One-Pot Multicomponent Synthesis of Thiourea Derivatives in Cyclotriphosphazenes Moieties

Abstract EN

In this study, hexasubstituted thiourea was carried out via reaction of isothiocyanato cyclophosphazene intermediates with a series of aromatics amines and amino acids in a one-pot reaction system.

The reaction was not as straightforward as typical thiourea synthesis.

Six unexpected thiourea derivatives 3a–f were formed in the presence of cyclotriphosphazene moieties in good yields (53–82%).

The structures of 3a–f were characterized by elemental analysis and FTIR, 1H, 13C, and 31P NMR spectroscopies.

The occurrence of reverse thioureas formation in a one-pot reaction system is discussed.

The possible binding interaction of the synthesised thiourea 3a-b in comparison to the predicted phenyl thiourea 5a-b and the targeted 4a with enzyme enoyl ACP reductase (FabI) is also discussed.

Molecular docking of the targeted hexasubstituted thiourea 4a is able to give higher binding affinity of −7.5 kcal/mol compared to 5a-b (−5.9 kcal/mol and −6.3 kcal/mol) and thiourea 3a-b (−4.5 kcal/mol and −4.7 Kcal/mol).