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Synthesis of sydnonimine derivatives as potential trypanocidal agents
Author(s) -
Soulère Laurent,
Hoffmanna Pascal,
Bringaud Frédéric
Publication year - 2003
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570400533
Subject(s) - chemistry , peroxynitrite , superoxide , purine , nitrone , nitric oxide , stereochemistry , medicinal chemistry , organic chemistry , cycloaddition , catalysis , enzyme
N ‐( p ‐Nitrophenoxy)carbonyl‐3‐morpholino‐sydnonimine (NCMS) has been prepared from 3‐morpholinosydnonimine hydrochloride. Using the Griess assay and the superoxide‐mediated reduction of ferricytochrome c, the nitric oxide (NO•) and superoxide anion (O 2 • ‐ ) ‐ releasing properties in phosphate buffer pH 7.4 of this novel peroxynitrite donor was studied and compared with the known 3‐morpholino‐sydnonimine (SIN‐1). From compound NCMS, a series of N‐substituted sydnonimine derivatives were easily prepared that contain purine or melaminophenyl groups which specify a recognition by a trypanosomal purine transporter. The ability of these new sydnonimines to inhibit the uptake of [2 3 H]adenosine on Trypanosoma equiperdum was studied.