Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners
Mohamed Ramadan El Sayed Aly1, Hosam Ali Saad2, Shams Hashim Abdel-Hafez3
1Chemistry Department, Faculty of Science, Taif University, 21974-Hawyah-Taif, Kingdom of Saudi Arabia ; Chemistry Department, Faculty of Applied Science, Port Said University, 42522-Port Said, Egypt.
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.
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