Synthesis, characterization, molecular docking and exploration of biological activities of 3,5-diaryl, diimino, 4-(aryl amino)-1,2,4 dithiazolidine

Abstract

Dithiazolidines are a type of organic compound with a dithiazolidine ring that contains two nitrogen atoms and two sulfur atoms arranged in a specific way. These compounds can have various functional groups and substituents attached to the ring, which changes their reactivity and chemical properties. Dithiazolidines may play an important role in several areas, such as coordination chemistry, material science for creating new materials or modifying existing ones, medicinal chemistry, and organic synthesis as building blocks for more complex molecules. Due to their unique structures and ways of functioning, researchers have looked into dithiazolidine derivatives for their possible use as antimicrobial agents. In this study, N-aryl-S-chloro isothiocarbamoyl chloride was formed by refluxing p-phenylene diamine and aryl isothiocyanate with chloroform.

Dithiazolidines are a class of organic compounds with a dithiazolidine ring, consisting of two sulfur atoms and two nitrogen atoms arranged with specific linkage. These compounds can have various substituents and functional groups attached to the ring, which changes their chemical properties and reactivity. Dithiazolidines plays an important role several fields, like organic synthesis, as intermediates to construct more complex molecules; medicinal chemistry; material science for creating new materials or modifying existing ones; and coordination chemistry. Due to  unique structures and mechanisms of action, Dithiazolidine derivatives have been explored for their potential as antimicrobial agents. In this research, Aryl isothiocyanate and p-phenylene diamine were refluxed with chloroform to produce N-aryl-S-chloro isothiocarbamoyl chloride. This compound, along with aryl isothiocyanate, underwent chlorination and subsequent cyclization to produce 3,5-diaryl, diimino, 4-(aryl amino) 1,2.4 dithiazolidine. The synthesized products were characterized by spectral and analytical studies like IR, NMR, and mass spectral studies. Their antimicrobial activities was also checked and they showed moderate to good antibacterial as well as antifungal activities. The study highlights the potential of dithiazolidine derivatives as antimicrobial agents, demonstrating their moderate to good activity against selected bacterial and fungal strains. These findings suggest further exploration of dithiazolidines in medicinal chemistry and other applications. Furthermore, the exact binding mode to the selected target proteins for newly synthesized dithiazolidines is determined by performing docking analysis which confirmed well correlation with the experimental observations as per docking results.