Collect. Czech. Chem. Commun.
2005, 70, 2066-2074
https://doi.org/10.1135/cccc20052066
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
Šárka Chalupová*, Antonín Holý and Milena Masojídková
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
Abstract
We have studied the reaction of 1-[2-(phosphonomethoxy)ethyl]cytosine (1) and its diisopropyl ester (2) 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 4a-4e and 5a, 5b as main products accompanied by uracil compounds. However, with certain amines the reaction failed.
Keywords: Cytosine modification; Antivirals; Cidofovir; HPMPC; Acyclic nucleoside phosphonates; Nucleotides; Pyrimidines; Transamination; Amines.
References: 10 live references.
