Molecular Diversity ( IF 3.9 ) Pub Date : 2021-01-07 , DOI: 10.1007/s11030-020-10157-4 Abrar Ul Hassan 1 , Sajjad Hussain Sumrra 1 , Muhammad Nadeem Zafar 1 , Muhammad Faizan Nazar 1, 2 , Ehsan Ullah Mughal 1 , Muhammad Naveed Zafar 3 , Mazhar Iqbal 4
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Abstract
During the present investigation, two new sulfonamide-based Schiff base ligands, 4-{[(2-hydroxy-3-methoxyphenyl)methylidene]amino}-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide (L1) and 4-{[1-(2-hydroxyphenyl)ethylidene]amino}-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide (L2), have been synthesized and coordinated with the transition metals (V, Fe, Co, Ni, Cu and Zn). The ligands were characterized by their physical (color, melting point, yield and solubility), spectral (UV–Vis, FT-IR, LC–MS, 1H NMR and 13C NMR) and elemental data. The structures of the metal complexes (1)–(12) were evaluated through their physical (magnetic and conductance), spectral (UV–Vis, FT-IR and LC–MS) and elemental data. The molecular geometries of ligands and their selected metal complexes were optimized at their ground state energies by B3LYP level of density functional theory (DFT) utilizing 6-311+G (d, p) and LanL2DZ basis set. The first principle study has been discussed for the electronic properties, the molecular electrostatic possibilities as well as the quantum chemical identifiers. An obvious transition of intramolecular charge had been ascertained from the occupied to the unoccupied molecular orbitals. The UV–Vis analysis was performed through time-dependent density functional theory (TD-DFT) by CAM-B3LYP/6-311+G (d, p) function. The in vitro antimicrobial activity was studied against two fungal (Aspergillus niger and Aspergillus flavus) and four bacterial (Staphylococcus aureus, Klebsiela pneumoniae, Escherichia coli and Bacillus subtilis) species. The antioxidant activity was executed as antiradical DPPH scavenging activity (%), total iron reducing power (%) and total phenolic contents (mg GAE g−1). Additionally, enzyme inhibition activity was done against four enzymes (Protease, α-Amylase, Acetylcholinesterase and Butyrylcholinesterase). All the synthetic products exhibited significant bioactivity which were found to enhance upon chelation due to phenomenon of charge transfer from metal to ligand.
Graphic abstract
中文翻译：
作为强效药物的新型有机硫金属化合物：合成、分子建模、光谱、抗菌、药物相似性和 DFT 分析
摘要
在目前的研究中，两个新的基于磺胺的席夫碱配体，4-{[(2-羟基-3-甲氧基苯基)亚甲基]氨基}-N-(1,3-噻唑-2-基)苯-1-磺胺e ( L 1 ) 和4-{[1-(2-羟基苯基)亚乙基]氨基}-N-(1,3-thiazol-2-yl)benzo-1-sulfonamide ( L 2 ), 已合成并配位过渡金属（V、Fe、Co、Ni、Cu 和 Zn）。配体通过其物理（颜色、熔点、产率和溶解度）、光谱（UV-Vis、FT-IR、LC-MS、1 H NMR 和13 C NMR）和元素数据进行表征。金属配合物的结构 ( 1 )–( 12) 通过其物理（磁性和电导）、光谱（UV-Vis、FT-IR 和 LC-MS）和元素数据进行评估。利用 6-311+G (d, p) 和 LanL2DZ 基组，通过密度泛函理论 (DFT) 的 B3LYP 水平优化配体及其所选金属配合物的分子几何形状。已经讨论了电子特性、分子静电可能性以及量子化学标识符的第一原理研究。已确定分子内电荷从占据轨道到未占据分子轨道的明显转变。UV-Vis 分析通过 CAM-B3LYP/6-311+G (d, p) 函数通过时间依赖性密度泛函理论 (TD-DFT) 进行。研究了针对两种真菌的体外抗菌活性（黑曲霉和黄曲霉）和四种细菌（金黄色葡萄球菌、肺炎克雷伯菌、大肠杆菌和枯草芽孢杆菌）。抗氧化活性以抗自由基DPPH清除活性(%)、总铁还原能力(%)和总酚含量(mg GAE g -1 )表示。此外，对四种酶（蛋白酶、α-淀粉酶、乙酰胆碱酯酶和丁酰胆碱酯酶）进行酶抑制活性。所有合成产物都表现出显着的生物活性，由于从金属到配体的电荷转移现象，发现它们在螯合时会增强。
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