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Paper | Regular issue | Vol 83, No. 4, 2011, pp.797-813
Published online, 1st March, 2011
DOI: 10.3987/COM-11-12137
Synthesis of O2- and N3-(2-Phosphonomethoxy)ethyl Derivatives of 6-Phenyl- and 6-Pyridinyl-5-azacytosine

Miroslav Otmar,* Martin Dracinsky, Marcela Krecmerova, Jan Balzarini, Graciela Andrei, and Robert Snoeck

*Gilead Sciences and IOCB Research Centre, Centre for New Antivirals and Antineoplastics, Institute of Organic Chemistry and Biochemistry, Flemingovo nam. 2, 16610 Prague 6, Czech Republic


A series of hydrolytically stable O2- and N3-(2-phosphonomethoxy)- ethyl (PME) derivatives of 6-phenyl, pyridin-2, -3 and -4-yl-5-azacytosines was prepared by their alkylation with diisopropyl (2-chloroethoxy)methylphosphonate followed by the deprotection. No antitumor or antiviral activity was found except for 6-(pyridin-4-yl)-1,3,5-triazine-2,4-diamine (13d) which exhibited slight activity against feline herpesvirus in CrFK cell cultures with IC50 = 6.7 µg/mL.