Format

Send to

Choose Destination
J Med Chem. 2000 Nov 30;43(24):4694-700.

Adenosine deaminase inhibitors: synthesis and biological evaluation of unsaturated, aromatic, and oxo derivatives of (+)-erythro-9-(2'S-hydroxy-3'R-nonyl)adenine [(+)-EHNA].

Author information

1
Department of Chemistry, University of Rhode Island, Kingston, Rhode Island 02881-0809, USA.

Abstract

The synthesis and biological evaluation of three classes of chain-modified derivatives of (+)-EHNA are described. Among the 5', 6'-unsaturated derivatives, the Z-isomer was the most potent inhibitor of adenosine deaminase (ADA) but 3-fold less active than (+)-EHNA. Several 9-aralkyladenines (ARADs) have been prepared, and their inhibitory activity was determined. A minimum of two carbon atoms separating the aromatic ring from the adenine-bearing carbon (C-3') was found to be essential for ADA activity equal to or slightly greater than that of (+)-EHNA. Finally, replacement of the C-5' carbon with an oxygen resulted in reduced potency.

PMID:
11101360
DOI:
10.1021/jm0002533
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for American Chemical Society
Loading ...
Support Center