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Molecules 2014, 19(4), 4313-4325;

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

Laboratory for Medicinal Chemistry, Ghent University, Harelbekestraat 72, B-9000 Ghent, Belgium
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. View Full-Text
Keywords: nucleoside phosphonates; extended uridine; P2Y2 receptor nucleoside phosphonates; extended uridine; P2Y2 receptor

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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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