Preparation and reactions of sugar azides with alkynes: synthesis of sugar triazoles as antitubercular agents

Synthesis of 1,2,3-Triazole 5-Chloroisatin Derivatives via Copper-Catalyzed 1,3-Dipolar Cycloaddition Reactions

“…In fact, the orthogonal character vs. the reactivity of most functional groups, complete regioselectivity in favor of the 1,4-disustituted-1,2,3-triazole, mild reaction conditions, and easy installation of the required azide and terminal alkyne moieties in the reactive partners, render the metal-promoted version of the long-standing Huisgen 1,3-dipolar cycloaddition reaction the most prominent technique in the clickchemistry toolbox [9]. With applications ranging from material science to medicinal chemistry the 1,2,3-triazole core has been recognized as one of the most potent azoles with broad chemotherapeutic properties including antifungal [10], anticancer [11], antitubercular [12], antimalarial [13], anti-inflammatory [14], and antiviral [15] activities. Isatin and its derivatives are currently being considered as an important class of molecules, since many of them show diverse biological activities such as antiviral, anticancer [16][17][18][19], antibacterial [20,21] and anticorrosive [22,23] ones [24].…”

Antimicrobial and cytotoxic activities of 1,2,3-triazole-sucrose derivatives

“…Others were tested against fucosidases, 15 trans-sialidase, 16 glycogen phosphorylase, 17 etc. Members of the sugar-triazole conjugates family were investigated for other biological activities, such as receptor interactions, 18 antitubercular activity, 19 nucleoside mimetics, 20 and antiviral agents. 21 Many of them have shown strong antibacterial and antifungal activities, for example glycal-derived tetrahydrofuran 1,2,3-triazoles, 22 pyranoid derivatives comprising both triazole and conjugated carbonyl system, 23 d-glucose-derived benzyl and alkyl 1,2,3-triazoles, 24 6-triazolyl 2,3,6-trideoxy sugars, 25 and triazoles with substituted triazole-piperidine side chains.…”

A mild and efficient method for preparation of azides from alcohols using acidic ionic liquid [H-NMP]HSO4

“…9,2f Azides have been used for preparation of medicines such as azido pyrimidines and purines due to their anti HIV-1 biological activity, 10 also 5-azido-5-deoxyxylofuranose has been employed for synthesis of sugar triazole derivatives as anti tuberculosis agents. 11 Protic acidic ionic liquids (ILs) have frequently been used as green solvents and catalysts in place of conventional organic solvents and acid catalysts. 12 In continuation of our ongoing projects to develop efficient methods for organic functional groups transformation, [13][14][15] here we wish to report the synthesis and characterization of pyrrolidinium bisulfate [H-NMP]HSO 4 , which is a new acidic ionic liquid, 16 as a highly chemoselective, inexpensive, and efficient catalyst and also as a solvent for conversion of alcohols to the corresponding azides using NaN 3 (Scheme 1).…”