Synthesis of 1,2,3-triazolylpyranosides through click chemistry reaction

We have developed an efficient method for the synthesis of functionalized C-glycosyl 1,2,3-triazoles through a Cu(1)-promoted azide-alkyne 1,3-dipolar cycloaddition between a TMS-protected C-alkynyl-glycoside and organic azides. The reaction was accelerated by ultrasound irradiation and the addition of a base was not necessary to obtain the 1,2,3-triazole product. Moreover, further manipulation of the products led to chiral molecules with a C-glycoside linkage. (C) 2012 Elsevier Ltd. All rights reserved.

On the search for potential anti-Trypanosoma cruzi drugs: Synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions

Five 2-hydroxy-3-substituted-aminomethyl naphthoquinones, nine 1,2,3-triazolic para-naphthoquinones, five nor-beta-lapachone-based 1,2,3-triazoles, and several other naphthoquinonoid compounds were synthesized and evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease, continuing our screening program for new trypanocidal compounds. Among all the substances, 16-18, 23, 25-29 and 30-33 were herein described for the first time and fifteen substances were identified as more potent than the standard drug benznidazole, with IC50/24 h values in the range of 10.9-101.5 mu M. Compounds 14 and 19 with Selectivity Index of 18.9 and 6.1 are important structures for further studies. (C) 2012 Elsevier Masson SAS. All rights reserved.