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Molecules 2012, 17(1), 179-190; doi:10.3390/molecules17010179

Synthesis of 1,4-Disubstituted Mono and Bis-triazolocarbo-acyclonucleoside Analogues of 9-(4-Hydroxybutyl)guanine by Cu(I)-Catalyzed Click Azide-Alkyne Cycloaddition

1
Laboratoire de Chimie Bioorganique et Macromoléculaire, Faculté des Sciences et Techniques - Guéliz, 40000, Marrakech, Maroc
2
Institut für Organische Chemie und Chemische Biologie, J.W. Goethe Universität, Max-von-Laue Str. 7, 60438 Frankfurt am Main, Germany
*
Author to whom correspondence should be addressed.
Received: 16 November 2011 / Revised: 9 December 2011 / Accepted: 19 December 2011 / Published: 27 December 2011
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A series of novel mono-1,2,3-triazole and bis-1,2,3-triazole acyclonucleoside analogues of 9-(4-hydroxybutyl)guanine was prepared via copper(I)-catalyzed 1,3-dipolar cycloaddition of N-9 propargylpurine, N-1-propargylpyrimidines/as-triazine with the azido-pseudo-sugar 4-azidobutylacetate under solvent-free microwave conditions, followed by treatment with K2CO3/MeOH, or NH3/MeOH. All compounds studied in this work were screened for their antiviral activities [against human rhinovirus (HRV) and hepatitis C virus (HCV)] and antibacterial activities against a series of Gram positive and negative bacteria.
Keywords: 1,3-dipolar cycloaddition; 1,2,3 triazole; 1,2,3-bis-triazoles; click azide-alkyne; microwave-assisted synthesis; antibacterial activities 1,3-dipolar cycloaddition; 1,2,3 triazole; 1,2,3-bis-triazoles; click azide-alkyne; microwave-assisted synthesis; antibacterial activities
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Krim, J.; Taourirte, M.; Engels, J.W. Synthesis of 1,4-Disubstituted Mono and Bis-triazolocarbo-acyclonucleoside Analogues of 9-(4-Hydroxybutyl)guanine by Cu(I)-Catalyzed Click Azide-Alkyne Cycloaddition. Molecules 2012, 17, 179-190.

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