Synthesis of (+/-)-1,2,3-triazolo-3 `-deoxy-4 `-hydroxymethyl carbanucleosides via `click' cycloaddition

Julie Broggi; Nicolas Joubert; Silvia Diez-Gonzalez; Sabine Berteina-Raboin; Thomas Zevaco; Steven Patrick Nolan; Luigi A. Agrofoglio

doi:10.1016/j.tet.2008.11.065

Synthesis of (+/-)-1,2,3-triazolo-3 `-deoxy-4 `-hydroxymethyl carbanucleosides via `click' cycloaddition

Julie Broggi, Nicolas Joubert, Silvia Diez-Gonzalez, Sabine Berteina-Raboin, Thomas Zevaco, Steven Patrick Nolan, Luigi A. Agrofoglio

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	1162-1170
Number of pages	9
Journal	Tetrahedron
Volume	65
Issue number	6
DOIs	https://doi.org/10.1016/j.tet.2008.11.065
Publication status	Published - 7 Feb 2009

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

CARBOCYCLIC NUCLEOSIDES
POXVIRUS INFECTIONS
ANTIVIRAL ACTIVITY
TERMINAL ALKYNES
1,3-DIPOLAR CYCLOADDITION
ANTIBACTERIAL ACTIVITY
ANTI-HIV-1 ACTIVITY
CARBONYL-COMPOUNDS
ORTHOPOX VIRUSES
GLYCOSYL AZIDES

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10.1016/j.tet.2008.11.065

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title = "Synthesis of (+/-)-1,2,3-triazolo-3 `-deoxy-4 `-hydroxymethyl carbanucleosides via `click' cycloaddition",

abstract = "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.",

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author = "Julie Broggi and Nicolas Joubert and Silvia Diez-Gonzalez and Sabine Berteina-Raboin and Thomas Zevaco and Nolan, \{Steven Patrick\} and Agrofoglio, \{Luigi A.\}",

year = "2009",

month = feb,

day = "7",

doi = "10.1016/j.tet.2008.11.065",

language = "English",

volume = "65",

pages = "1162--1170",

journal = "Tetrahedron",

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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.

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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 - https://www.scopus.com/pages/publications/58149161540

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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 -

Synthesis of (+/-)-1,2,3-triazolo-3 `-deoxy-4 `-hydroxymethyl carbanucleosides via `click' cycloaddition

Abstract

UN SDGs

Keywords

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