Antimicrobial metal-based thiophene derived compounds

Yasmeen, Shakeela; Sumrra, Sajjad Hussain; Akram, Muhammad Safwan; Chohan, Zahid H.

doi:10.1080/14756366.2016.1238363

Cited by 31 publications

(14 citation statements)

References 30 publications

(24 reference statements)

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“…650.00) showing its fragment at m/z = 254 to be highly stable (base peak). The other important mass fragments in their increasing abundance (%) were found as 650 (18) (42), and 781 (30). The base peaks of the metal complexes were found to be distinct in their m/z in relation to their ligand.…”

Section: Mass Spectramentioning

confidence: 93%

“…The in vitro antibacterial activity was tested by using the disc diffusion bioassay technique. [ 42 ] All the designed compounds were experienced against the four bacterial pathogens. Among the bacterial strains, two were Gram‐positive ( Staphylococcus aureus and Klebsiella pneumoniae ), whereas the other two were the Gram‐negative ( Escherichia coli and Bacillus subtilis ) strains.…”

Section: Methodsmentioning

confidence: 99%

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Design, facile synthesis, spectroscopic characterization, and medicinal probing of metal‐based new sulfonamide drugs: A theoretical and spectral study

Hassan

Sumrra

Raza

et al. 2020

Applied Organom Chemis

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Sulfonamide core‐based new ligands 4‐{[(2,4‐dihydroxyphenyl)methylidene]amino}benzene‐1‐sulfonamide as (L1) and 4‐[(2,4‐dihydroxyphenyl)methylidene]amino‐N‐(5‐methyl‐1,2‐oxazol‐3‐yl)benzene‐1‐sulfonamide as (L2) have been synthesized through condensation response and were characterized by their UV–Vis, FT‐IR, 1H NMR, 13C NMR, mass spectrometry, and elemental analyses. The ligands were reacted with transition metals (V, Fe, Co, Ni, Cu, and Zn) to synthesize the metal complexes (1)–(12). The metal complexes were also characterized, based on their physical (color, solubility, yield and melting point, conductance, magnetic), spectral (UV–Vis, FT‐IR, LC–MS), and microanalytical (elemental) data. The bidentate ligands were coordinated with transition metal salts by exploiting the azomethine nitrogen and the hydroxyl group oxygen. The electronic spectra for the metal complexes suggested them to have square‐pyramidal geometry for their vanadyl complexes whereas all the remaining complexes to be octahedral. The optimized geometries of the ligands at their ground state energies were studied through density functional approach at the B3LYP/6‐31G** level. The electronic, molecular electrostatic potential (MEP), and chemical descriptive properties were also explored by first‐principle insights. A clear intramolecular charge transfer was witnessed by occupied molecular orbitals (HOMO) to unoccupied molecular orbitals (LUMO). In addition, all the products were then tested for their antimicrobial potential against four bacterial (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Klebsiella pneumoniae) and two fungal (Aspergillus flavus and Aspergillus niger) species. The synthetic products were also tested for their antioxidant and enzyme inhibition properties that gave the excellent results implying their bioactive nature. The screening results revealed the metal complexes to have enhanced bioactive actions in comparison with their respective ligands.

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Section: Mass Spectramentioning

confidence: 93%

Section: Methodsmentioning

confidence: 99%

Design, facile synthesis, spectroscopic characterization, and medicinal probing of metal‐based new sulfonamide drugs: A theoretical and spectral study

Hassan

Sumrra

Raza

et al. 2020

Applied Organom Chemis

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“…Metal complexes were synthesized by taking the ligand to metal ratio as 2:1, adopting the previously reported procedure . The respective metallic salt (50 mmol) was added to a magnetically refluxing (100 mmol) ethanolic solution of the ligand.…”

Section: Methodsmentioning

confidence: 99%

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

Sumrra

Hassan

Imran

et al. 2020

Applied Organom Chemis

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This study reports the synthesis of sulfonamide‐derived Schiff bases as ligands L1 and L2 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 (L1) and 4‐{[(2‐hydroxy‐3‐methoxyphenyl)methylidene]amino}‐N‐(5‐methyl‐1,2‐oxazol‐3‐yl)benzene‐1‐sulfonamide (L2) 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 L1 was recovered in its crystalline form and was analyzed by single‐crystal X‐ray diffraction technique which held monoclinic crystal system with space group (P21/c). The structures of the ligands L1and L2 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, 1H NMR, 13C 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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“…The antibacterial activity of free ligand and its metal complexes was tested in vitro against the bacterial species Staphylococcus aureus, Streptococcus mutans , Klebsiella pneumonia, and Pseudomonas aeroginosa by the agar well diffusion method using streptomycin as reference. The screening was carried out according to a method reported in the literature . The plates were incubated at 37°C for 24 h. The antibacterial activity was assayed by measuring the diameter of the inhibition zone formed around the well.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Evaluation of some 3d Metal Complexes with a Novel Heterocyclic Schiff Base

Thomas

Mohanan

2017

J Chinese Chemical Soc

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A heterocyclic Schiff base was prepared by condensing 3‐acetylcoumarin with 2‐amino‐3‐carboxyethyl‐4,5,6,7‐tetrahydrobenzo[b]thiophene. Such Schiff bases derived from two different heterocyclic moieties are rare and expected to have properties surpassing those of either of the parent compounds in effectiveness of complex formation and biological activities. This ligand formed a series of complexes with manganese(II), cobalt(II), nickel(II), copper(II), and zinc(II) ions. The ligand and the metal complexes were characterized by various physicochemical and spectral studies. These included elemental analysis, molar conductance, magnetic susceptibility, as well as UV–vis, IR, 1H NMR, 13C NMR, and ESR spectral studies. The ESR spectral data adequately supported the covalent nature of the metal–ligand bonds. The ligand possessed a hexagonal crystal structure, but on complexation the crystallinity was lost. The fluorescence spectra of the ligand and its metal complexes in DMSO were also recorded. The ligand and the metal complexes were screened for their antimicrobial activities, and it was observed that the metal complexes are more active than the ligand. The α‐amylase inhibitory activity and the DNA cleavage activity of the ligand and the metal complexes were also examined. in vitro antitumor activity of the copper(II) complex was assayed against human cervical carcinoma cells (HeLa cell line), showing that the complex exhibited promising antitumor activity on the HeLa cell line.

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Antimicrobial metal-based thiophene derived compounds

Cited by 31 publications

References 30 publications

Design, facile synthesis, spectroscopic characterization, and medicinal probing of metal‐based new sulfonamide drugs: A theoretical and spectral study

Design, facile synthesis, spectroscopic characterization, and medicinal probing of metal‐based new sulfonamide drugs: A theoretical and spectral study

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

Synthesis and Biological Evaluation of some 3d Metal Complexes with a Novel Heterocyclic Schiff Base

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