Synthesis, molecular structure, spectral characterization, and biological activities of ethyl 2-(4-(4-chlorobenzyl)-3-methyl-6-oxopyridazin-1(6H)-yl)acetate

Abstract

The structure of the ethyl 2-(4-(4-chlorobenzyl)-3-methyl-6-oxopyridazin-1(6H)-yl)acetate (COAP) was revealed using single crystal X-ray diffraction method, was solved and refined using the Bruker SHELXTL Software Package, using the space group P 1 21/n 1, with Z = 4 for the formula unit, C16H17ClN2O3. Its spectroscopic and electronic properties were investigated by spectroscopic methods such as 1H and 13C NMR, FT-IR and UV–vis. The electronic structure properties of the compound were investigated with quantum mechanical calculations. It was observed that crystal packaging is provided by CH…O type hydrogen bonds. Also, spectroscopic properties such as FT-IR vibrational wave numbers, proton and carbon NMR chemical shifts and UV–vis. absorption parameters were calculated. In addition, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) analyses and Molecular Electrostatic Potential (MEP) surface, NBO analysis were computed to understand the reactive regions of the title compound. All computations were performed by using DFT/B3LYP quantum chemical method with 6–311++G(d,p) basis set to compare with the experimental results. The calculations showed that HOMO orbitals localized on π and n orbitals of pyridazine while LUMO orbitals localized on π* orbitals of pyridazine. The major contribution to electronic transitions originated from HOMO LUMO transition calculated at 292.16 nm. Hirshfeld surface analysis was investigated to visualization van der Waals distances, and the space occupied by molecules and to determine the contact regions. The computed geometry parameters and vibrational wavenumbers were in good agreement with the experimental results. Moreover, the potential inhibitory activities of the compound were evaluated on enzymes α-glucosidase. Besides, the compound was tested for it potential in vitro anti-inflammatory activities by Heat induced hemolysis. The results showed that the product had a good percentage of heat induced Hemolysis inhibition.