New (1-deaza)purine derivatives via efficient C-2 nitration of the (1-deaza)purine ring.

Nitration of substituted (1-deaza)purines using a mixture of tetrabutylammonium nitrate (TBAN) and trifluoracetic acid anhydride (TFAA) was applied to prepare nitrosubstituted (1-deaza)purines at low temperature. The nitro group influences the system twofold: 1) it activates other substituents towards nucleophilic aromatic substitution and 2) it can be substituted itself leading to a variety of di-substituted (1-deaza)purines, also via solid phase syntheses. Several of the molecules obtained were studied for their antiprotozoal activity and for interactions with the different human adenosine receptors.