Antimicrobial Activities of Some Pyrazoline and Hydrazone Derivatives

Aksöz, Begüm Evranos; Gürpınar, Suna Sibel; Eryılmaz, Müjde

doi:10.4274/tjps.galenos.2019.42650

Cited by 6 publications

(4 citation statements)

References 18 publications

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“…Pyrazolines are noted for the stability of their ring system and the reactivity of several sites that permit a series of substitution reactions to take place. Pyrazoline derivatives are electron-rich compounds displaying a wide variety of biological activities, as reported recently [ 18 , 19 ]. The fusion of the pyrazole ring with a benzene ring produces the indazole system, a 10 π-electron heteroaromatic system characterized by three tautomeric forms generated through prototropic annular tautomerism.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Evaluation of New Pyrazoles, Indazoles and Pyrazolines Prepared in Continuous Flow Mode

Burke

Filippo

Spiccio

et al. 2023

IJMS

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Multi-drug resistant bacterial strains (MDR) have become an increasing challenge to our health system, resulting in multiple classical antibiotics being clinically inactive today. As the de-novo development of effective antibiotics is a very costly and time-consuming process, alternative strategies such as the screening of natural and synthetic compound libraries is a simple approach towards finding new lead compounds. We thus report on the antimicrobial evaluation of a small collection of fourteen drug-like compounds featuring indazoles, pyrazoles and pyrazolines as key heterocyclic moieties whose synthesis was achieved in continuous flow mode. It was found that several compounds possessed significant antibacterial potency against clinical and MDR strains of the Staphylococcus and Enterococcus genera, with the lead compound (9) reaching MIC values of 4 µg/mL on those species. In addition, time killing experiments performed on compound 9 on Staphylococcus aureus MDR strains highlight its activity as bacteriostatic. Additional evaluations regarding the physiochemical and pharmacokinetic properties of the most active compounds are reported and showcased, promising drug-likeness, which warrants further explorations of the newly identified antimicrobial lead compound.

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Section: Introductionmentioning

confidence: 99%

Antimicrobial Evaluation of New Pyrazoles, Indazoles and Pyrazolines Prepared in Continuous Flow Mode

Burke

Filippo

Spiccio

et al. 2023

IJMS

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“…Chalcones have been reported to exhibit a wide range of pharmacological activities such as antimicrobial [10][11][12][13], anticancer [14][15][16], anti-inflammatory [17][18][19], antiviral [20], and antioxidant [21,22]. Furthermore, heterocyclic compounds each bearing a pyrazoline scaffold have been reported as antimicrobial [23][24][25], anticancer [26][27][28], anti-inflammatory [29][30][31], antiviral [32], and antioxidant [33].…”

Section: Introductionmentioning

confidence: 99%

“…matory [17][18][19], antiviral [20], and antioxidant [21,22]. Furthermore, heterocyclic compounds bearing pyrazoline scaffolds have been reported as antimicrobial [23][24][25], anticancer [26][27][28], anti-inflammatory [29][30][31], antiviral [32], and antioxidant [33].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antimicrobial Properties, and Molecular Docking of Novel Furan-Derived Chalcones and Their 3,5-Diaryl-∆2-pyrazoline Derivatives

Mahdi,

Abdula,

Jassim

et al. 2023

Antibiotics

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The present work focuses on the synthesis and preliminary structure activity relationships (SARs) of furan-derived chalcones and their corresponding ∆2-pyrazoline derivatives as antimicrobial agents. Eight novel chalcone derivatives and eight ∆2-pyrazoline compounds were synthesized in moderate to good isolated yields. The target compounds were evaluated as antimicrobial agents against two Gram-positive (Staphylococcus aureus and Staphylococcus epidermidis), two Gram-negative (Escherichia coli and Klebsiella pneumoniae), and fungi (Candida albicans) species. Based on the SARs, chalcones 2a and 2h showed inhibition activity on all tested microbial species, while ∆2-pyrazoline 3d was found to be selective for some microbial species. The most potent compounds (2a, 2h, and 3d) were docked into glucosamine-6-phosphate synthase (GlcN-6-P), the molecular target enzyme for antimicrobial agents, utilizing the Autodock 4.2 program, in order to study their virtual affinity and binding mode with the target enzyme. The selected potent compounds were found to bind to the active site of the enzyme probably in a similar way to that of the substrate as suggested by the docking study. In summary, the newly developed furan-derived chalcones and their ∆2-pyrazoline derivatives could serve as potent leads toward the development of novel antimicrobial agents.

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“…These ring systems inhibit cyclooxygenase enzymes, particularly the COX-2 enzyme [10][11][12][13][14][15][16]. It is thought that these compounds, whose antidepressant and antimicrobial activities we have previously published [17][18][19], may inhibit the COX enzymes because of their similarity to celecoxib (Figure 1), which is a selective COX-2 inhibitor in terms of chemical structure and also carrying a 4,5-dihydro-1Hpyrazole ring in their structure. In this study, molecular docking interactions of some 4,5-dihydro-1Hpyrazole derivatives with COX-1 and COX-2 enzymes were investigated.…”

Section: Introductionmentioning

confidence: 99%

Molecular Docking Studies on Some 4,5-Dihydro-1h-Pyrazole Derivatives as Cyclooxygenase Inhibitors

Aksöz¹

2021

Ankara Universitesi Eczacilik Fakultesi Dergisi

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Objective: To examine the interactions of some 4,5-dihydro-1H-pyrazole derivatives, which are thought to have antiinflammatory effects, with cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) enzymes, docking studies were carried out on these enzymes.Material and Method: COX-1 enzyme (3KK6) and COX-2 enzyme (3LN1) were selected from the protein data bank for docking studies. The ligand and protein constructs were prepared using Autodock 1.5.6. AutoDock Vina was used to determining the binding affinity, and Discovery Studio 3.5 was utilised to analyse and display the docking results.Result and Discussion: As a result of the docking process on COX-1 and COX-2 enzymes, 4,5-Dihydro-1H-pyrazole derivatives were observed to interact with both enzymes. The 4,5-dihydro-1H-pyrazole ring was found to be important in its interactions with the COX-2 enzyme. The inclusion of a bulky group in the construct did not cause any problems in interaction with the COX-1 enzyme but eliminated some interactions with the COX-2 enzyme. To better elucidate the inhibition properties of enzymes, this study should be supported by in vitro and in vivo COX inhibition tests.

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Antimicrobial Activities of Some Pyrazoline and Hydrazone Derivatives

Cited by 6 publications

References 18 publications

Antimicrobial Evaluation of New Pyrazoles, Indazoles and Pyrazolines Prepared in Continuous Flow Mode

Antimicrobial Evaluation of New Pyrazoles, Indazoles and Pyrazolines Prepared in Continuous Flow Mode

Design, Synthesis, Antimicrobial Properties, and Molecular Docking of Novel Furan-Derived Chalcones and Their 3,5-Diaryl-∆2-pyrazoline Derivatives

Molecular Docking Studies on Some 4,5-Dihydro-1h-Pyrazole Derivatives as Cyclooxygenase Inhibitors

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