Synthesis of N4-Substituted Derivatives of 1-[2-(Phosphonomethoxy)ethyl]cytosine and Its Diisopropyl Ester as a Model Reaction for the Synthesis of N4-Substituted Derivatives of Cidofovir

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Title:Synthesis of N4-Substituted Derivatives of 1-[2-(Phosphonomethoxy)ethyl]cytosine and Its Diisopropyl Ester as a Model Reaction for the Synthesis of N4-Substituted Derivatives of Cidofovir
Creators:
Chalupová, Šárka
Holý, Antonín
Masojídková, Milena
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 12, pp. 2066-2074
Uncontrolled Keywords:HPMPC, Acyclic nucleoside phosphonates, Transamination, Cidofovir, Pyrimidines, Nucleotides, Amines, Antivirals, Cytosine modification

Abstract

We have studied the reaction of 1-[2-(phosphonomethoxy)ethyl]cytosine (<strong>1</strong>) and its diisopropyl ester (<strong>2</strong>) with triethylammonium hydrogensulfite in 60% aqueous methanol. In the presence of some primary or secondary amine salts, at 25-70 °C, this reaction affords transaminated derivatives <strong>4a</strong>-<strong>4e</strong> and <strong>5a</strong>, <strong>5b</strong> as main products accompanied by uracil compounds. However, with certain amines the reaction failed. <p>

Title:Synthesis of N4-Substituted Derivatives of 1-[2-(Phosphonomethoxy)ethyl]cytosine and Its Diisopropyl Ester as a Model Reaction for the Synthesis of N4-Substituted Derivatives of Cidofovir
Creators:
Chalupová, Šárka
Holý, Antonín
Masojídková, Milena
Uncontrolled Keywords:HPMPC, Acyclic nucleoside phosphonates, Transamination, Cidofovir, Pyrimidines, Nucleotides, Amines, Antivirals, Cytosine modification
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:12
Page Range:pp. 2066-2074
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20052066UNSPECIFIED
ID Code:2456
Item Type:Article
Deposited On:06 Feb 2009 17:18
Last Modified:06 Feb 2009 16:18

Citation

Chalupová, Šárka; Holý, Antonín; Masojídková, Milena (2005) Synthesis of N4-Substituted Derivatives of 1-[2-(Phosphonomethoxy)ethyl]cytosine and Its Diisopropyl Ester as a Model Reaction for the Synthesis of N4-Substituted Derivatives of Cidofovir. Collection of Czechoslovak Chemical Communications, 70 (12). pp. 2066-2074. ISSN 0010-0765

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