Collect. Czech. Chem. Commun. 2006, 71, 1303-1319

Synthesis and Properties of 2-Guanidinopurines

Michal Česnek*, Milena Masojídková, Antonín Holý, Veronika Šolínová, Dušan Koval and Václav Kašička

Gilead Sciences & IOCB Research Center; Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic


2-Guanidinopurines were prepared as derivatives of 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]-9H-purine (PMEDAP) (1), which shows an important antiviral activity. It completes earlier described synthesis of 6-guanidinopurine derivatives. The title compounds were obtained by the reaction of the corresponding 2-chloropurines with guanidine. 2- And 6-guanidinopurines were used as model compounds for determination of dissociation constants (pKa) of their ionogenic groups by capillary zone electrophoresis. The pKa values of ionogenic groups of the above compounds were compared with those of the corresponding aminopurines. The pKa of guanidino group at the purine moiety varies from 7.77 to 10.32. There is no protonation of N1-position in contrast to aminopurines. None of these compounds showed any antiviral activity.

Keywords: Purines; Nucleosides; Guanidines; Basicity; Dissociation constants; PMEDAP analogues; Acyclic nucleoside phosphonates; Electrophoresis.

References: 28 live references.