High-pressure synthesis of enantiomerically pure C-6 substituted pyrazol.
The synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines has been performed by aromatic nucleophilic substitution of 4-amino-6-chloro-1-phenylpyrazolo[3,4-rd]pyrimidine under conditions of high pressure at ambient temperature. Conventional synthetic conditions (reflux at atmospheric pressure) were unsuccessful. The S enantiomer 11 displayed higher affinity and selectivity for the adenosine A1 receptor than the R enantiomer 12.
Poulsen
S A
SA
AstraZeneca R&D Griffith University, Brisbane, Australia.
Young
D J
DJ
Quinn
R J
RJ
D000818:Animals; D001479:Basal Ganglia / Q000166:cytology / Q000648:ultrastructure; D001667:Binding, Competitive; D002462:Cell Membrane / Q000737:chemistry; D011312:Pressure; D011485:Protein Binding; D058906:Purinergic P1 Receptor Agonists; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000378:metabolism*; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000378:metabolism*; D051381:Rats; D018047:Receptors, Purinergic P1 / Q000378:metabolism; D013237:Stereoisomerism
D058906:Purinergic P1 Receptor Agonists; D011720:Pyrazoles; D011743:Pyrimidines; D018047:Receptors, Purinergic P1; C014175:pyrazolo(3,4-d)pyrimidine