Abstract
3β-Azidocholest-5-ene (
3
) and (3β)-3-(prop-2-yn-1-yloxy)cholest-5-ene (
10
) were prepared as substrates to synthesize a variety of three-motif pharmacophoric conjugates through CuAAC. Basically, these conjugates included cholesterol and 1,2,3-triazole moieties, while the third, the pharmacophore, was either a chalcone, a lipophilic residue or a carbohydrate tag. These compounds were successfully prepared in good yields and characterized by NMR, MS and IR spectroscopic techniques. Chalcone conjugate
6c
showed the best antimicrobial activity, while the lactoside conjugate
27
showed the best cytotoxic effect in vitro.