Efficient synthesis of imino-1,3-thiazinan-4-one promoted by acetonitrile electrogenerated base and computational studies with CB1 and 11 βHSD1 molecules

Abstract

A novel and convenient strategy is described for the conversion of N, N′-disubstituted thioureas and acryloyl chloride into the highly biologically valuable imino-1,3-thiazinan-4-one derivatives. The synthesis proceeds through a process with good yield promoted by an electrogenerated base obtained with high current efficiency. In addition to this, based on structure–activity relationship studies, we have found suitable targets like G-protein coupled (CB1) cannabinoid receptor and human 11 beta-hydroxysteroid dehydrogenase type 1 (11 βHSD1) for this synthesized molecule. The molecular docking studies were carried for our compound with CB1 and 11 βHSD1 to understand the binding interaction mechanism, and molecular dynamics simulations were performed to understand the stability of small molecule in CB1 and 11 βHSD1 microenvironments. Also, to understand the intermolecular stability density functional theory calculations were carried for free compound and compound in complex with CB1 and 11 βHSD1.