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Keywords:

acyclic nucleoside phosphonate, pmea, ethyne nucleoside, antiviral agents, thymidine phosphorylase, dihydro-2h-pyranyl nucleosides, derivatives, inhibitors, infections, analogs, bases, hiv, Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, Acyclic nucleoside phosphonate, PMEA, Ethyne nucleoside, Antiviral agents, DERIVATIVES, INHIBITORS, ANALOGS, HIV, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3101 Biochemistry and cell biology, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

A series of 2' functionalized acyclic nucleoside phosphonate derivatives of 1-[3'-(phosphonomethoxy)propyl]uracil (1-4) have been synthesized together with the 1' and 2'-ethynyl derivatives of 9/1-[2'-(phosphonomethoxy)ethyl]adenine/thymine (5-7). Key intermediates leading to the latter series are (+/-)-[2-{diethyl(phosphonomethoxy)}-1-hydroxy]-but-3-yne (25) and (+/-)-diisopropyl{[2-hydroxy-4-(trimethylsilyl)but-3-yn-1-yl]oxy}methylphosphonate (30). Compounds 25 and 30 are easily obtained starting from (+/-)-solketal. (C) 2011 Elsevier Ltd. All rights reserved.