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

Abstract

BackgroundNowadays, 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.ResultA 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.ConclusionsDensity 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.Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0492-4) contains supplementary material, which is available to authorized users.

Novel β-keto–enol Pyrazolic Compounds as Potent Antifungal Agents. Design, Synthesis, Crystal Structure, DFT, Homology Modeling, and Docking Studies

“…The inhibitory concentration (IC 50 ) is lower for these active compounds 2 , 8 , 9 and 10 with IC 50 values of 71.00, 48.00, 14.80, and 53.00 μM, respectively, than the other compounds. Compared to our previous works in this era, these findings present the best obtained results for all the already tested analog products of this family against FOA fungus …”

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

“…The selected compounds are all the testes against F.o.a., collected from the references (Waring et al, 2002;Radi et al, 2012Radi et al, , 2015Smaail et al, 2012;Boussalah et al, 2013;Loth et al, 2015;Abrigach et al, 2017Abrigach et al, , 2018Tighadouini et al, 2018Tighadouini et al, , 2019Koudad et al, 2019;Toubi et al, 2019).…”

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

“…[6][7][8] This substance class has been the topic of numerous pharmaceutical studies being used for their medicinal properties such as anti-inammatory, 9 antidiabetic, 10,11 antiviral, 12 analgesic, 13 antitumor, 14 catecholase, 15 and antimicrobial properties. 16 On other hand, nitrogen systems have attracted more attention in recent years because of their interesting properties in coordination chemistry. [17][18][19] However, many reports on transition metal complexes explain their efficient bioactivity against a range of bacterial and fungal species.…”

“… 6–8 This substance class has been the topic of numerous pharmaceutical studies being used for their medicinal properties such as anti-inflammatory, 9 antidiabetic, 10,11 antiviral, 12 analgesic, 13 antitumor, 14 catecholase, 15 and antimicrobial properties. 16 …”