Synthesis, characterization, molecular docking, ADME and biological evaluation of 3-(4-(tetrazol-1-yl)phenyl)-5-phenyl-1H-pyrazoles

Abstract

A series of multi-heterocyclic anti-bacterial drugs 3-(4-(tetrazol-1-yl)phenyl)-5-phenyl-1H-pyrazoles are synthesized using the reaction with (E)-1-(4-(1H-tetrazol-1-yl)phenyl)-3-arylprop-2-en-1-one and hydrazine hydrate in the presence of weak acidic catalyst like acetic acid. The structures of synthesized compounds were confirmed by various spectral studies. Biological activity was measured antibacterial studies with MTT assay methods. The parameters such as optimized geometry, electronic properties and hyperpolarizability of the tetrazole containing pyrazoles have been calculated using density functional theory (DFT) with the application of hybrid functional “B3LYP”. In fact, a good agreement between the calculating mode with the experimental one was attained using at the B3LYP/6-311G theoretical level. The molecular electrostatic potential (MEP), thermodynamic properties, electrical dipole moment and the static first hyperpolarizability values were computed for the new molecules. The molecular orbitals HOMO and LUMO, ionization potentials (IPs) and the electron affinities (EAs) of the pyrazole derivatives under study were also investigated. The electron donor and acceptor properties were determined using the natural bond orbital analysis. The molecular docking studies were performed by Discovery studio. Additionally, the pharmacokinetic properties were also predicted. The nature of transitions observed in the ultraviolet–visible spectrum of the title molecule was evaluated using TD-DFT method. The calculated energy and the oscillator strength were almost relatively reproduces the experimental data.