Study of chemical stability of antivirally active 5-azacytosine acyclic nucleoside phosphonates using NMR spectroscopy.
Hydrolytic decomposition of four 5-azacytosine acyclic nucleoside phosphonates was studied. Products of the decomposition are carbamoylguanidine derivatives. Stability and decomposition products of HPMP-5-azaC (a 5-azacytosine derivative with strong antiviral activity) differ from the other derivatives. The reaction pathway of HPMP-5-azaC involves a formyl derivative formed by intramolecular transformylation reaction.
Gilead Sciences & IOCB Research Centre, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, CZ-166 10 Prague 6, Czech Republic. dracinsky@uochb.cas.cz
Martin
M
Dracínský
Marcela
M
Krecmerová
Antonín
A
Holý
D000998:Antiviral Agents / Q000737:chemistry*; D003596:Cytosine / Q000031:analogs & derivatives* / Q000737:chemistry; D004355:Drug Stability; D006146:Guanidines; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*
D000998:Antiviral Agents; D006146:Guanidines; D009705:Nucleosides; D063065:Organophosphonates; C039854:5-azacytosine; D003596:Cytosine