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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.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Andrei M,Bakkebø T,Klaveness J,Taskén K,Undheim K

doi

10.1016/j.ejmech.2011.10.003

subject

Has Abstract

pub_date

2011-12-01 00:00:00

pages

5935-40

issue

12

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(11)00720-3

journal_volume

46

pub_type

杂志文章

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