Nano-Azo Ligand and Its Superhydrophobic Complexes: Synthesis, Characterization, DFT, Contact Angle, Molecular Docking, and Antimicrobial Studies

Metal complexes of the 2,2'-(1,3-phenylenebis(diazene-2,1-diyl))bis(4-aminobenzoic acid) diazo ligand (H2L) derived from m-phenylenediamine and p-aminobenzoic acid were synthesized and characterized by different spectral, thermal, and analytical tools. The H2L ligand reacted with the metal ions Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) as 1 : 1 stoichiometry. All complexes displayed an octahedral geometry according to the electronic and magnetic moment measurements. The IR spectra revealed the binding of the azo ligand to the metal ions via two azo nitrogen atoms and protonated carboxylate O in a neutral tetradentate manner. Both IR and 1H NMR spectra documented the involvement of the carboxylate group without proton displacement. The thermal studies pointed out that the complexes had higher thermal stability comparable with that of the free ligand. SEM images revealed the presence of the diazo ligand and its Cd(II) complex in a nanostructure form. The contact angle measurements proved that the Cd(II) complex can be considered as a superhydrophobic material. The molecular and electronic structure of H2L and [Cd(H2L)Cl2].H2O were optimized theoretically, and the quantum chemical parameters were calculated. The biological activities of the ligand, as well as its metal complexes, have been tested in vitro against some bacteria and fungi species. The results showed that all the tested compounds have significant biological activities with different sensitivity levels. The binding between H2L and its Cd(II) complex with receptors of the crystal structure of S. aureus (PDB ID: 3Q8U), crystal structure of protein phosphatase (PPZ1) of Candida albicans (PDB ID: 5JPE), receptors of breast cancer mutant oxidoreductase (PDB ID: 3HB5), and crystal structure of Escherichia coli (PDB ID: 3T88) was predicted and given in detail using molecular docking.

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Synthesis, Characterization and in vitro Biological Evaluation of a New Schiff Base Derived from Drug and its Complexes with Transition Metal Ions

Revista de Chimie ◽

10.37358/rc.18.7.6393 ◽

2018 ◽

Vol 69 (7) ◽

pp. 1678-1681

Author(s):

Amina Mumtaz ◽

Tariq Mahmud ◽

M. R. J. Elsegood ◽

G. W. Weaver

Keyword(s):

Schiff Base ◽

Transition Metal ◽

Metal Ions ◽

Metal Complexes ◽

Transition Metal Complexes ◽

Free Ligand ◽

Transition Metal Ions ◽

Biological Evaluation ◽

Pyridoxal Hydrochloride

New series of copper (II), cobalt (II), zinc (II), nickel (II), manganese (II), iron (II) complexes of a novel Schiff base were prepared by the condensation of sulphadizine and pyridoxal hydrochloride. The ligand and metal complexes were characterized by utilizing different instrumental procedures like microanalysis, thermogravimetric examination and spectroscopy. The integrated ligand and transition metal complexes were screened against various bacteria and fungus. The studies demonstrated the enhanced activity of metal complexes against reported microbes when compared with free ligand.

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Utilization and simulation of innovative new binuclear Co(ii), Ni(ii), Cu(ii), and Zn(ii) diimine Schiff base complexes in sterilization and coronavirus resistance (Covid-19)

Open Chemistry ◽

10.1515/chem-2021-0068 ◽

2021 ◽

Vol 19 (1) ◽

pp. 772-784

Author(s):

Moamen S. Refat ◽

Ahmed Gaber ◽

Walaa F. Alsanie ◽

Mohamed I. Kobeasy ◽

Rozan Zakaria ◽

...

Keyword(s):

Schiff Base ◽

Molecular Docking ◽

Metal Ions ◽

Free Ligand ◽

Schiff Base Complexes ◽

Hydroxyl Groups ◽

Binuclear Complexes ◽

Central Metal ◽

H Nmr ◽

Biological Studies

Abstract This article aimed at the synthesis and molecular docking assessment of new diimine Schiff base ligand, namely 2-((E)-(2-((Z)-2-(4-chlorophenyl)-2-hydroxyvinyl)hydrazono) methyl)-6-methoxyphenol (methoxy-diim), via the condensation of 1-(4-chloro-phenyl)-2-hydrazino-ethenol compound with 2-((E)-(2-((Z)-2-(4-chlorophenyl)-2-hydroxy vinyl) hydrazono)methyl)-6-methoxyphenol in acetic acid as well as the preparation of new binuclear complexes of Co(ii), Ni(ii), Cu(ii), and Zn(ii). The following synthesized complexes were prepared in a ratio of 2:1 (metal/ligand). The 1H-NMR, UV-Vis, and FTIR spectroscopic data; molar conductivity measurements; and microanalytical, XRD, TGA/DTG, and biological studies were carried out to determine the molecular structure of these complexes. According to the spectroscopic analysis, the two central metal ions were coordinated with the diamine ligand via the nitrogen of the hydrazine and oxygen of the hydroxyl groups for the first metal ions and via the nitrogen of the hydrazine and oxygen of the phenol group for the second metal ions. Molecular docking for the free ligand was carried out against the breast cancer 3hb5-oxidoreductase and the 4o1v-protein binding kidney cancer and COVID-19 protease, and good results were obtained.

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Synthesis, Characterization, Crystal Structure, and Biological Activities of Transition Metal Complexes with 1-Phenyl-3-methyl-5-hydroxypyrazole-4-methylene-8′-quinolineimine

Zeitschrift für anorganische und allgemeine Chemie ◽

10.1002/zaac.201200475 ◽

2013 ◽

Vol 639 (5) ◽

pp. 832-841 ◽

Cited By ~ 8

Author(s):

Xiao-Ying Cheng ◽

Ming-Fang Wang ◽

Zheng-Yin Yang ◽

Yong Li ◽

Zeng-Chen Liu ◽

...

Keyword(s):

Crystal Structure ◽

Transition Metal ◽

Metal Complexes ◽

Transition Metal Complexes ◽

Biological Activities

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Synthesis, Characterization, Molecular Docking and Enzyme Inhibition Studies of Some Novel Enaminone Derivatives and Their Complexes with Cu(II), Cd(II) and Co(II) Ions

Revista de Chimie ◽

10.37358/rc.19.10.7597 ◽

2019 ◽

Vol 70 (10) ◽

pp. 3564-3569

Author(s):

Rahila Huma ◽

Tariq Mahmud ◽

Liviu Mitu ◽

Muhammad Ashraf ◽

Ambar Iqbal ◽

...

Keyword(s):

Molecular Docking ◽

Transition Metal ◽

Metal Ions ◽

Metal Complexes ◽

1H Nmr ◽

13C Nmr ◽

Transition Metal Ions ◽

Binding Mode ◽

Inhibitory Activities ◽

Inhibition Studies

Two new enaminone ligands, 3-chloro-4-{(4-chlorophenyl)amino}pent-3-en-2-one (Ac-PCA), 4-(benzylamino)-3-chloropent-3-en-2-one (Ac-BA) and their metal complexes with transition metal ions [Cu(II), Cd(II) and Co(II)] were prepared and subsequently characterized by FTIR, ICP-AES, UV-Vis, TGA, 1H NMR, 13C NMR and FAB-MS. These newly synthesized compounds were further investigated for anti-acetylcholinesterase (AChE) and anti-urease activities. The (Ac-BA)Cu(II) complex exhibited good anti-AChE while (Ac-BA)2Co(II) complex was potent against anti-urease activities. Other ligands and complexes showed poor to no enzyme inhibitory activities. The synthesized compounds were docked inside acetylcholinesterase enzymes to determine their putative binding mode.

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Synthesis, spectral characterization and biological activities of Ag(I), Pt(IV) and Au(III) complexes with novel azo dye ligand (N,N,O) derived from 2-amino-6-methoxy benzothiazole

10.21203/rs.3.rs-953144/v1 ◽

2022 ◽

Author(s):

Hussein A. K. Kyhoiesh ◽

Khalid J. Al-Adilee

Keyword(s):

Crystal Structure ◽

Endometrial Cancer ◽

Nitrogen Atom ◽

Metal Complexes ◽

Cancer Cells ◽

Azo Dye ◽

Biological Activities ◽

Antifungal Drugs ◽

Azo Compounds ◽

Spectroscopic Techniques

Abstract The novel ligand 2-[2'-(6-methoxybenzothiazolyl)azo]-3,5-dimethyl benzoic acid (6-MBTAMB), derived from 2-amino-6-methoxy benzothiazole, has been used to synthesize a series of new metal complexes of Ag(I), Pt(IV) and Au(III). The metal complexes were characterized by elemental analyses (CHNS), molar conductivity, crystal structure (XRD), spectroscopic techniques: FT-IR, 1H NMR, 13C NMR, UV-Vis, mass spectra, thermal analysis (TG-DTA), FE-SEM and magnetic properties. Results confirmed that the azo dye ligand behaves a tridentate and coordinates to the metal ion via nitrogen atom of azomethine group of heterocyclic benzothiazole ring, nitrogen atom of the azo group which is the farthest of the benzothiazole molecule and carboxylic oxygen. Antimicrobial properties of all newly synthesized azo compounds are also demonstrated against bacterial pathogenic organisms and fungi. These complexes are more effective against bacteria and less effective against fungi compared to standard antibacterial drugs (Novobiocin) and antifungal drugs (Cycloheximide). By using the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging test, it was discovered that the complexes had good antioxidant properties. In addition, the (6-MBTAMB) and metal complexes were docked with the crystal structure of FGF Receptor 2 (FGFR2) kinase domain harboring the pathogenic gain of function K659E mutation identified in endometrial cancer using the Molecular Operating Environment module (MOE). In vitro studies on human endometrial cancer cell lines (MFE-296) as well as healthy human umbilical vein endothelial cells (HUVEC) show uptake of the intact compounds by the cancer cells and increased activity against the cancer cells.

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Synthesis and Characterization of Bioactive Acylpyrazolone Sulfanilamides and Their Transition Metal Complexes: Single Crystal Structure of 4-Benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one Sulfanilamide

Bioinorganic Chemistry and Applications ◽

10.1155/2015/717089 ◽

2015 ◽

Vol 2015 ◽

pp. 1-14 ◽

Cited By ~ 8

Author(s):

Omoruyi G. Idemudia ◽

Alexander P. Sadimenko ◽

Anthony J. Afolayan ◽

Eric C. Hosten

Keyword(s):

Crystal Structure ◽

Schiff Base ◽

Transition Metal ◽

Metal Complexes ◽

Single Crystal ◽

Transition Metal Complexes ◽

Antimicrobial Agents ◽

Biological Activities ◽

Condensation Reaction ◽

Single Crystal Structure

Two Schiff base ligands Ampp-Sn1and Bmpp-Sn2, afforded by a condensation reaction between sulfanilamide and the respective acylpyrazolone carbonyl precursors, their Mn(II), Co(II), Ni(II), and Cu(II) complexes prepared by the reaction of ligands and corresponding metal salts in aqueous solutions, were synthesized and then characterized by both analytical and spectroscopic methods, in a view to developing new improved bioactive materials with novel properties. On the basis of elemental analysis, spectroscopic and TGA results, transition metal complexes, with octahedral geometry having two molecules of the bidentate keto-imine ligand each, have been proposed. The single crystal structure of Bmpp-Sn according to X-ray crystallography showed a keto-imine tautomer type of Schiff base, having three intramolecular bonds, one short N2⋯H2⋯O3 hydrogen bond of 1.90 Å and two long C13⋯H13⋯O2 and C32⋯H32⋯O3 hydrogen bonds of 2.48 Å. A moderate to low biological activities have been exhibited by synthesized compounds when compared with standard antimicrobial agents on screening the synthesized compounds againstStaphylococcus aureus,Bacillus pumilus,Proteus vulgaris, andAeromonas hydrophilafor antibacterial activity and against free radical 1, 1-diphenyl-2-picryl-hydrazyl (DPPH) for antioxidant activity.

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