Synthesis, spectroscopic (IR and NMR), HOMO-LUMO, NLO, molecular docking and ADME study of (E)-2-(2-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene) hydrazineyl)-4-(4-nitrophenyl)thiazole

The three component reaction between 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4- carbaldehyde, thio-semicarbazide and 4-nitrophenacyl bromide furnished (E)-2-(2-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl) methylene)hydrazineyl)-4-(4 nitrophenyl)thiazole which was characterized by FT-IR and NMR spectral methods. These spectroscopic methods confirmed the structural framework of the titled compound. The density functional theory (DFT) approach with a 6-311++G(d,p) method was used and electronic and spectroscopic parameters were analyzed. Frontier molecular orbital analysis of the titled compound found a 3.13 eV energy gap with HOMO primarily populated on pyrazole and thiazole rings whereas LUMO populated on benzene carrying nitro group. According to the Non-Linear Optical (NLO) study, the titled compound might be significant in the fabrication of nonlinear optical materials. The results of the in-silico molecular docking study against cytochrome P450 14-sterol demethylase (CYP51) showed that hydrogen bonds, aromatic and hydrophobic interactions, and van Der Waals forces all contributed to strong binding affinity with the ligand. The experimental and compu-tational spectral comparison led assignments of IR and NMR signals. The ADME predictions suggested a good pharmacological profile of the titled compound.