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Synthesis and investigation of antimicrobial activity of 8-hydroxyquinoline glucosaminides

“…Chemical shifts (CS) of the proton signals of the glyco side residues and aglycone parts of the compounds (V)-(VII) corresponded to the values obtained earlier [14][15][16] and literature data [13]. The influence of the neighboring pyridine nucleus on the CS value of the anomeric proton in 8 oxyquinoline glycosides (V)-(VII), which were shifted in the region of the weak field (δ 5.66, 5.72, and 5.73 ppm) in comparison with similar signals in the spectra of aryl glucosamidines [14][15][16] should be noted.…”

“…An effective approach suggested earlier for the aryl β D glucosaminide synthesis by glycosylation of aromatic hydroxyl containing compounds in the phase transfer (PT) catalytic system of solid potassium carbonate anhy drous acetonitrile was used to create O β glycoside link age in compounds (V)-(VII) (scheme) [14][15][16]. The interaction of equimolar amounts of chloride (I), hydroxyl derivatives (II)-(IV) and anhydrous potassium carbonate in the presence of the PT catalyst, 15C5, although it resulted in the target products (V)-(VII), pro vided low yields due to the formation of oxazoline (XI), as well as a series of unidentified products of carbohydrate destruction.…”

“…Full acetates (V)-(VII) were deacetylated according to Zemplen using the method [16,17] to form triols (VIII)-(X). Completeness of the О acetyl protective group removal was assessed by 1 Н NMR spectroscopy (table) and HPLC.…”

Synthesis and Protective Activity of β-Glycosides of N-Acetylmuramyl-L-Alanyl-D-Isoglutamine with Alkylalicyclic and Arylaliphatic Aglycons

“…2 In contrast, the glycosides with predominating lipophylic properties have not been studied methodically. However, some experiments [3,4] indicated that β -hexadecyl MDP [5], β -(2,3-didodecyloxypropyl) MDP [6], and β -cholesteryl MDP [7] activate immune reactions more effectively than MDP itself. A keen interest in lipophilic MDP derivatives is also associated with the fact that ε -octadecanoyl MDP-L -lysine (Romurtid) [8] and phosphatidylethanolamide of MDP-L -alanine [9] are allowed for the therapeutic use.…”

A Phase-Transfer Glucosamination of Phenols Catalyzed by Polyethylene Glycol

“…2 We have previously demonstrated a high efficiency of various CEs for the use in the interphase catalytic processes of glycosylation of aromatic compounds in the solid phase-liquid phase system [2][3][4][5]. A closeness of the chemical nature of oligoethylene glycols and CEs allows one to expect their catalytic activity would be comparable with that of macrocyclic polyethers.…”