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

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

1,2, 1 and 2,*
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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