Simple Transformation of Thymine 1-[3-Hydroxy-2-(phosphonomethoxy)propyl] Derivatives to Their 1-[3-Fluoro-2-(phosphonomethoxy)propyl] Counterparts

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Title:Simple Transformation of Thymine 1-[3-Hydroxy-2-(phosphonomethoxy)propyl] Derivatives to Their 1-[3-Fluoro-2-(phosphonomethoxy)propyl] Counterparts
Creators:
Pomeisl, Karel
Pohl, Radek
Holý, Antonín
Votruba, Ivan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 9, pp. 1465-1481
Uncontrolled Keywords:Acyclic nucleoside phosphonates, Pyrimidines, Deoxyfluorinations, Thymidine phosphorylase, Acyclic nucleotide analogues, Thymine, Antivirals

Abstract

A novel method of transformation of HOCH<sub>2</sub> group to FCH<sub>2</sub> was successfully applied to the preparation of fluorine-containing pyrimidine acyclic nucleoside phosphonates (FPMP compounds) such as (<i>S</i>)- and (<i>R</i>)-1-[3-fluoro-2-(phosphonomethoxy)propyl]thymine (<strong>7a</strong>, <strong>7b</strong>) (FPMPT). The key displacement of hydroxy group with fluorine in 1-{2-[(diisopropoxyphosphoryl)- methoxy]-3-hydroxypropyl}-4-methoxy-5-methylpyrimidin-2(1<i>H</i>)-one (<strong>5a</strong>, <strong>5b</strong>) was performed using perfluorobutane-1-sulfonyl fluoride in the presence of DBU. Novel pyrimidine acyclic nucleoside phosphonates were investigated as inhibitors of thymidine phosphorylase. <p>

Title:Simple Transformation of Thymine 1-[3-Hydroxy-2-(phosphonomethoxy)propyl] Derivatives to Their 1-[3-Fluoro-2-(phosphonomethoxy)propyl] Counterparts
Creators:
Pomeisl, Karel
Pohl, Radek
Holý, Antonín
Votruba, Ivan
Uncontrolled Keywords:Acyclic nucleoside phosphonates, Pyrimidines, Deoxyfluorinations, Thymidine phosphorylase, Acyclic nucleotide analogues, Thymine, Antivirals
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:70
Number:9
Page Range:pp. 1465-1481
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20051465UNSPECIFIED
ID Code:2423
Item Type:Article
Deposited On:06 Feb 2009 17:18
Last Modified:06 Feb 2009 16:18

Citation

Pomeisl, Karel; Pohl, Radek; Holý, Antonín; Votruba, Ivan (2005) Simple Transformation of Thymine 1-[3-Hydroxy-2-(phosphonomethoxy)propyl] Derivatives to Their 1-[3-Fluoro-2-(phosphonomethoxy)propyl] Counterparts. Collection of Czechoslovak Chemical Communications, 70 (9). pp. 1465-1481. ISSN 0010-0765

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