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

doi:10.3390/molecules17010179

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

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

Jamal Krim^1,2, Moha Taourirte¹ and Joachim W. Engels^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; in revised form: 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

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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.

AMA Style

Krim J, Taourirte M, Engels JW. 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(1):179-190.

Chicago/Turabian Style

Krim, Jamal; Taourirte, Moha; Engels, Joachim W. 2012. "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 17, no. 1: 179-190.

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