Design, synthesis, antimicrobial and antioxidant activity of 3-formyl chromone hydrazone and their metal (II) complexes

Philip, Jessica Elizabeth; Antony, Shanty Angamaly; Eeettinilkunnathil, Sneha Jose; Kurup, M.R. Prathapachandra; Velayudhan, Mohanan Puzhavoorparambil

doi:10.1016/j.ica.2017.09.006

Cited by 36 publications

(16 citation statements)

References 34 publications

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“…There is a continuous interest in synthesis of chromones and chromone‐based ligands and their complexes because of variable applications of these compounds, namely, antimicrobial, [ 9 ] antitumor, [ 10 ] antiplasmodial and anti‐inflammatory, [ 11 ] antioxidant, [ 12 ] and anti‐Alzheimer [ 13 ] properties as well as other biological and pharmaceutical applications. [ 14 ]…”

Section: Introductionmentioning

confidence: 99%

Coordinating behavior of hydrazone ligand bearing chromone moiety towards Cu(II) ions: Synthesis, spectral, density functional theory (DFT) calculations, antitumor, and docking studies

Abdelrhman

El‐Shetary

Adly

2021

Applied Organom Chemis

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A new hydrazone ligand (FCSH; HL) was successfully synthesized by the reaction of salicylaldehyde hydrazone with 3‐formylchromone. Seven copper(II) hydrazone complexes have been synthesized by using several copper(II) salts (acetate, nitrate, sulfate, perchlorate, chloride, and bromide). Elemental analysis, electronic, infrared, mass, nuclear magnetic resonance, electron spin resonance spectra, thermal analysis, molar conductivity, and magnetic susceptibility measurements were used to characterize structures of the hydrazone ligand and its complexes. The ligand behaves as monobasic tridentate for all complexes except complex 2 (monobasic tetradentate) and complex 4 (neutral tridentate). All metal complexes exhibited octahedral geometries. With the aid of Coats–Redfern equations, the kinetic parameters (Ea, A, ∆H, ∆S, and ∆G) of the thermal decomposition stages were calculated and discussed. At the B3LYP/6‐311G(d,p) level engaged in the Gaussian 09 program, density functional theory (DFT) calculations were carried out to inspect the optimized structures of the chelating agent and its complexes. The hydrazone ligand and its copper(II) complexes showed antitumor activity towards HepG2 cell line. The docking study of the hydrazone ligand and its copper(II) complexes was investigated with the active site of the CDK2 kinase.

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Section: Introductionmentioning

confidence: 99%

Coordinating behavior of hydrazone ligand bearing chromone moiety towards Cu(II) ions: Synthesis, spectral, density functional theory (DFT) calculations, antitumor, and docking studies

Abdelrhman

El‐Shetary

Adly

2021

Applied Organom Chemis

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“…The derivatives of quinoline and hydrazone constitute significant categories of compounds that have found multiple applications in therapeutic chemistry because of their wide range of pharmacokinetic properties, [ 1–3 ] especially their prominence in drug discovery programs. [ 4,5 ] The derivatives of quinoline and hydrazone and their complexes have been reported to demonstrate a widespread spectrum of biological properties, [ 6–8 ] such as antimicrobial, [ 9–11 ] antibacterial, [ 12–14 ] antifungal, [ 15,16 ] antiviral, [ 17 ] antiplatelet [ 18 ] antimalarial, [ 19 ] antitubercular, antimycobacterial, [ 20,21 ] anticancer, [ 21–24 ] antianalgesic, anticonvulsant, [ 25 ] and antileishmanial, [ 26,27 ] The hydrazones and their metal complexes also have anti‐uropathogenic, [ 28 ] anti‐arthritic, [ 29 ] antiproliferative, [ 30 ] and antioxidant [ 31–33 ] properties and act as inhibitors for COX‐2, [ 22 ] potent antiangiogenic agents in atherosclerosis, [ 31 ] and potent immunomodulatory agents. [ 34 ] They play a role in the treatment of Alzheimer's disease [ 35,36 ] and inhibit the corrosion of mild steel in acidic media.…”

Section: Introductionmentioning

confidence: 99%

Transition metal complexes derived fromN′‐(4‐fluorobenzylidene)‐2‐(quinolin‐2‐yloxy) acetohydrazide: Synthesis, structural characterization, and biocidal evaluation

El‐Saied

Shakdofa

Al‐Hakimi

et al. 2020

Applied Organom Chemis

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complexes of a synthetic novel hydrazone containing a quinoline moiety were prepared. The composition and structure of the prepared compounds were elucidated by spectral and analytical techniques. The results reveal that all complexes were formed in 1:1 mole ratio except Mn 2+ and Cu 2+ complexes (3) and (7), which were formed in 1 M:2 L mole ratio. It was also found that the ligand binds the metal ions via NO donor sites as a monobasic bidentate chelator in all complexes through the enolic carbonyl oxygen and azomethine nitrogen atoms. The electronic absorption spectra and magnetic moment data demonstrated square pyramidal and octahedral geometries for the VO 2+ and Ni 2+ complexes, respectively, while the other complexes adopted tetrahedral geometry. The thermal decomposition of the complexes was discussed in relation to structure. The thermal analysis data demonstrated that all complexes were decomposed in one, two, three or four stages starting with the dehydration process, removal of coordination water molecules or elimination of anions and ended with the formation of the metal oxide. The bactericidal activities of the prepared compounds demonstrated that hydrazone (1) exerted a highly inhibitory effect against B. subtilis while VO 2+ , Co 2+ , and Cu 2+ complexes (2), (4), and (7) showed an inhibitory effect against E. coli more than the tetracycline. Additionally, the inhibitory effect of the prepared compound against A. niger showed that the Cu 2+ complex (6) is the most active while the Ni 2+ , Cu 2+ , and Zn 2+ complexes (5-8) exhibited an extremely inhibitory effect against C. albicans.

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“…Examples of the Ag-containing compounds synthesized include those containing camphorimines, tetraazoles, albendazoles or phenantrolines as ligands (Table 5) [145][146][147][148]. Complexes with other metal centers like copper, cobalt, nickel or iron; or even with metals not usually used as bioagents, such as tin, chromium, cadmium or lead [149][150][151][152][153][154][155][156][157], have also been synthesized and shown to display moderate anti C. albicans activity ( Table 5). Polinuclear complexes (based on Cu, Cd or Ni), particularly those harbouring ferrocenyl derived ligands, were also reported to have high activity against C. albicans (Table 5) [158].…”

Section: New Compounds Obtained By Chemical Synthesismentioning

confidence: 99%

An Overview on Conventional and Non-Conventional Therapeutic Approaches for the Treatment of Candidiasis and Underlying Resistance Mechanisms in Clinical Strains

Salazar

Simões

Pedro

et al. 2020

JoF

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Fungal infections and, in particular, those caused by species of the Candida genus, are growing at an alarming rate and have high associated rates of mortality and morbidity. These infections, generally referred as candidiasis, range from common superficial rushes caused by an overgrowth of the yeasts in mucosal surfaces to life-threatening disseminated mycoses. The success of currently used antifungal drugs to treat candidiasis is being endangered by the continuous emergence of resistant strains, specially among non-albicans Candida species. In this review article, the mechanisms of action of currently used antifungals, with emphasis on the mechanisms of resistance reported in clinical isolates, are reviewed. Novel approaches being taken to successfully inhibit growth of pathogenic Candida species, in particular those based on the exploration of natural or synthetic chemicals or on the activity of live probiotics, are also reviewed. It is expected that these novel approaches, either used alone or in combination with traditional antifungals, may contribute to foster the identification of novel anti-Candida therapies.

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Design, synthesis, antimicrobial and antioxidant activity of 3-formyl chromone hydrazone and their metal (II) complexes

Cited by 36 publications

References 34 publications

Coordinating behavior of hydrazone ligand bearing chromone moiety towards Cu(II) ions: Synthesis, spectral, density functional theory (DFT) calculations, antitumor, and docking studies

Coordinating behavior of hydrazone ligand bearing chromone moiety towards Cu(II) ions: Synthesis, spectral, density functional theory (DFT) calculations, antitumor, and docking studies

Transition metal complexes derived fromN′‐(4‐fluorobenzylidene)‐2‐(quinolin‐2‐yloxy) acetohydrazide: Synthesis, structural characterization, and biocidal evaluation

An Overview on Conventional and Non-Conventional Therapeutic Approaches for the Treatment of Candidiasis and Underlying Resistance Mechanisms in Clinical Strains

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