Synthesis and antitumor activity of N-substituted-β-D-glucosamine derivatives
Seventeen novel N-substituted-β-D-glucosamine derivatives that incorporate benzenesulfonamides with 1,2,3-triazole were synthesized using a bioisosterism strategy.Each derivative was evaluated in vitro for its inhibitory activity against human carbonic anhydrase Ⅸ and tumor cytotoxicity against HCT116 cell line.Moreover,the calculated LogP(cLogP)values showed that all the compounds tended to be hydrophilic.In addition,topological polar surface area(TPSA)value-based predictions highlighted the selectivity of membrane-associated CA Ⅸ.A total of 17 target compounds were synthesized,and their structures were confirmed by MS,1H-NMR and 13C-NMR spectra.In vitro activity tests showed that compounds 14b(IC50=18.69 μmol·L-1)and 14c(IC50=21.25 µmol·L-1)had the best HCT116 cell inhibitory activity.
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