Synthetic approach to novel glycosyltriazole-3-hydroxyquinolone conjugates and their antimicrobial properties
Abstract
A synthetic approach to novel 2-(1-glycosyl-1,2,3-triazol-4-yl)-3-hydroxyquinolone conjugates has been developed. The methodology involves preparation of a suitable quinoline intermediate and its subsequent conjugation with various acylated glycosyl azides by CuAAC click reaction. A choice of protective group at quinoline moiety appeared to be crucial for subsequent 3-step deprotection sequence that has to kept glycosyl triazole bond intact. Evaluation of antimicrobial properties of the conjugates revealed that their activity was strongly affected by protecting group of the quinoline moiety. Some of the conjugates inhibited exclusively G+ bacterial strains including honeybee larval pathogen Paenibacillus larvae, which were most susceptible to 2-substituted, particularly 2-glycosylated, dibenzylated quinolines.
- Publication:
-
Journal of Molecular Structure
- Pub Date:
- February 2019
- DOI:
- 10.1016/j.molstruc.2018.09.030
- Bibcode:
- 2019JMoSt1177...16S
- Keywords:
-
- Quinolones;
- Triazole;
- Click-reaction;
- Glycoconjugates;
- Antibacterial