Novel organophosphonates based on the pyrazole moiety as potent antimicrobial agents: synthesis, characterization, molecular docking studies, and DFT calculations | ||||
| Egyptian Journal of Chemistry | ||||
| Articles in Press, Accepted Manuscript, Available Online from 01 September 2025 | ||||
| Document Type: Original Article | ||||
| DOI: 10.21608/ejchem.2025.405317.12064 | ||||
 View on SCiNiTO | ||||
| Authors | ||||
Mansoura Ali 1; Basma Ghazal2; Mohamed Abdelaziz 3; Marwa El-Hussieny  4
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| 1National Research Centre,Dept. of Organometallic and Organometalloid Chemisry | ||||
| 2National Research Center | ||||
| 3National research Center | ||||
| 4Organometallic and Organometalloid Chemistry Department, Chemical Industries Division, NRC, Egypt. | ||||
| Abstract | ||||
| In the present study, trimethoxy-oxaphosphol-pyrazol-3-one and dimethyl-pyrazoloxobutylphosphonate derivatives were produced when chalcones incorporated pyrazolone ring 1a,b interacted with trimethyl phosphite in a free solvent setting with palladium acetate acting as a catalyst. However using dialkyl phosphites resulted in a phosphonate derivative. Moreover, organophosphonte derivatives have been prepared via the reaction of pyrazole substrates and dialkyl phosphites. On the other hand, bis(dimethylamino) phosphorylpropanoyl methane and bis(dimethylamino) phosphorylpropanoyl benzene were prepared through the reaction of 5-pyrazolones with hexamethylphosphinetriamine. Spectroscopic analysis was performed to confirm the structure of all new compounds. The in-vitro antibacterial and antifungal activities for all new synthesized compounds were carried out. The obtained results are compared with the reference antibiotics namely, Neomycin (bactericide) and Cyclohexamide (fungicide). Additionally, all of the substances under study showed good to moderate activity compared to the standards, according to the Minimum Inhibitory Concentration (MIC) measurements. The geometry of the compounds was adjusted using density function theory (DFT) at B3LYP using 6-311 G (d,p) basis in order to investigate the electronic characteristics and reactivity of all the compounds under study. Additionally, by inhibiting Dihydropteroate synthase, the molecular docking methodology shows the antibacterial activity of the created compounds, and all of the designed compounds have demonstrated notable drug-like properties. | ||||
| Keywords | ||||
| Chalcones; oxaphosphole; molecular docking; DFT; antimicrobial agents; MIC | ||||
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