Synthesis of Novel Cholesteryl Carbamate Derivatives

Nine novel cholesterol-derived carbamate derivatives, were synthesised by reacting cholesteryl chloroformate with various amines, including urea, acetamide, acrylamide, thiocarbazide, 4-methylthiosemicarbazide, aniline, p-methoxy benzylamine, 4-aminoquinaldine and piperidine. The derivatives contain diverse functional groups, such as carbamate linkages, sulphur-containing moieties, aromatic rings and aliphatic amines. The use of 4-dimethyl amino pyridine (DMAP) as a catalyst reduced the reaction time from 24 h to 12 h. The reactions proceeded under mild conditions, with yields varying based on the nature of the amine. Secondary aliphatic amines afforded the highest yields, followed by hydrazine-based carbamates. The synthesised compounds were characterised using NMR spectroscopy, mass spectrometry. These cholesteryl carbamates provide a versatile platform for further modifications and show potential applications in chemical sensing, biomaterials and drug delivery.