Format

Send to

Choose Destination
J Org Chem. 2011 Apr 15;76(8):2899-903. doi: 10.1021/jo102579g. Epub 2011 Mar 23.

Synthesis of fluorinated purine and 1-deazapurine glycosides as potential inhibitors of adenosine deaminase.

Author information

1
Institut für Chemie der Universität Rostock, Albert-Einstein-Strasse 3a, D-18059 Rostock, Germany. viktor.iaroshenko@uni-rostock.de

Abstract

The synthesis of 2- and 6-trifluoromethylated purines and 1-deazapurines was performed by formal [3 + 3]-cyclization reactions of 5-aminoimidazoles with a set of trifluoromethyl-substituted 1,3-CCC- and 1,3-CNC-dielectrophiles. The corresponding fluorinated nucleosides were synthesized by glycosylation of 9-unsubstituted purines and 1-deazapurines with peracetylated β-ribose, β-glucose, and rhamnose and subsequent deprotection. These scaffolds can be considered as potential inhibitors of adenosine deaminase (ADA) and inosine monophosphate dehydrogenase (IMPDH) enzymes.

PMID:
21395333
DOI:
10.1021/jo102579g
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for American Chemical Society
Loading ...
Support Center