Synthesis, structural analysis, Hirshfeld surface analysis, DFT calculations, in vitro and docking study on antioxidant activity of 6-chloro-3-[(4-methylphenoxy) methyl] [1,2,4] triazolo[4,3-b]pyridazine

Abstract

Pyridazine nuclei are essential elements of many natural and synthetic compounds with important biological activities. NMR and IR, as well as studies of mass spectrum, were emplyed to synthesize and characterize the title compound 6-chloro-3-[(4-methylphenoxy) methyl] [1,2,4] triazolo[4,3-b] pyridazine (CMTP). The structure of this compound was confirmed by using single crystal X-ray diffraction technique and it got crystallized in the monoclinic crystal system with the space group P2 1/c. The values of unit cell parameters are: a = 12.0965(7) Å, b = 13.6075(7) Å, c = 7.7686(4) Å, β = 93.942(3)° and Z = 4. Intermolecular hydrogen bonds of two types i.e., C-H…O and C-H…N, were noticed. Hirshfeld surface analysis was employed to account for these interaction bonds. Energy frameworks were carried out to know the dominant interaction energy involved in the molecular packing. DFT calculations were constructed to find the agreement between the theoretical and experimental values. HOMO-LUMO energy levels have been determined; global hardness, global softness, and other quantum chemical parameters have been calculated to reveal the chemical reactivity of the compound. In order to investigate the antioxidant activity of the compound, molecular docking studies were performed.