Synthesis, characterization, and biological screening of metal complexes of novel sulfonamide derivatives: Experimental and theoretical analysis of sulfonamide crystal

化学 磺胺 单斜晶系 齿合度 晶体结构 结晶学 配体(生物化学) 立体化学 生物化学 受体
作者
Sajjad Hussain Sumrra,Abrar U. Hassan,Muhammad Imran,Muhammad Khalid,Ehsan Ullah Mughal,Muhammad Nadeem Zafar,Muhammad Nawaz Tahir,Muhammad Asam Raza,Ataualpa Albert Carmo Braga
出处
期刊:Applied Organometallic Chemistry [Wiley]
卷期号:34 (7) 被引量:48
标识
DOI:10.1002/aoc.5623
摘要

This study reports the synthesis of sulfonamide‐derived Schiff bases as ligands L 1 and L 2 as well as their transition metal complexes [VO(IV), Fe(II), Co(II), Ni(II), Cu(II), and Zn(II)]. The Schiff bases (4‐{ E ‐[(2‐hydroxy‐3‐methoxyphenyl)methylidene]amino}benzene‐1‐sulfonamide ( L 1 ) and 4‐{[(2‐hydroxy‐3‐methoxyphenyl)methylidene]amino}‐ N ‐(5‐methyl‐1,2‐oxazol‐3‐yl)benzene‐1‐sulfonamide ( L 2 ) were synthesized by the condensation reaction of 4‐aminobenzene‐1‐sulfonamide and 4‐amino‐ N ‐(3‐methyl‐2,3‐dihydro‐1,2‐oxazol‐5‐yl)benzene‐1‐sulfonamide with 2‐hydroxy‐3‐methoxybenzaldehyde in an equimolar ratio. Sulfonamide core ligands behaved as bidentate ligands and coordinated with transition metals via nitrogen of azomethine and the oxygen of the hydroxyl group. Ligand L 1 was recovered in its crystalline form and was analyzed by single‐crystal X‐ray diffraction technique which held monoclinic crystal system with space group ( P 2 1 / c ). The structures of the ligands L 1 and L 2 and their transition metal complexes were established by their physical (melting point, color, yields, solubility, magnetic susceptibility, and conductance measurements), spectral (UV–visible [UV–Vis], Fourier transform infrared spectroscopy, 1 H NMR, 13 C NMR, and mass analysis), and analytical (CHN analysis) techniques. Furthermore, computational analysis (vibrational bands, frontier molecular orbitals (FMOs), and natural bonding orbitals [NBOs]) were performed for ligands through density functional theory utilizing B3LYP/6‐311+G(d,p) level and UV–Vis analysis was carried out by time‐dependent density functional theory. Theoretical spectroscopic data were in line with the experimental spectroscopic data. NBO analysis confirmed the extraordinary stability of the ligands in their conjugative interactions. Global reactivity parameters computed from the FMO energies indicated the ligands were bioactive by nature. These procedures ensured the charge transfer phenomenon for the ligands and reasonable relevance was established with experimental results. The synthesized compounds were screened for antimicrobial activities against bacterial ( Streptococcus aureus , Bacillus subtilis , Eshcheria coli , and Klebsiella pneomoniae ) species and fungal ( Aspergillus niger and Aspergillus flavous ) strains. A further assay was designed for screening of their antioxidant activities (2,2‐diphenyl‐1‐picrylhydrazine radical scavenging activity, total phenolic contents, and total iron reducing power) and enzyme inhibition properties (amylase, protease, acetylcholinesterase, and butyrylcholinesterase). The substantial results of these activities proved the ligands and their transition metal complexes to be bioactive in their nature.
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