Synthesis, biological activity, and mechanism of action of new 2-pyrimidinyl hydrazone and N-acylhydrazone derivatives, a potent and new classes of antileishmanial agents

Coimbra, Elaine Soares; Souza, Marcus V. N. de; Terror, Mariana Sequetto; Pinheiro, Alessandra C.; Granato, Juliana da Trindade

doi:10.1016/j.ejmech.2019.111742

Cited by 34 publications

(25 citation statements)

References 45 publications

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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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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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“…[ 19 ] However, for less nucleophilic acyl hydrazides [ 20 ] a catalyst is desirable to conduct the reaction under mild conditions. Thus, in a typical procedure, acyl hydrazide–aldehyde condensation proceeds either in the absence of any catalyst (20–82 °C; 0.33–24 h), [ 21 ] or in the presence of catalytic amount of a Brønsted acid (HCl, 20 °C, 1–72 h; [ 22 ] or AcOH, 82 °C, 12–24 h [ 23 ] ). Tetrabromomethane has never been applied to enhance this condensation and, after preliminary experiments when we established its activity, our idea was to verify the potential and/or limitations of CBr 4 functioning as an organic catalyst in the Schiff reaction.…”

Section: Resultsmentioning

confidence: 99%

Tetrabromomethane as an Organic Catalyst: a Kinetic Study of CBr₄‐Catalyzed Schiff Condensation

et al. 2020

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Tetrabromomethane functions as an organic catalyst for non‐redox reactions of carbonyl species and, in particular, it enhances the aldehyde–acyl hydrazide condensation to give N‐acyl hydrazones. This simple, inexpensive, and commercially available halomethane provides up to 14‐fold acceleration of the Schiff reaction; the kinetic data indicate that the studied condensation exhibits the first order on CBr4. The catalytic activity of CBr4 is significantly higher than the activity of other halogen‐containing species, such as CHX3 or ArX (X = Cl, Br, I).

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“…In to the little cold acting as food agar ways things are done (made a little cold at 40 o c) a special amount of the microbial a hanging (incolumn) was came down hard and mixed completely [44,45]. In the petri plates about 20 ml of this a hanging was comecome down hard aseptically and self-controlled, quiet till the solidification [ 46,47].…”

Section: Preparation Of Inoculumsmentioning

confidence: 99%

Design and synthesis of anti-convulsant and anti-bacterial activity of new hydrazone derivatives

2020

Biointerface Res Appl Chem

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Synthesis of new hydrazone derivatives, starting from 2-(3, 4-Dichloro-benzoyl)-benzoic acid to 2-(3, 4-dichloro-benzoyl) - benzoic acid ethyl ester than converted into 2- (3, 4-Dichloro-benzoyl)-benzoic acid hydrazide with a substituted aldehyde. The structure of newly synthesized compounds was confirmed by analytical and spectral analysis IR, 1HNMR and MASS. For docking study, we took structures of ligand compounds (i.e. AK-series Compounds) and target protein structures into ‘pdb’ file format. Three compounds as possible anti-convulsant AK-1, AK-2 &Ak-4 were considered for compounds Ak-1 was not found suitable for anti-convulsant activity; while AK-2 & AK-4 have the capacity to show anti-convulsant activity with lesser affinity than controls. As an overall conclusion, except Ak-1, other compounds can be further used for anti- convulsant activity. Anti-convulsant activities were performed on rats by using maximal Electroshock Seizure test and minimal Neurotoxicity. Compound 2- (3, 4 – Dichloro-benzoyl)-benzoic acid (4- chloro-benzylidene) (AK-2) shows good anti-convulsant activity. The in-vitro antibacterial strains Escherichia coli MTCC 1573), and staphylococcus aureus (MTCC 1430), were used. Compound 2-(3, 4-Dichloro-benzoyl)-benzoic acid (2-notro-benzylidene-hydrazide (AK-1) gives the highest activity against Escherichia coli (MTCC 1573) and Staphylococcus aureus (MTCC-1430).

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Synthesis, biological activity, and mechanism of action of new 2-pyrimidinyl hydrazone and N-acylhydrazone derivatives, a potent and new classes of antileishmanial agents

Cited by 34 publications

References 45 publications

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

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

Tetrabromomethane as an Organic Catalyst: a Kinetic Study of CBr₄‐Catalyzed Schiff Condensation

Design and synthesis of anti-convulsant and anti-bacterial activity of new hydrazone derivatives

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Synthesis, biological activity, and mechanism of action of new 2-pyrimidinyl hydrazone and N-acylhydrazone derivatives, a potent and new classes of antileishmanial agents

Cited by 34 publications

References 45 publications

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

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

Tetrabromomethane as an Organic Catalyst: a Kinetic Study of CBr4‐Catalyzed Schiff Condensation

Design and synthesis of anti-convulsant and anti-bacterial activity of new hydrazone derivatives

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Tetrabromomethane as an Organic Catalyst: a Kinetic Study of CBr₄‐Catalyzed Schiff Condensation