Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y2 Receptor Ligand
In this study we report the synthesis of C5/C6-fused uridine phosphonates that are structurally related to earlier reported allosteric P2Y2 receptor ligands. A silyl-Hilbert-Johnson reaction of six quinazoline-2,4-(1H,3H)-dione-like base moieties with a suitable ribofuranosephosphonate afforded the...
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| Format: | Article |
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MDPI AG
2014-04-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/19/4/4313 |
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| author | Lijun Song Martijn D. P. Risseeuw Izet Karalic Matthew O. Barrett Kyle A. Brown T. Kendall Harden Serge Van Calenbergh |
| author_facet | Lijun Song Martijn D. P. Risseeuw Izet Karalic Matthew O. Barrett Kyle A. Brown T. Kendall Harden Serge Van Calenbergh |
| author_sort | Lijun Song |
| collection | DOAJ |
| description | In this study we report the synthesis of C5/C6-fused uridine phosphonates that are structurally related to earlier reported allosteric P2Y2 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 P2Y2 receptor. |
| first_indexed | 2024-12-19T19:50:06Z |
| format | Article |
| id | doaj.art-90bc235eefcf4629b2b6b8d027b90751 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-19T19:50:06Z |
| publishDate | 2014-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-90bc235eefcf4629b2b6b8d027b907512022-12-21T20:08:01ZengMDPI AGMolecules1420-30492014-04-011944313432510.3390/molecules19044313molecules19044313Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y2 Receptor LigandLijun Song0Martijn D. P. Risseeuw1Izet Karalic2Matthew O. Barrett3Kyle A. Brown4T. Kendall Harden5Serge Van Calenbergh6Laboratory for Medicinal Chemistry, Ghent University, Harelbekestraat 72, B-9000 Ghent, BelgiumLaboratory for Medicinal Chemistry, Ghent University, Harelbekestraat 72, B-9000 Ghent, BelgiumLaboratory for Medicinal Chemistry, Ghent University, Harelbekestraat 72, B-9000 Ghent, BelgiumDepartment of Pharmacology, University of North Carolina, School of Medicine, Chapel Hill, NC 27599-7365, USADepartment of Pharmacology, University of North Carolina, School of Medicine, Chapel Hill, NC 27599-7365, USADepartment of Pharmacology, University of North Carolina, School of Medicine, Chapel Hill, NC 27599-7365, USALaboratory for Medicinal Chemistry, Ghent University, Harelbekestraat 72, B-9000 Ghent, BelgiumIn this study we report the synthesis of C5/C6-fused uridine phosphonates that are structurally related to earlier reported allosteric P2Y2 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 P2Y2 receptor.http://www.mdpi.com/1420-3049/19/4/4313nucleoside phosphonatesextended uridineP2Y2 receptor |
| spellingShingle | Lijun Song Martijn D. P. Risseeuw Izet Karalic Matthew O. Barrett Kyle A. Brown T. Kendall Harden Serge Van Calenbergh Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y2 Receptor Ligand Molecules nucleoside phosphonates extended uridine P2Y2 receptor |
| title | Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y2 Receptor Ligand |
| title_full | Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y2 Receptor Ligand |
| title_fullStr | Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y2 Receptor Ligand |
| title_full_unstemmed | Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y2 Receptor Ligand |
| title_short | Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y2 Receptor Ligand |
| title_sort | synthesis of extended uridine phosphonates derived from an allosteric p2y2 receptor ligand |
| topic | nucleoside phosphonates extended uridine P2Y2 receptor |
| url | http://www.mdpi.com/1420-3049/19/4/4313 |
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