Synthesis, Characterization and Antibacterial Activity of Surfactants Containing Alkyl-Sugar 1,4-Disubstituted Triazoles

Abstract

Two surfactants containing alkyl-sugar 1,4-disubstituted triazoles glycoconjugates were synthesized via Cu(I) catalyzed click conditions between azido alkane(C7,C8) and D-mannose based bis –O- propynyl ether. The latter was prepared via Williamson etherification between propargyl bromide and the2C-branched-D-mannose diacetonide which was synthesized in a previous work by aldol condensation between formaldehyde and the protected sugar in MeOH. The two surfactants have been examined in vitro by inhibition of bacteria growth ( Escherichia coli and staphylococcus aureus)  and showed a moderate activity. The two prepared surfactants were purified by column chromatography and identified by TLC, FTIR, ¹HNMR , ¹³CNMR, 2D-NMR  correlation COSY and HSQC.