Novel Trifluoromethyl Containing Azo-Imin compounds: Synthesis, Characterization, and Investigation of Antioxidant Properties Using In Vitro and In Silico methods

Abstract: In this study, two new molecules 4-((4-methoxyphenyl)diazenyl)-2-(((4-(trifluoromethyl)phenyl)imino)methyl)phenol (3a) and 2-(((4-methoxyphenyl)imino)methyl)-4-((4-(trifluoromethyl)phenyl)diazenyl)phenol (3b) were synthesized. The 1H-NMR, FTIR, UV-vis, and Mass analysis techniques were used to confirm the structures of the 3a and 3b. CUPRAC in vitro antioxidant activity method was also used to investigate the antioxidant properties of synthesized compounds. The compounds' ADME and toxicity parameters were also computed using SwissADME, Protox-II web servers respectively. In silico Molecular docking studies were conducted utilizing four different antioxidant proteins, such as PDB ID: 1N8Q for Lipoxygenase, 1OG5 for CYP2C9, 2CDU for NADPH oxidase, and 4JK4 for Bovine Serum Albumin, to investigate the potential antioxidant properties of the synthesized compounds 3a and 3b. ADME and toxicity (ADMEt) results showed that pharmacokinetic, physico-chemical, drug-similarity, and toxicity data were all appropriate for a potential bioactive agent. Molecular docking results have shown that all docking results were higher than standard (Trolox). The best docking score (-9.4 kcal/mol) was between 3b ligand and 2CDU protein. TEAC values of compounds were also higher than standard which was in harmony with molecular docking scores. From all obtained data It was concluded that the compound 3b has the potential antioxidant agent.