技术如FTIR、13C NMR、1H NMR和质谱对所有化合物进行了表征。三齿配体（L）的1H NMR谱中烯醇质子的特定峰解释了氨基脲中酰胺-亚氨基醇的互变异构。此外，粉末XRD分析和TGA分别证实了金属螯合物的结晶性质和热研究。在体外，用获得的IC50值筛选所有化合物的抗菌活性（针对细菌菌株：金黄色葡萄球菌和大肠杆菌；真菌菌株：黑曲霉）、抗糖尿病和抗炎活性，并与阿卡波糖和阿司匹林标准药物进行比较。比较了含自由配体（L）的甲亚胺、它们的席夫碱配合物和三元金属螯合物的生物活性。与所有金属配合物相比，游离希夫碱（L）对所有选择性生物活性都是最有效的，但Ni（II）希夫碱配合物对白色念珠菌表现出优异的活性。

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.