Synthesis of potential purinoceptor antagonists: application of P1-tBU phosphazene base for alkylation of adenine in solution and on solid phase.
Alkylation of adenine in solution and on solid phase was accelerated by phosphazene base P1-tBu compared to mineral bases. The reactions in solution afforded regioselectively the appropriate N9-alkylated adenines with high preparative yields while the reaction with polystyrene resin-bound N-bromoacetylated peptides gave three regioisomers (alkylated at the N9, N7, and N3 position of adenine) in a 4:2:1 molar ratio. Ten novel nonphosphate nucleotide analogues were tested in an ADP-induced platelet aggregation assay.
Institute of Organic and Bioorganic Chemistry, University of Tartu, Tartu, Estonia.
Erki
E
Enkvist
Gerda
G
Raidaru
Asko
A
Uri
Roshni
R
Patel
Catherine
C
Redick
José L
JL
Boyer
Juhan
J
Subbi
Indrek
I
Tammiste
D000225:Adenine / Q000031:analogs & derivatives / Q000737:chemistry* / Q000494:pharmacology*; D000478:Alkylation; D001388:Aziridines / Q000737:chemistry*; D006801:Humans; D010753:Phosphoranes / Q000737:chemistry* / Q000494:pharmacology; D010975:Platelet Aggregation Inhibitors / Q000494:pharmacology; D011137:Polystyrenes / Q000737:chemistry*; D058914:Purinergic Antagonists; D012996:Solutions / Q000737:chemistry*; D013237:Stereoisomerism; D013997:Time Factors
D001388:Aziridines; C510992:P1-tBU phosphazene; D010753:Phosphoranes; D010975:Platelet Aggregation Inhibitors; D011137:Polystyrenes; D058914:Purinergic Antagonists; D012996:Solutions; C008880:phosphazine; D000225:Adenine