| Publication Type |
Journal Article |
| Title |
Synthesis of sugars embodying conjugated carbonyl systems and related triazole derivatives from carboxymethyl glycoside lactones. Evaluation of their antimicrobial activity and toxicity |
| Authors |
Nuno Manuel Xavier Margarida Goulart Ana Neves Jorge Justino Stephane Chambert Amélia P. Rauter Y. Queneau |
| Groups |
HC |
| Journal |
BIOORGANIC \& MEDICINAL CHEMISTRY |
| Year |
2011 |
| Month |
January |
| Volume |
19 |
| Number |
2 |
| Pages |
926-938 |
| Abstract |
The synthesis of a series of pyranoid derivatives comprising a conjugated carbonyl function and related triazole derivatives, structurally suitable for bioactivity evaluation, was achieved in few steps starting from readily available carboxymethyl glycoside lactones (CMGL). 3-Enopyranosid-2-uloses were generated by oxidation/elimination of tri-O-acylated 2-hydroxy pyranosides. Subsequent Wittig olefination provided stereoselectively 2-C-branched-chain conjugated dienepyranosides with (E)-configuration around the exocyclic double bond. A heterogeneous CuI/Amberlyst-catalyzed click chemistry protocol was used to convert glycosides bearing a propargyl moiety into the corresponding 1,2,3-triazoles. These new molecules were screened for their in vitro antibacterial and antifungal activities and those containing conjugated carbonyl systems demonstrated the best efficacy. (N-Dodecylcarbamoyl)methyl enone glycerosides were the most active ones among the enones tested. The alpha-anomer displayed very strong activities against Bacillus cereus and Bacillus subtilis and strong activity toward Enterococcus faecalis and the fungal pathogen Penicillium aurantiogriseum. The corresponding beta-anomer presented a very strong inhibitory effect against two fungal species (Aspergillus niger and P. aurantiogriseum). (N-Dodecyl-/N-propargyl/or N-benzylcarbamoyl) methyl dienepyranosides exhibited selectively a strong activity toward E. faecalis. Further acute toxicity evaluation indicated low toxic effect of the (N-dodecylcarbamoyl)methyl enone glyceroside alpha-anomer and of the carbamoylmethyl dienepyranosides N-protected with propargyl or benzyl groups. (C) 2010 Elsevier Ltd. All rights reserved. |
| DOI |
http://dx.doi.org/10.1016/j.bmc.2010.11.060 |
| ISBN |
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| Publisher |
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| Book Title |
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| ISSN |
0968-0896 |
| EISSN |
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| Conference Name |
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| Bibtex ID |
ISI:000287590500023 |
| Observations |
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