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Molecules 2014, 19(4), 4313-4325; doi:10.3390/molecules19044313

Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y2 Receptor Ligand

1 Laboratory for Medicinal Chemistry, Ghent University, Harelbekestraat 72, B-9000 Ghent, Belgium 2 Department of Pharmacology, University of North Carolina, School of Medicine, Chapel Hill, NC 27599-7365, USA
* Author to whom correspondence should be addressed.
Received: 24 February 2014 / Revised: 28 March 2014 / Accepted: 31 March 2014 / Published: 4 April 2014
(This article belongs to the Section Medicinal Chemistry)
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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.
Keywords: nucleoside phosphonates; extended uridine; P2Y2 receptor nucleoside phosphonates; extended uridine; P2Y2 receptor
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Song, L.; Risseeuw, M.D.P.; Karalic, I.; Barrett, M.O.; Brown, K.A.; Harden, T.K.; Van Calenbergh, S. Synthesis of Extended Uridine Phosphonates Derived from an Allosteric P2Y2 Receptor Ligand. Molecules 2014, 19, 4313-4325.

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