Synthesis and Antiviral Properties of Spirocyclic [1,2,3]-Triazolooxazine Nucleosides

Antonio Dell'Isola; Matthew M. W. McLachlan; Benjamin W. Neuman; Hawaa M. N. Al-Mullah; Alexander W. D. Binks; Warren Elvidge; Kenneth Shankland; Alexander J. A. Cobb

doi:10.1002/chem.201403560

Synthesis and Antiviral Properties of Spirocyclic [1,2,3]-Triazolooxazine Nucleosides

Antonio Dell'Isola, Matthew M. W. McLachlan, Benjamin W. Neuman, Hawaa M. N. Al-Mullah, Alexander W. D. Binks, Warren Elvidge, Kenneth Shankland, Alexander J. A. Cobb

Chemistry

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

27 Citations (Scopus)

Abstract

An efficient synthesis of spirocyclic triazolooxazine nucleosides is described. This was achieved by the conversion of β‐D‐psicofuranose to the corresponding azido‐derivative, followed by alkylation of the primary alcohol with a range of propargyl bromides, obtained by Sonogashira chemistry. The products of these reactions underwent 1,3‐dipolar addition smoothly to generate the protected spirocyclic adducts. These were easily deprotected to give the corresponding ribose nucleosides. The library of compounds obtained was investigated for its antiviral activity using MHV (mouse hepatitis virus) as a model wherein derivative 3 f showed the most promising activity and tolerability.

Original language	English
Pages (from-to)	11685-11689
Journal	CHEMISTRY
Volume	20
Issue number	37
Early online date	31 Jul 2014
DOIs	https://doi.org/10.1002/chem.201403560
Publication status	Published - 8 Sept 2014

Keywords

alkynes
antiviral agents
cycloaddition
nucleosides
spiro compounds

UN SDGs

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

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10.1002/chem.201403560

27 Citations
1 Review article

Synthesis and antiviral activity of novel spirocyclic nucleosides
Cobb, A. J. A., Dell’Isola, A., Abdulsattar, B., McLachlan, M., Neuman, B., Muller, C., Shankland, K., Al-Mulla, H., Binks, A. & Elvidge, W., 13 Oct 2018, In: NEW JOURNAL OF CHEMISTRY. 42, p. 18363-18380 7 p., c8nj02777c.
Research output: Contribution to journal › Review article › peer-review

Cite this

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title = "Synthesis and Antiviral Properties of Spirocyclic [1,2,3]-Triazolooxazine Nucleosides",

abstract = "An efficient synthesis of spirocyclic triazolooxazine nucleosides is described. This was achieved by the conversion of β‐D‐psicofuranose to the corresponding azido‐derivative, followed by alkylation of the primary alcohol with a range of propargyl bromides, obtained by Sonogashira chemistry. The products of these reactions underwent 1,3‐dipolar addition smoothly to generate the protected spirocyclic adducts. These were easily deprotected to give the corresponding ribose nucleosides. The library of compounds obtained was investigated for its antiviral activity using MHV (mouse hepatitis virus) as a model wherein derivative 3 f showed the most promising activity and tolerability.",

keywords = "alkynes, antiviral agents, cycloaddition, nucleosides, spiro compounds",

author = "Antonio Dell'Isola and McLachlan, {Matthew M. W.} and Neuman, {Benjamin W.} and Al-Mullah, {Hawaa M. N.} and Binks, {Alexander W. D.} and Warren Elvidge and Kenneth Shankland and Cobb, {Alexander J. A.}",

year = "2014",

month = sep,

day = "8",

doi = "10.1002/chem.201403560",

language = "English",

volume = "20",

pages = "11685--11689",

journal = "CHEMISTRY",

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TY - JOUR

T1 - Synthesis and Antiviral Properties of Spirocyclic [1,2,3]-Triazolooxazine Nucleosides

AU - Dell'Isola, Antonio

AU - McLachlan, Matthew M. W.

AU - Neuman, Benjamin W.

AU - Al-Mullah, Hawaa M. N.

AU - Binks, Alexander W. D.

AU - Elvidge, Warren

AU - Shankland, Kenneth

AU - Cobb, Alexander J. A.

PY - 2014/9/8

Y1 - 2014/9/8

N2 - An efficient synthesis of spirocyclic triazolooxazine nucleosides is described. This was achieved by the conversion of β‐D‐psicofuranose to the corresponding azido‐derivative, followed by alkylation of the primary alcohol with a range of propargyl bromides, obtained by Sonogashira chemistry. The products of these reactions underwent 1,3‐dipolar addition smoothly to generate the protected spirocyclic adducts. These were easily deprotected to give the corresponding ribose nucleosides. The library of compounds obtained was investigated for its antiviral activity using MHV (mouse hepatitis virus) as a model wherein derivative 3 f showed the most promising activity and tolerability.

AB - An efficient synthesis of spirocyclic triazolooxazine nucleosides is described. This was achieved by the conversion of β‐D‐psicofuranose to the corresponding azido‐derivative, followed by alkylation of the primary alcohol with a range of propargyl bromides, obtained by Sonogashira chemistry. The products of these reactions underwent 1,3‐dipolar addition smoothly to generate the protected spirocyclic adducts. These were easily deprotected to give the corresponding ribose nucleosides. The library of compounds obtained was investigated for its antiviral activity using MHV (mouse hepatitis virus) as a model wherein derivative 3 f showed the most promising activity and tolerability.

KW - alkynes

KW - antiviral agents

KW - cycloaddition

KW - nucleosides

KW - spiro compounds

U2 - 10.1002/chem.201403560

DO - 10.1002/chem.201403560

M3 - Article

SN - 0947-6539

VL - 20

SP - 11685

EP - 11689

JO - CHEMISTRY

JF - CHEMISTRY

IS - 37

ER -

Synthesis and Antiviral Properties of Spirocyclic [1,2,3]-Triazolooxazine Nucleosides

Abstract

Keywords

UN SDGs

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Research output

Synthesis and antiviral activity of novel spirocyclic nucleosides

Cite this