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.
Wanner
M J
MJ
Bioorganic Chemistry, Institute of Molecular Chemistry, University of Amsterdam, Amsterdam, The Netherlands.
Rodenko
B
B
Koch
M
M
Koomen
G J
GJ
D000089:Acetic Anhydrides; D000981:Antiprotozoal Agents / Q000494:pharmacology; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D003606:Dacarbazine / Q000031:analogs & derivatives* / Q000737:chemistry; D004583:Electrons; D005463:Fluoroacetates; D006801:Humans; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry*; D011687:Purines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D018047:Receptors, Purinergic P1 / Q000737:chemistry; D000077204:Temozolomide; D013696:Temperature; D014269:Trifluoroacetic Acid / Q000737:chemistry*
D000089:Acetic Anhydrides; D000981:Antiprotozoal Agents; D005463:Fluoroacetates; D011687:Purines; D018047:Receptors, Purinergic P1; C064191:1H-imidazo(4,5-b)pyridine; C017958:trifluoroacetic anhydride; D003606:Dacarbazine; D014269:Trifluoroacetic Acid; D009584:Nitrogen; D000077204:Temozolomide