Synthesis 2017; 49(09): 1993-2002
DOI: 10.1055/s-0036-1588409
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of C-Ribosyl-1,2,3-triazolyl Carboxamides

Carmen Solarte
a   Laboratoire de Chimie Biologique, University of Cergy-Pontoise, 5 mail Gay-Lussac, 95031 Cergy-Pontoise Cedex, France   Email: nadege.lubin-germain@u-cergy.fr
,
Michaël Dos Santos
a   Laboratoire de Chimie Biologique, University of Cergy-Pontoise, 5 mail Gay-Lussac, 95031 Cergy-Pontoise Cedex, France   Email: nadege.lubin-germain@u-cergy.fr
,
Simon Gonzalez
a   Laboratoire de Chimie Biologique, University of Cergy-Pontoise, 5 mail Gay-Lussac, 95031 Cergy-Pontoise Cedex, France   Email: nadege.lubin-germain@u-cergy.fr
,
Leandro S. M. Miranda
b   BOSS Laboratory, Federal University of Rio de Janeiro, Av Athos da Silveira Ramos149, 21941909 Ilha do Fundão, Rio de Janeiro, Brazil
,
Régis Guillot
c   ICMMO, University of Paris Sud, 15, rue Georges Clémenceau, 91405 Orsay, France
,
Angélique Ferry
a   Laboratoire de Chimie Biologique, University of Cergy-Pontoise, 5 mail Gay-Lussac, 95031 Cergy-Pontoise Cedex, France   Email: nadege.lubin-germain@u-cergy.fr
,
Florian Gallier
a   Laboratoire de Chimie Biologique, University of Cergy-Pontoise, 5 mail Gay-Lussac, 95031 Cergy-Pontoise Cedex, France   Email: nadege.lubin-germain@u-cergy.fr
,
Jacques Uziel
a   Laboratoire de Chimie Biologique, University of Cergy-Pontoise, 5 mail Gay-Lussac, 95031 Cergy-Pontoise Cedex, France   Email: nadege.lubin-germain@u-cergy.fr
,
Nadège Lubin-Germain*
a   Laboratoire de Chimie Biologique, University of Cergy-Pontoise, 5 mail Gay-Lussac, 95031 Cergy-Pontoise Cedex, France   Email: nadege.lubin-germain@u-cergy.fr
› Author Affiliations
Further Information

Publication History

Received: 16 November 2016

Accepted after revision: 13 January 2017

Publication Date:
07 February 2017 (online)


Abstract

Because of the emergence of new viruses, the need for new antiviral broad-spectrum compounds remains important. In this context, herein the synthesis of C-nucleosides, structurally close to ribavirin, a nucleoside presenting various biological activities and used until now particularly for its broad-spectrum antiviral properties, is reported. The compounds were designed in order to increase their stability and the number of hydrogen bond donor or acceptor in comparison to ribavirin, and to investigate the role of the carboxamide group on the biological activity. The efficient synthesis of 11 C-nucleosides is based on an indium-mediated alkynylglycosylation as the key step, followed by the construction of the triazole heterocycle. Amidation was performed with primary and secondary amines in yields up to 85%. An analogue nucleoside with a triazole without carboxamide group was also prepared in order to compare its activity. Finally, the carboxamide group was moved to the N-1 triazole position to mimic ribavirin.

Supporting Information

 
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