Synthesis and antiviral activity of novel spirocyclic nucleosides

Alexander John Andre Cobb; Antonio Dell’Isola; Ban Abdulsattar; Matthew McLachlan; Benjamin Neuman; Christin Muller; Kenneth Shankland; Hawaa  Al-Mulla; Alexander Binks; Warren Elvidge

Synthesis and antiviral activity of novel spirocyclic nucleosides

Alexander John Andre Cobb, Antonio Dell’Isola, Ban Abdulsattar, Matthew McLachlan, Benjamin Neuman, Christin Muller, Kenneth Shankland, Hawaa Al-Mulla, Alexander Binks, Warren Elvidge

Chemistry

Research output: Contribution to journal › Review article › peer-review

14 Citations (Scopus)

Abstract

The synthesis of a number of spirocyclic ribonucleosides containing either a triazolic or azetidinic system is described, along with two analogous phosphonate derivatives of the former. These systems were constructed from the same b-D-psicofuranose starting material. The triazole spirocyclic nucleosides were constructed using the 1-azido-1-hydroxymethyl derived sugars, where the primary alcohol was alkylated with a range of propargyl bromides, whereas the azetidine systems orginated from the corresponding 1-cyano-1-hydroxymethyl sugars. Owing to their close similarity with ribavirin, the library of compounds were investigated for their antiviral properties using MHV (Murine Hepatitis Virus) as a model.

Original language	English
Article number	c8nj02777c
Pages (from-to)	18363-18380
Number of pages	7
Journal	NEW JOURNAL OF CHEMISTRY
Volume	42
Publication status	Published - 13 Oct 2018

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https://pubs.rsc.org/en/content/articlepdf/2018/nj/c8nj02777c

14 Citations
1 Article

Synthesis and Antiviral Properties of Spirocyclic [1,2,3]-Triazolooxazine Nucleosides
Dell'Isola, A., McLachlan, M. M. W., Neuman, B. W., Al-Mullah, H. M. N., Binks, A. W. D., Elvidge, W., Shankland, K. & Cobb, A. J. A., 8 Sept 2014, In: CHEMISTRY. 20, 37, p. 11685-11689
Research output: Contribution to journal › Article › peer-review
27 Citations (Scopus)

Cite this

@article{7c77fa5cda7a4e12a2e4f405b57984a3,

title = "Synthesis and antiviral activity of novel spirocyclic nucleosides",

abstract = "The synthesis of a number of spirocyclic ribonucleosides containing either a triazolic or azetidinic system is described, along with two analogous phosphonate derivatives of the former. These systems were constructed from the same b-D-psicofuranose starting material. The triazole spirocyclic nucleosides were constructed using the 1-azido-1-hydroxymethyl derived sugars, where the primary alcohol was alkylated with a range of propargyl bromides, whereas the azetidine systems orginated from the corresponding 1-cyano-1-hydroxymethyl sugars. Owing to their close similarity with ribavirin, the library of compounds were investigated for their antiviral properties using MHV (Murine Hepatitis Virus) as a model.",

author = "Cobb, {Alexander John Andre} and Antonio Dell{\textquoteright}Isola and Ban Abdulsattar and Matthew McLachlan and Benjamin Neuman and Christin Muller and Kenneth Shankland and Hawaa Al-Mulla and Alexander Binks and Warren Elvidge",

year = "2018",

month = oct,

day = "13",

language = "English",

volume = "42",

pages = "18363--18380",

journal = "NEW JOURNAL OF CHEMISTRY",

issn = "1144-0546",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Synthesis and antiviral activity of novel spirocyclic nucleosides

AU - Cobb, Alexander John Andre

AU - Dell’Isola, Antonio

AU - Abdulsattar, Ban

AU - McLachlan, Matthew

AU - Neuman, Benjamin

AU - Muller, Christin

AU - Shankland, Kenneth

AU - Al-Mulla, Hawaa

AU - Binks, Alexander

AU - Elvidge, Warren

PY - 2018/10/13

Y1 - 2018/10/13

N2 - The synthesis of a number of spirocyclic ribonucleosides containing either a triazolic or azetidinic system is described, along with two analogous phosphonate derivatives of the former. These systems were constructed from the same b-D-psicofuranose starting material. The triazole spirocyclic nucleosides were constructed using the 1-azido-1-hydroxymethyl derived sugars, where the primary alcohol was alkylated with a range of propargyl bromides, whereas the azetidine systems orginated from the corresponding 1-cyano-1-hydroxymethyl sugars. Owing to their close similarity with ribavirin, the library of compounds were investigated for their antiviral properties using MHV (Murine Hepatitis Virus) as a model.

AB - The synthesis of a number of spirocyclic ribonucleosides containing either a triazolic or azetidinic system is described, along with two analogous phosphonate derivatives of the former. These systems were constructed from the same b-D-psicofuranose starting material. The triazole spirocyclic nucleosides were constructed using the 1-azido-1-hydroxymethyl derived sugars, where the primary alcohol was alkylated with a range of propargyl bromides, whereas the azetidine systems orginated from the corresponding 1-cyano-1-hydroxymethyl sugars. Owing to their close similarity with ribavirin, the library of compounds were investigated for their antiviral properties using MHV (Murine Hepatitis Virus) as a model.

M3 - Review article

SN - 1144-0546

VL - 42

SP - 18363

EP - 18380

JO - NEW JOURNAL OF CHEMISTRY

JF - NEW JOURNAL OF CHEMISTRY

M1 - c8nj02777c

ER -

Synthesis and antiviral activity of novel spirocyclic nucleosides

Abstract

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Research output

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

Cite this