Molecular properties and In silico bioactivity evaluation of (4-fluorophenyl)[5)-3-phen-(4-nitrophenyl yl-4,5-dihydro-1 H -pyrazol-1-yl]methanone derivatives: DFT and molecular docking approaches.

Autor: Omotayo IA; Computational Chemistry Laboratory, Department of Pure and Applied Chemistry, Ladoke Akintola University of Technology, Ogbomoso, Nigeria., Banjo S; Computational Chemistry Laboratory, Department of Pure and Applied Chemistry, Ladoke Akintola University of Technology, Ogbomoso, Nigeria., Emmanuel OT; Computational Chemistry Laboratory, Department of Pure and Applied Chemistry, Ladoke Akintola University of Technology, Ogbomoso, Nigeria., Felix LD; Department of Pure and Applied Chemistry, Osun State University, Osogbo, Nigeria., Kolawole OA; Department of Chemistry and Industrial Chemistry, Bowen University, Iwo, Nigeria., Dele OA; Department of Chemistry, Emmanuel Alayande College of Education, Nigeria., Olasegun AI; Department of Chemistry, Nigerian Army University, Biu, Nigeria., Dasola AM; Department of Chemical Sciences, Fountain University, Osogbo, Nigeria., Ayobami OO; Computational Chemistry Laboratory, Department of Pure and Applied Chemistry, Ladoke Akintola University of Technology, Ogbomoso, Nigeria.; Department of Chemistry, Faculty of Natural and Applied Sciences, Hallmark University, Ijebu-Itele, Nigeria.
Jazyk: angličtina
Zdroj: Journal of Taibah University Medical Sciences [J Taibah Univ Med Sci] 2023 May 23; Vol. 18 (6), pp. 1386-1405. Date of Electronic Publication: 2023 May 23 (Print Publication: 2023).
DOI: 10.1016/j.jtumed.2023.05.011
Abstrakt: Objectives: Molecular structures, spectroscopic properties, charge distributions, frontier orbital energies, nonlinear optical (NLO) properties and molecular docking simulations were analyzed to examine the bio-usefulness of a series of (4-fluorophenyl)[5-(4-nitrophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]methanone derivatives.
Methods: The compounds were studied through computational methods. Equilibrium optimization of the compounds was performed at the B3LYP/6-31G(d,p) level of theory, and geometric parameters, frequency vibration, UV-vis spectroscopy and reactivity properties were predicted on the basis of density functional theory (DFT) calculations.
Results: The energy gap (ΔEg), electron donating/accepting power ( ω -/ ω +) and electron density response toward electrophiles/nucleophiles calculated for M1 and M2 revealed the importance of substituent positioning on compound chemical behavior. In addition, ω -/ ω + and ΔEn/ΔEe indicated that M6 is more electrophilic because of the presence of two NO 2 groups, which enhanced its NLO properties. The hyperpolarizability (β 0 ) of the compounds ranged from 5.21 × 10 -30 to 7.26 × 10 -30  esu and was greater than that of urea; thus, M1-M6 were considered possible candidates for NLO applications. Docking simulation was also performed on the studied compounds and targets (PDB ID: 5ADH and 1RO6 ), and the calculated binding affinity and non-bonding interactions are reported.
Conclusion: The calculated ω - and ω + indicated the electrophilic nature of the compounds; M6 , a compound with two NO 2 groups, showed enhanced effects. Molecular electrostatic potential (MEP) analysis indicated that amide and nitro groups on the compounds were centers of electrophilic attacks. The magnitude of the molecular hyperpolarizability suggested that the entire compound had good NLO properties and therefore could be explored as a candidate NLO material. The docking results indicated that these compounds have excellent antioxidant and anti-inflammatory properties.
(© 2023 The Authors.)
Databáze: MEDLINE
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