Facile synthesis, antimicrobial evaluation and molecular docking studies of pyrazole-imidazole-triazole hybrids

Punia, Suman; Verma, Vikas; Kumar, Devinder; Kumar, Ashwani; Deswal, Laxmi

doi:10.1016/j.molstruc.2020.129216

Cited by 19 publications

(8 citation statements)

References 21 publications

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“…The observed difference in inhibitory activity between the various 6a – m hybrid compounds investigated may be related to the effect and nature of the substituents of the phenyl rings (Ar and Ar 1 ) of the pyrazole and isoxazoline cores. This is consistent with reported works in the literature that demonstrate how electron-donating and electron-withdrawing substituents like nitro, chlorine, bromine, methyl, and methoxy groups affect biological activity. − As the obtained results indicate, some compounds with specific substituents turned out to be more active. Among the examined hybrids, compound 6d (Ar = p -Cl(C 6 H 4 ), Ar 1 = p -Cl(C 6 H 4 ) displays the best antibacterial activity against S.…”

Section: Resultssupporting

confidence: 91%

“…This is consistent with reported works in the literature that demonstrate how electron-donating and electron-withdrawing substituents like nitro, chlorine, bromine, methyl, and methoxy groups affect biological activity. 56 − 58 As the obtained results indicate, some compounds with specific substituents turned out to be more active. Among the examined hybrids, compound 6d (Ar = p -Cl(C 6 H 4 ), Ar 1 = p -Cl(C 6 H 4 ) displays the best antibacterial activity against S. aureus with an inhibition zone of (18 ± 03) mm and a percentage of inhibition of 78.6%, as compared to the reference antibiotic, ampicillin (23 ± 0.5) mm.…”

Section: Resultsmentioning

confidence: 66%

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Synthesis, Characterization, DFT Mechanistic Study, Antimicrobial Activity, Molecular Modeling, and ADMET Properties of Novel Pyrazole-isoxazoline Hybrids

et al. 2022

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A series of new heterocycle hybrids incorporating pyrazole and isoxazoline rings was successfully synthesized, characterized, and evaluated for their antimicrobial responses. The synthesized compounds were obtained utilizing N-alkylation and 1,3-dipolar cycloaddition reactions, as well as their structures were established through spectroscopic methods and confirmed by mass spectrometry. To get more light on the regioselective synthesis of new hybrid compounds, mechanistic studies were performed using DFT calculations with B3LYP/6-31G(d,p) basis set. Additionally, the results of the preliminary screening indicate that some of the examined hybrids showed potent antimicrobial activity, compared to standard drugs. The results confirm that the antimicrobial activity is strongly dependent on the nature of the substituents linked pyrazole and isoxazoline rings. Furthermore, molecular docking studies were conducted to highlight the interaction modes between the investigated hybrid compounds and the Escherichia coli and Candida albicans receptors. Notably, the results demonstrate that the investigated compounds have strong protein binding affinities. The stability of the formed complexes by the binding between the hybrid compound 6c, and the target proteins was also confirmed using a 100 ns molecular dynamics simulation. Finally, the prediction of ADMET properties suggests that almost all hybrid compounds possess good pharmacokinetic profiles and no signs of observed toxicity, except for compounds 6e, 6f, and 6g.

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Section: Resultssupporting

confidence: 91%

Section: Resultsmentioning

confidence: 66%

Synthesis, Characterization, DFT Mechanistic Study, Antimicrobial Activity, Molecular Modeling, and ADMET Properties of Novel Pyrazole-isoxazoline Hybrids

et al. 2022

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“…Among the synthesized compounds, most of the methyl derivatives in the pyrazole ring had higher activity than the H analogs. In general, these compounds have been shown to be more effective against A. niger than against Candida albicans [100].…”

Section: 23-triazoles-pyrazole Imidazole and Benzimidazolementioning

confidence: 99%

A Recent Overview of 1,2,3-Triazole-Containing Hybrids as Novel Antifungal Agents: Focusing on Synthesis, Mechanism of Action, and Structure-Activity Relationship (SAR)

Marzi

Farjam

Kazeminejad

et al. 2022

Journal of Chemistry

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A pharmacophore system has been found as 1,2,3-triazole, a five-membered heterocycle ring with nitrogen heteroatoms. These heterocyclic compounds can be produced using azide-alkyne cycloaddition processes catalyzed by ruthenium or copper. The bioactive compounds demonstrated antitubercular, antibacterial, anti-inflammatory, anticancer, antioxidant, antiviral, and antidiabetic properties. This heterocycle molecule, in particular, with one or more 1,2,3-triazole cores has been found to have the most powerful antifungal effects. The goal of this review is to highlight recent developments in the synthesis and structure-activity relationship (SAR) investigation of this prospective fungicidal chemical. Also there have been explained drugs and mechanism of action of a triazole compound with antifungal activity. This review will be useful in a variety of fields, including medicinal chemistry, organic chemistry, mycology, and pharmacology.

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“…Pyrazole scaffolds are well authenticated to have powerful innumerable chemical and pharmacological properties. [2] Besides, this class of compounds is one of the most potent bioactive heterocyclic scaffolds revealing various notable biological activities such as antimicrobial, [3,4] antitubercular, [5] anticonvulsant, [6] antipyretic [7,8] and anti-angiogenic. [9] Also, a wide range of antagonistic activities of the metal complexes of pyrazole derivatives including antifungal activity, [7] potent antioxidant enzyme mimics, [10] anti-inflammatory and anticancer have been reported.…”

Section: Introductionmentioning

confidence: 99%

“…Among these compounds are pyrazoles and their derivatives, as they represent a multifaceted platform in pharmaceutical chemistry. Pyrazole scaffolds are well authenticated to have powerful innumerable chemical and pharmacological properties [2] . Besides, this class of compounds is one of the most potent bioactive heterocyclic scaffolds revealing various notable biological activities such as antimicrobial, [3,4] antitubercular, [5] anticonvulsant, [6] antipyretic [7,8] and anti‐angiogenic [9] .…”

Section: Introductionmentioning

confidence: 99%

Convenient Synthesis of Binary and Fused Pyrazole Ring Systems: Accredited by Molecular Modeling and Biological Evaluation

et al. 2020

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Binary and fused pyrazole ring systems have been synthesized through treatment of dehydroacetic acid (DHA) with different hydrazines. The geometrical studies were performed based on the density functional theory (DFT). This study assured the selectivity of chemical behavior of dehydroacetic acid towards binucleophilic reagent. Furthermore, the new synthesized compounds were evaluated antioxidant and anticancer agents.

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Facile synthesis, antimicrobial evaluation and molecular docking studies of pyrazole-imidazole-triazole hybrids

Cited by 19 publications

References 21 publications

Synthesis, Characterization, DFT Mechanistic Study, Antimicrobial Activity, Molecular Modeling, and ADMET Properties of Novel Pyrazole-isoxazoline Hybrids

Synthesis, Characterization, DFT Mechanistic Study, Antimicrobial Activity, Molecular Modeling, and ADMET Properties of Novel Pyrazole-isoxazoline Hybrids

A Recent Overview of 1,2,3-Triazole-Containing Hybrids as Novel Antifungal Agents: Focusing on Synthesis, Mechanism of Action, and Structure-Activity Relationship (SAR)

Convenient Synthesis of Binary and Fused Pyrazole Ring Systems: Accredited by Molecular Modeling and Biological Evaluation

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