Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y(2) Receptor Ligand

In this study we report the synthesis of C5/C6-fused uridine phosphonates that are structurally related to earlier reported allosteric P2Y(2) receptor ligands. A silyl-Hilbert-Johnson reaction of six quinazoline-2,4-(1H,3H)-dione-like base moieties with a suitable ribofuranosephosphonate afforded th...

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Detalles Bibliográficos
Autores principales: Song, Lijun, Risseeuw, Martijn D. P., Karalic, Izet, Barrett, Matthew O., Brown, Kyle A., Harden, T. Kendall, Van Calenbergh, Serge
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270895/
https://www.ncbi.nlm.nih.gov/pubmed/24714193
http://dx.doi.org/10.3390/molecules19044313
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author Song, Lijun
Risseeuw, Martijn D. P.
Karalic, Izet
Barrett, Matthew O.
Brown, Kyle A.
Harden, T. Kendall
Van Calenbergh, Serge
author_facet Song, Lijun
Risseeuw, Martijn D. P.
Karalic, Izet
Barrett, Matthew O.
Brown, Kyle A.
Harden, T. Kendall
Van Calenbergh, Serge
author_sort Song, Lijun
collection PubMed
description In this study we report the synthesis of C5/C6-fused uridine phosphonates that are structurally related to earlier reported allosteric P2Y(2) receptor ligands. A silyl-Hilbert-Johnson reaction of six quinazoline-2,4-(1H,3H)-dione-like base moieties with a suitable ribofuranosephosphonate afforded the desired analogues after full deprotection. In contrast to the parent 5-(4-fluoropheny)uridine phosphonate, the present extended-base uridine phosphonates essentially failed to modulate the P2Y(2) receptor.
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spelling pubmed-62708952019-01-02 Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y(2) Receptor Ligand Song, Lijun Risseeuw, Martijn D. P. Karalic, Izet Barrett, Matthew O. Brown, Kyle A. Harden, T. Kendall Van Calenbergh, Serge Molecules Article In this study we report the synthesis of C5/C6-fused uridine phosphonates that are structurally related to earlier reported allosteric P2Y(2) receptor ligands. A silyl-Hilbert-Johnson reaction of six quinazoline-2,4-(1H,3H)-dione-like base moieties with a suitable ribofuranosephosphonate afforded the desired analogues after full deprotection. In contrast to the parent 5-(4-fluoropheny)uridine phosphonate, the present extended-base uridine phosphonates essentially failed to modulate the P2Y(2) receptor. MDPI 2014-04-04 /pmc/articles/PMC6270895/ /pubmed/24714193 http://dx.doi.org/10.3390/molecules19044313 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Song, Lijun
Risseeuw, Martijn D. P.
Karalic, Izet
Barrett, Matthew O.
Brown, Kyle A.
Harden, T. Kendall
Van Calenbergh, Serge
Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y(2) Receptor Ligand
title Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y(2) Receptor Ligand
title_full Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y(2) Receptor Ligand
title_fullStr Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y(2) Receptor Ligand
title_full_unstemmed Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y(2) Receptor Ligand
title_short Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y(2) Receptor Ligand
title_sort synthesis of extended uridine phosphonates derived from an allosteric p2y(2) receptor ligand
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270895/
https://www.ncbi.nlm.nih.gov/pubmed/24714193
http://dx.doi.org/10.3390/molecules19044313
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