Abstract
A number of new 2,6-disubstituted-1-deazanebularine analogues as well as two structurally related pyrazole-fused tricyclic nucleosides were prepared. Their synthesis was carried out by the conversion of 6-amino-2-picoline to a suitable 1-deazapurine, followed by a Vorbrüggen type glycosylation and subsequent elaboration of the condensed pyrazole ring. The synthesized nebularine analogues proved to be weak adenosine deaminase inhibitors.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Adenosine Deaminase / chemistry*
-
Adenosine Deaminase / metabolism
-
Adenosine Deaminase Inhibitors / chemical synthesis*
-
Adenosine Deaminase Inhibitors / chemistry
-
Adenosine Deaminase Inhibitors / metabolism
-
Animals
-
Cattle
-
Glycosylation
-
Magnetic Resonance Spectroscopy
-
Protein Binding
-
Purine Nucleosides / chemical synthesis
-
Purine Nucleosides / chemistry*
-
Purine Nucleosides / metabolism
-
Pyrazoles / chemistry
-
Ribonucleosides / chemical synthesis
-
Ribonucleosides / chemistry*
-
Ribonucleosides / metabolism
Substances
-
Adenosine Deaminase Inhibitors
-
Purine Nucleosides
-
Pyrazoles
-
Ribonucleosides
-
pyrazole
-
nebularine
-
Adenosine Deaminase