TY - JOUR
T1 - Synthesis of (+/-)-1,2,3-triazolo-3 `-deoxy-4 `-hydroxymethyl carbanucleosides via `click' cycloaddition
AU - Broggi, Julie
AU - Joubert, Nicolas
AU - Diez-Gonzalez, Silvia
AU - Berteina-Raboin, Sabine
AU - Zevaco, Thomas
AU - Nolan, Steven Patrick
AU - Agrofoglio, Luigi A.
PY - 2009/2/7
Y1 - 2009/2/7
N2 - The synthesis of 1,2,3-triazolo-3'-deoxy-4'-hydroxymethyl carbanucleosides with different reaction conditions and diverse modulations on the heterocycle residues was developed. Heterocycle moieties were efficiently introduced on the pseudo-sugar either via nucleophilic substitution or via 1,3-dipolar Huisgen cycloaddition. With this latter approach, 1,4-disubstituted and 1,4,5-trisubstituted-(+/-)-[1,2,3]-triazolo-3'-deoxy-4'-hydroxymethyl carbanucleosides were prepared from the corresponding azido-carbocycle and various terminal or internal alkynes. Antiviral activities and cellular toxicities of the final compounds were evaluated as smallpox inhibitors. Unfortunately, at concentrations tip to 100 mM, none of them inhibited production of vaccinia virus (Lister strain) or cowpox Virus (Brighton strain) in vero cells. (C) 2008 Elsevier Ltd. All rights reserved.
AB - The synthesis of 1,2,3-triazolo-3'-deoxy-4'-hydroxymethyl carbanucleosides with different reaction conditions and diverse modulations on the heterocycle residues was developed. Heterocycle moieties were efficiently introduced on the pseudo-sugar either via nucleophilic substitution or via 1,3-dipolar Huisgen cycloaddition. With this latter approach, 1,4-disubstituted and 1,4,5-trisubstituted-(+/-)-[1,2,3]-triazolo-3'-deoxy-4'-hydroxymethyl carbanucleosides were prepared from the corresponding azido-carbocycle and various terminal or internal alkynes. Antiviral activities and cellular toxicities of the final compounds were evaluated as smallpox inhibitors. Unfortunately, at concentrations tip to 100 mM, none of them inhibited production of vaccinia virus (Lister strain) or cowpox Virus (Brighton strain) in vero cells. (C) 2008 Elsevier Ltd. All rights reserved.
KW - CARBOCYCLIC NUCLEOSIDES
KW - POXVIRUS INFECTIONS
KW - ANTIVIRAL ACTIVITY
KW - TERMINAL ALKYNES
KW - 1,3-DIPOLAR CYCLOADDITION
KW - ANTIBACTERIAL ACTIVITY
KW - ANTI-HIV-1 ACTIVITY
KW - CARBONYL-COMPOUNDS
KW - ORTHOPOX VIRUSES
KW - GLYCOSYL AZIDES
UR - http://www.scopus.com/inward/record.url?scp=58149161540&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2008.11.065
DO - 10.1016/j.tet.2008.11.065
M3 - Article
SN - 0040-4020
VL - 65
SP - 1162
EP - 1170
JO - Tetrahedron
JF - Tetrahedron
IS - 6
ER -