Synthesis and Characterization Of (E)-4-Chloro-2-((4-(Dimethylamino)-2-Hydroxybenzylidene) Amino) Phenol and (E)-4-Bromo-N-(Pyridin-2-Ylmethylene) Aniline Towards Biological Evaluation of Antimicrobial, Antioxidant, Molecular Docking, and ADMET Studies

Abstract

Halogenated Schiff a versatile class of biologically active compounds with potential antimicrobial and antioxidant properties. In this present study, two novel derivatives, (E)-4-chloro-2-((4-(dimethylamino)-2-hydroxybenzylidene)amino)phenol (CDHBP) and (E)-4-bromo-N-(pyridin-2-ylmethylene)aniline (BPMA), were synthesized via condensation reactions and it’s physico-chemical characterization was done by ¹H NMR, and ¹³C NMR spectroscopy. Their biological activities, such as antimicrobial, Minimum Inhibitory Concentration (MIC), antioxidant, and hemolytic compatibility was done. CDHBP showed antifungal activity against Candida albicans (MIC = 32 µg/mL) but showed moderate antibacterial effect, while BPMA shows moderate antibacterial activity for Staphylococcus aureus and Enterococcus faecalis. Hemolytic studies confirmed the biocompatibility of CDHBP at 500 ug/mL as 6% of lytic properties. Molecular docking analysis showed excellent interactions (binding energy -7.60 and strong hydrogen bond interaction) of CDHBP with lanosterol 14-demethylase and in silico ADMET analysis shows high intestinal absorption with low cardiotoxic and hepatotoxic risks, however it’s low solubility and potential genotoxicity requires further investigation. Overall, the study focus on importance of structural relevance on the biological and pharmacokinetic profiles of halogenated Schiff bases and provides a understating of its therapeutic potential for future optimization toward drug development.