Synthesis, Crystal Structure, DFT Studies and Biological Activity of (Z)-3-(3-bromophenyl)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxyprop-2-en-1-one

Overview

Journal Chem Cent J

Publisher Biomed Central

Specialty Chemistry

Date 2018 Nov 27

PMID 30474759

Citations 6

Authors

Said Tighadouini

Redouane Benabbes

Monique Tillard

Driss Eddike

Khadija Haboubi

Khalid Karrouchi

Smaail Radi

Affiliations

Soon will be listed here.

Abstract

Background: Nowadays, is emerging a new generation of highly promising inhibitors bearing the β-ketoenol functionality. The present work relates to the first synthesis, the structure determination, the DFT studies and the use of a new biomolecule designed with a β-ketoenol group bounded to a pyrazolic moiety.

Result: A novel β-ketoenol-pyrazole has been synthesized, well characterized and its structure was confirmed by single crystal X-ray diffraction. The electron densities and the HOMO-LUMO gap have been calculated using the DFT method with BLYP, PW91, PWC functionals and 6-31G* basis set. An evaluation of the molecule stability is provided by a NBO analysis and the calculated Fukui and Parr functions have been used to locate the reactive electrophile and nucleophile centers in the molecule. The synthesized compound, screened for its in vitro antifungal behavior against the Fusarium oxysporum f.sp. albedinis FAO fungal strains, shows a moderate activity with an inhibition percentage of 46%. The product was also tested against three bacterial strains (Escherichia coli, Bacillus subtilis and Micrococcus luteus), but no significant effect was observed against these organisms.

Conclusions: Density functional calculations are used to evaluate the HOMO-LUMO energy gap, the molecular electrostatic potential and to provide a natural bond orbital analysis. The measured antimicrobial activities encourage us to continue searching for other structures, likely to be good antifungal candidates.

Citing Articles

Synthesis, structural characterizations, in vitro biological evaluation and computational investigations of pyrazole derivatives as potential antidiabetic and antioxidant agents.

Mortada S, Karrouchi K, Hamza E, Oulmidi A, Bhat M, Mamad H Sci Rep. 2024; 14(1):1312.

PMID: 38225280 PMC: 10789823. DOI: 10.1038/s41598-024-51290-6.

New N-Alkylated Heterocyclic Compounds as Prospective NDM1 Inhibitors: Investigation of In Vitro and In Silico Properties.

Kaddouri Y, Bouchal B, Abrigach F, El Kodadi M, Bellaoui M, Elkamhawy A Pharmaceuticals (Basel). 2022; 15(7).

PMID: 35890102 PMC: 9322059. DOI: 10.3390/ph15070803.

An Insight into All Tested Small Molecules against Fusarium oxysporum f. sp. Albedinis: A Comparative Review.

Kaddouri Y, Benabbes R, Ouahhoud S, Abdellattif M, Hammouti B, Touzani R Molecules. 2022; 27(9).

PMID: 35566050 PMC: 9099577. DOI: 10.3390/molecules27092698.

Coordination complexes constructed from pyrazole-acetamide and pyrazole-quinoxaline: effect of hydrogen bonding on the self-assembly process and antibacterial activity.

Chkirate K, Karrouchi K, Chakchak H, Mague J, Radi S, Adarsh N RSC Adv. 2022; 12(9):5324-5339.

PMID: 35425576 PMC: 8981392. DOI: 10.1039/d1ra09027e.

Mono-Alkylated Ligands Based on Pyrazole and Triazole Derivatives Tested Against . sp. : Synthesis, Characterization, DFT, and Phytase Binding Site Identification Using Blind Docking/Virtual Screening for Potent Fophy Inhibitors.

Kaddouri Y, Abrigach F, Ouahhoud S, Benabbes R, El Kodadi M, Alsalme A Front Chem. 2020; 8:559262.

PMID: 33363103 PMC: 7759635. DOI: 10.3389/fchem.2020.559262.

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