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

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.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Pragnacharyulu PV,Varkhedkar V,Curtis MA,Chang IF,Abushanab E

doi

10.1021/jm0002533

keywords:

subject

Has Abstract

pub_date

2000-11-30 00:00:00

pages

4694-700

issue

24

eissn

0022-2623

issn

1520-4804

pii

jm0002533

journal_volume

43

pub_type

杂志文章

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