Crystal structure, optical properties, DFT analysis of new morpholine based Schiff base ligands and their copper(II) complexes: DNA, protein docking analyses, antibacterial study and anticancer evaluation

Dhahagani, K.; Kesavan, Mookkandi Palsamy; Vinoth, Kumar Gujuluva Gangatharan; Ravi, Lokesh; Rajagopal, Gurusamy; Rajesh, Jegathalaprathaban

doi:10.1016/j.msec.2018.04.032

Cited by 58 publications

(14 citation statements)

References 36 publications

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“…In this regard, the Schiff bases and their metal complexes play an important role in the bioinorganic chemistry due to their structural diversity and wide spectrum of their biological activities. A number of copper and silver complexes with Schiff bases have been already studied for antibacterial activity [4][5][6][7][8][9][10][11][12][13][14]. Actually, there is not a drug that incorporates a copper in their structure, but is available only one product with silver, silver sulfadiazine (SSD).…”

Section: Introductionmentioning

confidence: 99%

Silver(I) and copper(I) complexes with a Schiff base derived from 2-aminofluorene with promising antibacterial activity

Cifuentes-Vaca

Andrades-Lagos

Campanini-Salinas

et al. 2019

Inorganica Chimica Acta

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By reaction of 2-aminofluorene with 2-pyridinecarboxaldehyde a new Schiff base (L) is obtained. The reaction of this ligand with Ag(I) and Cu(I) salts in different stoichiometry leads to the complexes [Ag(CF 3 SO 3)(L)PPh 3 ] (1) or [ML 2 ]A (M = Ag, Cu; A = CF 3 SO 3 , ClO 4 or BF 4). Structural characterization by X-ray crystallography has been carried out for complexes [AgL 2 ]ClO 4 (4) and [Ag(L)(PPh 3) 2 ](CF 3 SO 3) (6), which confirms the chelate nature of L and the presence of Ag•••H interactions between two molecules. The biological studies show that Schiff base L presents antibacterial activity in Gram-positive bacteria and E. coli. The coordination to silver increases this activity, but the formation of the copper complex does not generate significant changes. Highlights 1. The synthesis of a new Schiff base with fluorene is described. 2. Coordination to silver and copper complexes has been carried out

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Section: Introductionmentioning

confidence: 99%

Silver(I) and copper(I) complexes with a Schiff base derived from 2-aminofluorene with promising antibacterial activity

Cifuentes-Vaca

Andrades-Lagos

Campanini-Salinas

et al. 2019

Inorganica Chimica Acta

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“…Computational studies: In this study, the 3D structure of the macrocyclic Schiff base ligands and their Co(II)/Cu(II) complexes are optimized using density functional theory (DFT) calculations were carried out by (B3LYP/6-31G/SDD/ LANL2DZ) basis set with Gaussian 09W program (Figs. 9-11) by using a selection of unrestricted modern density functional [27][28][29]. The basis set 6-31G was used for the N, C and H atoms and LANL2DZ was applied for the Co(II)/Cu(II) ion respectively [30].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization and DFT Studies of Some Co(II) and Cu(II) Complexes of 12-Membered Tetradentate [N4] Macrocyclic Schiff Base Derived from 9,10-Phenanthrenequinone

et al. 2019

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The structures of some coordination compounds of cobalt(II) and copper(II) with macrocyclic Schiff bases obtained by the reaction of 9,10-phenanthrenequinone with diamines synthesized in 1:1 molar ratio(s) have been elucidated by various physico-chemical methods viz. elemental analysis, IR, UV-visible, mass, ESR. The surface morphology was determined by SEM analysis. Infrared spectra suggested that ligand was coordinated to the metal ion in a tetradentate manner through azomethine nitrogen atom by the change in its stretching frequency. ESR spectra of copper(II) complexes indicates the presence of unpaired electron in the dx2–y2 by calculating the g values. The optimized geometries which were calculated using the DFT/B3LYP method were compared with the molecular geometries obtained experimentally.

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“…Computational studies were performed using Gaussian 09 software . UV–Vis analysis was done by B3LYP/6‐311+G(d,p) approximation in the gas phase.…”

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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Crystal structure, optical properties, DFT analysis of new morpholine based Schiff base ligands and their copper(II) complexes: DNA, protein docking analyses, antibacterial study and anticancer evaluation

Cited by 58 publications

References 36 publications

Silver(I) and copper(I) complexes with a Schiff base derived from 2-aminofluorene with promising antibacterial activity

Silver(I) and copper(I) complexes with a Schiff base derived from 2-aminofluorene with promising antibacterial activity

Synthesis, Characterization and DFT Studies of Some Co(II) and Cu(II) Complexes of 12-Membered Tetradentate [N4] Macrocyclic Schiff Base Derived from 9,10-Phenanthrenequinone

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

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