A new azo‐Schiff base: Synthesis, characterization, biological activity and theoretical studies of its complexes

Zoubi, Wail Al; Al‐Hamdani, Abbas Ali Salih; Ahmed, Susan Duraid; Ko, Young Gun

doi:10.1002/aoc.3895

Cited by 54 publications

(43 citation statements)

References 42 publications

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“…In the case of [Cu 2 LCl 4 ]Th, [Hg 2 LCl 4 ]Td, [Co 2 LCl 4 ]Td, [Pd 2 LCl 4 ]Sp and [Ni 2 LCl 4 ]Td, bands are attributed to n → π* transition related to C═N bond and M → L charge transfer transition. From the results in Table , the spectra of the metal complexes also show bands at 693, 965, 609, 875, 520, 599, 899, 500, 592 and 489, 590, 745 nm in this case owing to the charge transfer in complexes VO(II), Pt(IV), Pd(II), Co(II) and Ni(II), confirming the absence of any d–d transition . The magnetic value of the metal complexes is in accordance with octahedral geometry for diamagnetic systems.…”

Section: Resultssupporting

confidence: 66%

Phosphorus Schiff base ligand and its complexes: Experimental and theoretical investigations

Suleman

Al‐Hamdani

Ahmed

et al. 2020

Applied Organom Chemis

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A phosphorus‐containing Schiff base was prepared from bis{3‐[2‐(4‐amino‐1,5‐dimethyl‐2‐phenylpyrazol‐3‐ylideneamino)ethyl]indol‐1‐ylmethyl}phosphinic acid and paraformaldehyde as a novel antibacterial compound. The reaction of the Schiff base ligand with VO(IV), Ni(II), Co(II), Cu(II), Zn(II), Cd(II), Hg(II), Pd(II) and Pt(IV) led to binuclear species of metal complexes, depending on the ratio of metal ion and ligand. The ligand and its complexes were investigated using elemental analysis, Fourier transform infrared, 1H NMR, 13C NMR, UV–visible and mass spectra, thermogravimetric analysis, conductivity measurements and thermal analysis. The results showed that the Schiff base behaves as a tetradentate ligand; moreover, on the basis of conductance results, of all the prepared complexes are non‐electrolytes, excepting the Pt(IV) complex. The metal complexes were found to be formed with a metal‐to‐ligand ratio of 2:1, except for the Pt(IV) complex with a ratio of 1:1. The activation thermodynamic parameters (ΔE*, ΔH*, ΔS*, ΔG* and K) and the activation energy of thermal decomposition were determined from thermogravimetric analysis using the Coats–Redfern method. The biological activities of the metal complexes were screened against the growth of bacteria and fungi in vitro to assess the antimicrobial potential and study the toxicity of the compounds. The prepared compounds have noteworthy antimicrobial properties.

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Section: Resultssupporting

confidence: 66%

Phosphorus Schiff base ligand and its complexes: Experimental and theoretical investigations

Suleman

Al‐Hamdani

Ahmed

et al. 2020

Applied Organom Chemis

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“…Prepared compounds showed high inhibition zone against the gram‐positive bacterium S aureus ; moreover, it showed relatively lower activities against the gram‐negative bacterium Salmonella enterica at the highest used concentration (20 mg/mL). Compound showed relatively higher antibacterial activity against the C albicans and C tropicalis ; nevertheless, it has showed relatively lower activity against C tropicalis (Table ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and bioactivity studies of novel Schiff bases and their complexes

Zoubi

Jirjees

Suleman

et al. 2019

J of Physical Organic Chem

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The new Schiff base (L) “4‐[(2,4‐dimethoxy‐benzylidene)‐amino]‐1,5‐dimethyl‐2‐phenyl‐1,2‐dihydro‐pyrazol‐3‐one” was synthesized from 2,4‐dimethoxy‐benzaldehyde and 4‐amino‐1,5‐dimethyl‐2‐phenyl‐1,2‐dihydropyrazol‐3‐one, and the geometry of Schiff base was characterized and determined by proton nuclear magnetic resonance (1H‐NMR), mass, Fourier transform infrared (FT‐IR), and ultraviolet‐visible (UV‐vis) spectroscopy. Schiff complexes of Ni(II), Pd(II), Pt(IV), Zn(II), Cd(II), and Mg(II) have been prepared by reaction of ion metals with as‐prepared Schiff base. The results showed that synthesized complexes offered 1:2 metal‐ligand ratios. Furthermore, the Schiff complexes were a tetrahedral in complexes Ni(II), Zn(II), Cd(II), and Hg(II), octahedral Pt(II), and square planer complex Pd(II). Additionally, density functional theory (DFT) was applied for calculations of both spectroscopic properties and electronic structure of prepared Schiff bases. Moreover, the Schiff base and its metal complexes have been verified in vitro against Streptococcus, Esherichia coli, Candida albicans, and Candida tropicalis in order to assess their antibacterial potential. The findings indicate that the biological activity augments on complexation reaction.

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“…The azo‐derivatives of pyrazolone compounds have attracted attention because of their potential importance in medicinal chemistry as antimicrobial and therapeutic agents, in analytical chemistry as complexing agents having an excellent ability to form chelates with a number of metal cations for the determination of these metal ions spectrophotometrically, and in industrial chemistry as dyestuffs . Metal complexes of these compounds have shown biological activity in comparison to without metals …”

Section: Introductionmentioning

confidence: 99%

New Ni(II), Pd(II) and Pt(II) complexes coordinated to azo pyrazolone ligand with a potent anti‐tumor activity: Synthesis, characterization, DFT and DNA cleavage studies

Bakr

Al‐Hefnawy

Awad

et al. 2017

Applied Organom Chemis

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The absolute necessity to fight some class of tumor is perceived as serious health concerns, so the discovery and development of effective anticancer agents are urgently needed. (E)‐4‐((2‐hydroxyphenyl)diazenyl)‐3‐phenyl‐1H‐pyrazol‐5(4H)‐one, HL, and its Ni(II), Pd(II) and Pt(II) complexes were synthesized and the biological activity was evaluated for antitumor, antioxidant and antimicrobial activity as well as DNA cleavage. Their structures were assigned depending on the elemental analysis, conductivity, magnetic moment, spectral measurements (IR, 1HNMR, mass and UV–Vis) and thermal analysis. 3D molecular modeling using DFT method confirmed that the geometrical structures agree well with the suggested experimental ones. The antitumor activity was evaluated against four different cell lines using MTT assay. The ligand HL showed a potent cytotoxic activity compared to 5‐fluorouracil as a reference drug. For metal complexes, the order of activity was: Pd(II) > Ni(II) > Pt(II). A remarkable antioxidant activity for the ligand HL was recorded. It was higher than that of the metal complexes. Results of antimicrobial experiments revealed that all compounds were moderate to highly active against selected bacterial strains but inactive as antifungal except Pd(II) which showed a moderate antifungal activity. Gel electrophoresis showed insignificant nucleases activity for the ligand or its metal complexes even in the presence of H2O2 providing protection of DNA from damage. The antitumor activity of our compounds may be not due to DNA cleavage but may be referred to a mechanism similar to that of 5‐fluorouracil which interfere with DNA replication. The present work suggests the use of this ligand in the design and development of new anticancer drugs.

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A new azo‐Schiff base: Synthesis, characterization, biological activity and theoretical studies of its complexes

Cited by 54 publications

References 42 publications

Phosphorus Schiff base ligand and its complexes: Experimental and theoretical investigations

Phosphorus Schiff base ligand and its complexes: Experimental and theoretical investigations

Synthesis and bioactivity studies of novel Schiff bases and their complexes

New Ni(II), Pd(II) and Pt(II) complexes coordinated to azo pyrazolone ligand with a potent anti‐tumor activity: Synthesis, characterization, DFT and DNA cleavage studies

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