1269663-97-9Relevant academic research and scientific papers
Synthesis and use of new C-glycosyl bicyclic lactones
Listkowski, Arkadiusz,Otman, Otman,Chambert, Stéphane,Queneau, Yves
, p. 5051 - 5053 (2015)
Abstract New C-glycosyl bicyclic lactones have been synthesized in three steps from glycosyl bromides and used as synthons towards C-glycosyl derivatives which can readily be elaborated to 1,2-bisfunctionalized carbohydrate systems. The method was illustrated with several examples of pseudo conjugates prepared from the new C-glycosyl 1,2-fused pyrano-δ-lactonic building blocks, either with groups such as allyl or propargyl with wide subsequent reactivity, or with more elaborated moieties leading to model glycoaminoacids or pseudo nucleotide sugars.
Synthesis of sugars embodying conjugated carbonyl systems and related triazole derivatives from carboxymethyl glycoside lactones. Evaluation of their antimicrobial activity and toxicity
Xavier, Nuno M.,Goulart, Margarida,Neves, Ana,Justino, Jorge,Chambert, Stéphane,Rauter, Amélia P.,Queneau, Yves
experimental part, p. 926 - 938 (2011/03/18)
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 α-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 β-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 α-anomer and of the carbamoylmethyl dienepyranosides N-protected with propargyl or benzyl groups.
