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Norbornane-based nucleoside and nucleotide analogues locked in North conformation

We report on the synthesis of novel conformationally locked nucleoside and nucleotide derivatives, which are structurally closely related to clinically used antivirals such as didanosine and abacavir. As a suitable conformationally rigid substitute of the sugar/pseudosugar ring allowing a permanent... Full description

Journal Title: Bioorganic & Medicinal Chemistry 01 January 2015, Vol.23(1), pp.184-191
Main Author: Dejmek, Milan
Other Authors: Šála, Michal , Hřebabecký, Hubert , Dračínský, Martin , Procházková, Eliška , Chalupská, Dominika , Klíma, Martin , Plačková, Pavla
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0968-0896 ; E-ISSN: 1464-3391 ; DOI: 10.1016/j.bmc.2014.11.011
Link: https://www.sciencedirect.com/science/article/pii/S0968089614007986
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recordid: elsevier_sdoi_10_1016_j_bmc_2014_11_011
title: Norbornane-based nucleoside and nucleotide analogues locked in North conformation
format: Article
creator:
  • Dejmek, Milan
  • Šála, Michal
  • Hřebabecký, Hubert
  • Dračínský, Martin
  • Procházková, Eliška
  • Chalupská, Dominika
  • Klíma, Martin
  • Plačková, Pavla
subjects:
  • Carbocyclic Nucleosides
  • Purines
  • Norbornane
  • Antiviral
  • Pi4kiiα
  • Medicine
  • Chemistry
  • Anatomy & Physiology
ispartof: Bioorganic & Medicinal Chemistry, 01 January 2015, Vol.23(1), pp.184-191
description: We report on the synthesis of novel conformationally locked nucleoside and nucleotide derivatives, which are structurally closely related to clinically used antivirals such as didanosine and abacavir. As a suitable conformationally rigid substitute of the sugar/pseudosugar ring allowing a permanent stabilization of the nucleoside in North conformation we employed bicyclo[2.2.1]heptane (norbornane) substituted in the bridgehead position with a hydroxymethyl group and in the C-3 position with a nucleobase. Prepared nucleoside derivatives were also converted into appropriate phosphoramidate prodrugs (ProTides) in order to increase delivery of the compounds in the cells. All target compounds were evaluated in a broad antiviral and cytostatic assay panel.
language: eng
source:
identifier: ISSN: 0968-0896 ; E-ISSN: 1464-3391 ; DOI: 10.1016/j.bmc.2014.11.011
fulltext: fulltext
issn:
  • 0968-0896
  • 09680896
  • 1464-3391
  • 14643391
url: Link


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creatorDejmek, Milan ; Šála, Michal ; Hřebabecký, Hubert ; Dračínský, Martin ; Procházková, Eliška ; Chalupská, Dominika ; Klíma, Martin ; Plačková, Pavla
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descriptionWe report on the synthesis of novel conformationally locked nucleoside and nucleotide derivatives, which are structurally closely related to clinically used antivirals such as didanosine and abacavir. As a suitable conformationally rigid substitute of the sugar/pseudosugar ring allowing a permanent stabilization of the nucleoside in North conformation we employed bicyclo[2.2.1]heptane (norbornane) substituted in the bridgehead position with a hydroxymethyl group and in the C-3 position with a nucleobase. Prepared nucleoside derivatives were also converted into appropriate phosphoramidate prodrugs (ProTides) in order to increase delivery of the compounds in the cells. All target compounds were evaluated in a broad antiviral and cytostatic assay panel.
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titleNorbornane-based nucleoside and nucleotide analogues locked in North conformation
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We report on the synthesis of novel conformationally locked nucleoside and nucleotide derivatives, which are structurally closely related to clinically used antivirals such as didanosine and abacavir. As a suitable conformationally rigid substitute of the sugar/pseudosugar ring allowing a permanent stabilization of the nucleoside in North conformation we employed bicyclo[2.2.1]heptane (norbornane) substituted in the bridgehead position with a hydroxymethyl group and in the C-3 position with a nucleobase. Prepared nucleoside derivatives were also converted into appropriate phosphoramidate prodrugs (ProTides) in order to increase delivery of the compounds in the cells. All target compounds were evaluated in a broad antiviral and cytostatic assay panel.

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We report on the synthesis of novel conformationally locked nucleoside and nucleotide derivatives, which are structurally closely related to clinically used antivirals such as didanosine and abacavir. As a suitable conformationally rigid substitute of the sugar/pseudosugar ring allowing a permanent stabilization of the nucleoside in North conformation we employed bicyclo[2.2.1]heptane (norbornane) substituted in the bridgehead position with a hydroxymethyl group and in the C-3 position with a nucleobase. Prepared nucleoside derivatives were also converted into appropriate phosphoramidate prodrugs (ProTides) in order to increase delivery of the compounds in the cells. All target compounds were evaluated in a broad antiviral and cytostatic assay panel.

pubElsevier Ltd
doi10.1016/j.bmc.2014.11.011
lad01Bioorganic & Medicinal Chemistry
date2015-01-01