Green synthesis of hydrazono-thiazolones using vitamin B1 and their antibacterial implications

Abstract

The study focuses on green methodologies in synthetic organic chemistry, emphasizing the use of thiamine hydrochloride (Vitamin B1) as an eco-friendly catalyst for synthesizing hydrazono-thiazolones. These compounds serve as versatile core units with various therapeutic activities, including anti-HIV, anti-tubercular, antifungal, antiviral, and anticancer properties. Building on prior research involving sustainable barium oxide-chitosan nanocomposite catalysts, this novel green synthetic approach contributes to the sustainable synthesis of bioactive heterocycles. The synthesized compounds 6a-l were tested in vitro against different bacterial species, revealing notable activity against Gram-positive and Gram-negative bacteria. The MIC investigation showed that compounds 6d, 6e, 6j, and 6k have broad-spectrum antibacterial potential, with 6j and 6k being especially effective, their MICs near those of ciprofloxacin, highlighting their strong antibacterial capabilities. Molecular docking studies predicting the binding mode of the most potent substances to Escherichia coli DNA gyrase (PDB ID 4DUH) aligned well with in vitro studies, confirming the new ligands’ potency as potential antimicrobial agents. In silico investigations for the most potent substances revealed a favorable ADME profile, suggesting promising pharmacological properties. This research contributes to both sustainable synthesis and potential therapeutic applications of hydrazono- thiazolone derivatives.