Metal-based ethanolamine-derived compounds: a note on their synthesis, characterization and bioactivity

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

doi:10.1080/14756366.2016.1220375

Cited by 27 publications

(18 citation statements)

References 40 publications

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“…Magnetic susceptibilities are a very useful technique for determining the stereochemistry of metal ions in complexes . They also provide essential information about the number of unpaired electrons, leading to the determination of the geometry of complexes .…”

Section: Resultsmentioning

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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Section: Resultsmentioning

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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“…The absence of ν (OH) band near 3350 cm −1 in the complex further implies the deprotonation and coordination of metal ions to oxygen atoms. [ 22 ] The δ (NH) band at 1606 cm −1 and δ (CH) band at 1487 cm −1 are blueshifted compared to that of ethanolamine, due to the change of chemical structure by coordination reaction with metal ions. Furthermore, the bands at 534 and 470 cm −1 are assigned to ν (CuO) and ν (CuN), confirming the mode of coordination predicted by the DFT simulation.…”

Section: Methodsmentioning

confidence: 99%

A Moisture‐Hungry Copper Complex Harvesting Air Moisture for Potable Water and Autonomous Urban Agriculture

Yang

Zhang

et al. 2020

Advanced Materials

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The earth's atmosphere houses an enormous amount of water, which could be effectively exploited for a plethora of applications. While the development of materials for harnessing this abundant resource has gained impetus in recent years, limited efforts have been devoted to in‐depth research on their agricultural applications. Herein, a novel copper(II)–ethanolamine complex (Cu‐complex), which has a maximum water uptake of up to 300% and a water production rate of 2.24 g g−1 h−1 under natural sunlight, is reported. As a proof‐of‐concept application, using this material, a fully automated and self‐sustainable solar‐powered SmartFarm device is developed. The Cu‐complex harvests atmospheric water during the night, stores the adsorbed water within, and efficiently releases the adsorbed water during the day when the device is exposed to sunlight. The water harvesting and irrigation process can be fine‐tuned to suit different types of plants and local climates for an optimal cultivation. With the SmartFarm in operation, the demand for freshwater for irrigation could be greatly reduced and urban farming techniques such as large‐scale rooftop farming could be promoted with a view of alleviating both water and food scarcity in the near future.

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“…Schiff bases are known to possess potential applications in biological modeling, catalysis, design of molecular magnets, and the synthesis of therapeutic agents [1][2][3][4]. Schiff bases have also been shown to exhibit a broad range of biological activities, including antifungal, antibacterial, antioxidant, and anti-inflammatory properties [4][5][6][7][8][9]. e common structural feature of Schiff's bases is the presence of the characteristic azomethine functionality, RHC � NR′, which has been shown to account for the observed pharmacological activities [4].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Cyclic Voltammetry, and Biological Studies of Co(II), Ni(II), and Cu(II) Complexes of a Tridentate Schiff Base, 1-((E)-(2-Mercaptophenylimino) Methyl) Naphthalen-2-ol (H2L1)

Kuate

Conde

Mainsah

et al. 2020

Journal of Chemistry

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A novel tridentate Schiff base, 1-((E)-(2-mercaptophenylimino) methyl) naphthalen-2-ol (H2L1), was synthesized by the condensation reaction of 2-hydroxy-1-naphthaldehyde with 2-aminothiophenol in absolute ethanol. The resulting ligand was reacted with Co(II), Ni(II), and Cu(II) ions to obtain tetrahedral CoL1, NiL1, and square planar CuL1 complexes. The Schiff base and its metal complexes were characterized using 1H-NMR, microanalysis, FT-IR, UV-visible, and mass spectroscopy (ESI-MS). All the compounds are soluble in DMSO and DMF. Spectroscopic studies show that the ligand coordinates to the metal center through the azomethine nitrogen, naphthoxide oxygen, and thiophenoxide sulfur to form a tridentate chelate system. Conductance measurements show that these compounds are molecular in solution. Cyclic voltammetry studies show Co(III)/Co(II) and Cu(II)/Cu(I) redox systems to be quasi-reversible involving a monoelectronic transfer while Ni(III)/Ni(II) was irreversible. In vitro antibacterial and antifungal activity against five bacterial strains (Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Enterococcus faecalis, and Proteus mirabilis) and five fungal strains (Candida albicans, Candida glabrata, Candida tropicalis, Candida krusei, and Candida parapsilosis) showed no antifungal activity but moderate antibacterial activity on E. coli, S. aureus, P. aeruginosa, and P. mirabilis bacterial strains. Antioxidant studies reveal that the ligand and its Cu(II) complex are more potent than Co(II) and Ni(II) complexes to eliminate free radicals.

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Metal-based ethanolamine-derived compounds: a note on their synthesis, characterization and bioactivity

Cited by 27 publications

References 40 publications

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

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

A Moisture‐Hungry Copper Complex Harvesting Air Moisture for Potable Water and Autonomous Urban Agriculture

Synthesis, Characterization, Cyclic Voltammetry, and Biological Studies of Co(II), Ni(II), and Cu(II) Complexes of a Tridentate Schiff Base, 1-((E)-(2-Mercaptophenylimino) Methyl) Naphthalen-2-ol (H2L1)

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