title: Stereoselective synthesis of (RP)-8-substituted-N⁶-acylated and N⁶-alkylated adenosine-3',5'-cyclic phosphorothioic acids as cAMP antagonists.
abstract: N(6)-Monoalkylated, N(6)-dialkylated and N(6)-acylated (R(P))-adenosine 3',5'-cyclic phosphorothioic acids have been prepared by stereoselective syntheses from cAMP for a study of protein kinase A antagonist activity. The antagonist activity of the parent primary 6-amino cAMP derivative was reduced after N-monoalkylation. No significant activity was detected in the N,N-dialkylated derivative. Mono N-acylation had little effect on the activity. Hydrogen bonding involving the 6-amino group in cAMPS seems necessary for activity.
authors: Lauras, Gaustadalléen 21, N-0349 Oslo, Norway.
authors: Mioara
authors: M
authors: Andrei
authors: Tina
authors: T
authors: Bakkebø
authors: Jo
authors: J
authors: Klaveness
authors: Kjetil
authors: K
authors: Taskén
authors: Kjell
authors: K
authors: Undheim
mesh_terms: D000215:Acylation; D000478:Alkylation; D000242:Cyclic AMP / Q000031:analogs & derivatives* / Q000037:antagonists & inhibitors* / Q000378:metabolism; D006860:Hydrogen Bonding; D007700:Kinetics; D010710:Phosphates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D010710:Phosphates; D000242:Cyclic AMP; C035638:thiophosphoric acid