Pyrazole as an Anti-Microbial Scaffold: A Comprehensive Review

Kaur, Parminder; Arora, Vimal

doi:10.2174/1570193x20666221031100542

Cited by 4 publications

(1 citation statement)

References 57 publications

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“…Pyrazole, a five-membered heterocyclic ring, is an important scaffold with diverse pharmacological activities such as anticancer, , antimicrobial, , antimalarial, anti-inflammatory, and other activities. − Particularly, the pyrazole ring also plays a crucial role in the development of chemical fungicides. For example, among the 24 commercial SDHI fungicides, up to 12 commercial SDHI fungicides possess a pyrazole fragment (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Novel Pyrazole-4-Carboxamide Derivatives Containing Oxime Ether Group as Potential SDHIs to Control Rhizoctonia solani

Luo,

Wu,

Ren

et al. 2024

J. Agric. Food Chem.

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In the search for novel succinate dehydrogenase inhibitor (SDHI) fungicides to control Rhizoctonia solani, thirty-five novel pyrazole-4-carboxamides bearing either an oxime ether or an oxime ester group were designed and prepared based on the strategy of molecular hybridization, and their antifungal activities against five plant pathogenic fungi were also investigated. The results indicated that the majority of the compounds containing oxime ether demonstrated outstanding in vitro antifungal activity against R. solani, and some compounds also displayed pronounced antifungal activities against Sclerotinia sclerotiorum and Botrytis cinerea. Particularly, compound 5e exhibited the most promising antifungal activity against R. solani with an EC 50 value of 0.039 μg/ mL, which was about 20-fold better than that of boscalid (EC 50 = 0.799 μg/mL) and 4-fold more potent than fluxapyroxad (EC 50 = 0.131 μg/mL). Moreover, the results of the detached leaf assay showed that compound 5e could suppress the growth of R. solani in rice leaves with significant protective efficacies (86.8%) at 100 μg/mL, superior to boscalid (68.1%) and fluxapyroxad (80.6%), indicating promising application prospects. In addition, the succinate dehydrogenase (SDH) enzymatic inhibition assay revealed that compound 5e generated remarkable SDH inhibition (IC 50 = 2.04 μM), which was obviously more potent than those of boscalid (IC 50 = 7.92 μM) and fluxapyroxad (IC 50 = 6.15 μM). Furthermore, SEM analysis showed that compound 5e caused a remarkable disruption to the characteristic structure and morphology of R. solani hyphae, resulting in significant damage. The molecular docking analysis demonstrated that compound 5e could fit into the identical binding pocket of SDH through hydrogen bond interactions as well as fluxapyroxad, indicating that they had a similar antifungal mechanism. The density functional theory and electrostatic potential calculations provided useful information regarding electron distribution and electron transfer, which contributed to understanding the structural features and antifungal mechanism of the lead compound. These findings suggested that compound 5e could be a promising candidate for SDHI fungicides to control R. solani, warranting further investigation.

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Section: Introductionmentioning

confidence: 99%

Novel Pyrazole-4-Carboxamide Derivatives Containing Oxime Ether Group as Potential SDHIs to Control Rhizoctonia solani

Luo,

Wu,

Ren

et al. 2024

J. Agric. Food Chem.

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Antibacterial and antifungal pyrazoles based on different construction strategies

Rehman,

He,

Shu

et al. 2025

European Journal of Medicinal Chemistry

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Synthesis and Anti-Trypanosoma cruzi Activity of New Pyrazole-Thiadiazole Scaffolds

Souza,

Orlando,

Lara

et al. 2024

Molecules

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Chagas disease, a silent but widespread disease that mainly affects a socioeconomically vulnerable population, lacks innovative safe drug therapy. The available drugs, benznidazole and nifurtimox, are more than fifty years old, have limited efficacy, and carry harmful side effects, highlighting the need for new therapeutics. This study presents two new series of pyrazole-thiadiazole compounds evaluated for trypanocidal activity using cellular models predictive of efficacy. Derivatives 1c (2,4-diCl) and 2k (4-NO2) were the most active against intracellular amastigotes. Derivative 1c also showed activity against trypomastigotes, with the detachment of the flagellum from the parasite body being a predominant effect at the ultrastructural level. Analogs have favorable physicochemical parameters and are predicted to be orally available. Drug efficacy was also evaluated in 3D cardiac microtissue, an important target tissue of Trypanosoma cruzi, with derivative 2k showing potent antiparasitic activity and a significant reduction in parasite load. Although 2k potentially reduced parasite load in the washout assay, it did not prevent parasite recrudescence. Drug combination analysis revealed an additive profile, which may lead to favorable clinical outcomes. Our data demonstrate the antiparasitic activity of pyrazole-thiadiazole derivatives and support the development of these compounds using new optimization strategies.

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Pyrazole as an Anti-Microbial Scaffold: A Comprehensive Review

Cited by 4 publications

References 57 publications

Novel Pyrazole-4-Carboxamide Derivatives Containing Oxime Ether Group as Potential SDHIs to Control Rhizoctonia solani

Novel Pyrazole-4-Carboxamide Derivatives Containing Oxime Ether Group as Potential SDHIs to Control Rhizoctonia solani

Antibacterial and antifungal pyrazoles based on different construction strategies

Synthesis and Anti-Trypanosoma cruzi Activity of New Pyrazole-Thiadiazole Scaffolds

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