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Article

New Quinazolin-4(3H)-one Derivatives Incorporating Hydrazone and Pyrazole Scaffolds as Antimicrobial Agents Targeting DNA Gyraze Enzyme

1
Department of Therapeutic Chemistry, National Research Centre, Dokki, Cairo 12622, Egypt
2
Department of Pharmaceutical Medicinal Chemistry, Faculty of Pharmacy (Girls), Al-Azhar University, Cairo 11754, Egypt
3
Department of Microbial Chemistry, National Research Centre, Dokki, Cairo 12622, Egypt
*
Author to whom correspondence should be addressed.
Academic Editor: William A. Donaldson
Sci. Pharm. 2022, 90(3), 52; https://doi.org/10.3390/scipharm90030052
Received: 2 August 2022 / Revised: 14 August 2022 / Accepted: 17 August 2022 / Published: 26 August 2022
(This article belongs to the Special Issue Feature Papers in Scientia Pharmaceutica)
The present work includes the synthesis of a new series of quinazolin-4(3H)-one compounds (4af, 5ad) as antimicrobial agents. The starting compound, 2-hydrazinylquinazolin-4(3H)-one (2), was synthesized and treated with different carbonyl compounds to afford the hydrazone derivatives 4af. In addition, the hydrazone derivatives 4ad were treated with a DMF/POCl3 mixture to give the formyl-pyrazole derivatives 5ad. All the target compounds were evaluated as antimicrobial agents against four bacterial and four fungal strains. The majority of the tested compounds showed potent antimicrobial activity compared with the reference antibiotics. The most potent antimicrobial activity was shown by 5a with MIC values in the range (1–16) μg/mL. In addition, the most potent compounds against E. coli were evaluated for their inhibitory activity against E. coli DNA gyrase, whereas the target compounds 4a, 5a, 5c, and 5d showed the most potent inhibition to the target enzyme with IC50 values ranging from 3.19 to 4.17 µM. Furthermore, molecular docking studies were performed for the most active compounds against the target E. coli DNA gyrase to determine their binding affinity within the enzyme’s active site. Moreover, ADME evaluations of these compounds predicted their high oral bioavailability and good GI absorption. View Full-Text
Keywords: quinazolin-4(3H)-ones; hydrazones; 4-formylpyrazoles; antimicrobial evaluation; DNA gyrase inhibitors; molecular docking; ADME studies quinazolin-4(3H)-ones; hydrazones; 4-formylpyrazoles; antimicrobial evaluation; DNA gyrase inhibitors; molecular docking; ADME studies
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MDPI and ACS Style

Mohi El-Deen, E.M.; Nossier, E.S.; Karam, E.A. New Quinazolin-4(3H)-one Derivatives Incorporating Hydrazone and Pyrazole Scaffolds as Antimicrobial Agents Targeting DNA Gyraze Enzyme. Sci. Pharm. 2022, 90, 52. https://doi.org/10.3390/scipharm90030052

AMA Style

Mohi El-Deen EM, Nossier ES, Karam EA. New Quinazolin-4(3H)-one Derivatives Incorporating Hydrazone and Pyrazole Scaffolds as Antimicrobial Agents Targeting DNA Gyraze Enzyme. Scientia Pharmaceutica. 2022; 90(3):52. https://doi.org/10.3390/scipharm90030052

Chicago/Turabian Style

Mohi El-Deen, Eman M., Eman S. Nossier, and Eman A. Karam. 2022. "New Quinazolin-4(3H)-one Derivatives Incorporating Hydrazone and Pyrazole Scaffolds as Antimicrobial Agents Targeting DNA Gyraze Enzyme" Scientia Pharmaceutica 90, no. 3: 52. https://doi.org/10.3390/scipharm90030052

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