Preparation of 1,4-disubstituted-1,2,3-triazolo ribonucleosides by Na2CuP2O7 catalyzed azide-alkyne 1,3-dipolar cycloaddition
Hanane Elayadi,a Mohamed Mesnaoui,b Brent E. Korba,c Michael Smietana,d
Jean Jacques Vasseur,d John A. Secrist,e and Hassan B. Lazrek a*
a Unité de Chimie Biomoléculaire et Médicinale, Laboratoire de Chimie Biomoléculaire Substances Naturelles et Réactivité (URAC 16). Faculty of Science Semlalia, Marrakech, Morocco
bLaboratoire de la matière condensée et Environnementale, Faculty of Science Semlalia, Marrakech, Morocco
cDept. of Microbiology and Immunology, Georgetown University Medical Center, Washington, DC 20057, USA
dInstitut des Biomolécules Max Mousseron UMR 5247 CNRS-UMI-UMII, Université Montpellier II, CC008, Place E. Bataillon 34095, Montpellier Cedex 5 France
e Southern Research Institute P.O. Box 55305, Birmingham, Alabama 35255
E-mail:
[email protected]
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Abstract
In this study, we describe the synthesis of 1,4-disustituted-1,2,3-triazolo-ribonucleosides by means of 1,3-dipolar cycloaddition between various N-1 propargyl-pyrimidines and 1’-azido- 2’,3’,5’-tri-O-benzoylribose catalyzed by Na2CuP2O7/sodium ascorbate. All obtained compounds were evaluated for their anti-HCV activity in vitro.
Keywords: 1,2,3-Triazolo ribonucleosides, Na2CuP2O7, click chemistry
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Introduction
Triazole derivatives occupy a prominent place in medicinal chemistry because of their therapeutic properties. Compounds containing a triazole moiety have found tremendous application in the field of pharmaceutical,1 biology,2 and material sciences.3 On the other hand, triazole nucleosides such as Ribavirine (Virazole) or 1,2,3-triazole TSAO analogues are used for the treatment of HCV and HIV4,5 respectively. Thus, the pharmaceutical importance of triazoles has prompted the design and synthesis of various triazolonucleosides.6-7 We previously reported the preparation of various 1,2,3-triazole acyclonucleosides from the propargylated nucleobases by copper-free Huisgen 1,3-dipolar cycloaddition at high temperature and long duration and the
