Synthesis and cytotoxic evaluation of cholesteryl 6-<em>O</em>-acyl-β-<img src='http://www.niscair.res.in/jinfo/smaller.gif' border=0>-galactopyranosides

91-97In the present study, cholesteryl 6-O-acyl-β--galactopyranosides have been synthesized using trichloroacetimidate methodology with unusual, short, medium, long and unsaturated fatty acids. Glycosylation of cholesterol has been achieved using trichloroacetimidate as donor and TMSOTf as promoter. The β-configuration is confirmed by 1H NMR analysis as the anomeric proton appears atδ 4.55 (d, J1,2 = 7.93 Hz) as a doublet. Acetate groups have been selectively deprotected with Zemplen deacylation after which cholesteryl β--galactopyranoside has been selectively esterified at C-6ʹ position with EDC.HCl. All the compounds have been evaluated for cytotoxicity against four cancer cell lines and one normal cell line. Based on the results, all the tested compounds exhibit moderate to significant cytotoxicity against all the tested cancer cell lines with IC50 values between the 17.3 – 88.8 µM ranges. Among all the tested compounds long chain saturated palmitic and stearic acid derivatives 6g, 6hexhibitsignificantcytotoxicity against cervical cancer cell line with IC50 values 17.3 and 20.3 µM respectively. Moreover, all the tested compounds do not show any toxicity towards normal cell line