Synthesis, Characterization, Molecular Docking Studies and Exploration of Antimicrobial Activities of 3,5 Diaryl, Diimino, 4(Aryl Amino) 1,2,4 Dithiazolidine

Abstract

Dithiazolidines represent a special unique class of organic compounds characterized by a distinct heterocyclic ring containing two sulfur and two nitrogen atoms with a specific arrangement. Introduction of various substituents or functional groups changes their chemical behavior and reactivity and makes them valuable in diverse applications in fields such as organic synthesis, medicinal chemistry, materials science, and coordination chemistry. Due to to their unique structural features as well as mechanism of action, various derivatives of dithiazolidines have attracted attention for their potential antimicrobial activities. In this study, N‑aryl‑S‑chloro isothiocarbamoyl chloride is synthesized by reacting aryl isothiocyanates with p-phenylenediamine by reflux in chloroform. This intermediate compound on chlorination which subsequently followed by cyclization, forms 3,5‑diaryl, diimino, 4‑(aryl amino)‑1,2,4‑dithiazolidines. The synthesized compounds containing different aryl substituents were characterized using Infrared (IR), Nuclear Magnetic Resonance (NMR), and Mass Spectroscopic techniques. Biological screening for antibacterial and antifungal activity against selected microbial strains was done which revealed that these newly synthesized derivatives exhibited moderate to significant activity. Furthermore, molecular docking studies were also performed to investigate the binding interactions of these newly synthesized dithiazolidines derivatives with target proteins. The molecular docking results showed good agreement with the experimental findings. This reinforces the potential of these compounds as a promising scaffold for antimicrobial drug development. Overall, this work highlights the promising use of dithiazolidine derivatives in medicinal chemistry and encourages further exploration of their applications.