Affiliation:
1. Laboratory of Synthesis Heterocyclic and Natural Substances, Faculty of Sciences of Monastir, , Boulevard of Environment, 5000 Monastir,Tunisia
Abstract
Aims:
We have developed this work to recommend an original route for the preparation of triazole derivatives.
Background:
Carbohydrates containing 1,2,3-triazole derivatives have various biological activities. Due to their
advantageous and biological property, they are eye-catching synthetic targets in the arsenal of organic chemistry.
Thus, finding green and efficient methods, as well as using the ball milling procedure for the synthesis of these
heterocycles, is of interest to organic chemistry researchers.
Objective:
The objective of this study was to synthesize carbohydrate-derived triazoles under high-speed vibration
milling conditions and investigate their properties.
Materials and Method:
A mixture of glycoside azide derivatives (1 mmol) and prop-2-yn-1-ol (1.5 mmol) in
the presence of copper (I) was vigorously shaken under vibration milling conditions at 650 rpm with three balls
for 15 min. The deprotection of the resulting triazole derivatives was affected by treatment with 4M hydrochloric
acid in methanol under reflux.
Results and Discussion:
A short and convenient route to synthesize carbohydrate-derived triazoles, based on a
ball-mill via 1,3-dipolar cycloaddition reactions to prop-2-yn-1-ol, was developed. Cleavage of the isopropylidene
protecting group provided water-soluble triazoles, evaluated as glycogen phosphorylase inhibitors. 1-[6-
(4-Hydroxymethyl-[1,2,3]triazol-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-ethane-1,2-diol was
the best inhibitor of rabbit muscle glycogen phosphorylase b (IC50 = 60 μM).
Conclusion:
In summary, we developed new, short and convenient routes to glucose-derived 1,2,3-triazole based
on 1,3-dipolar cycloaddition reactions flowed by ball milling. The use of isopropylidene protective groups gave
access to the analogous deprotected water-soluble motifs, analogous to known inhibitors of glycogen phosphorylase.
Publisher
Bentham Science Publishers Ltd.
Subject
Organic Chemistry,Biochemistry
Cited by
2 articles.
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