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Synthesis of sydnonimine derivatives as potential trypanocidal agents

✍ Scribed by Laurent Soulère; Dr. Pascal Hoffmanna; Frédéric Bringaud

Publisher
Journal of Heterocyclic Chemistry
Year
2003
Tongue
English
Weight
69 KB
Volume
40
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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.

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## Abstract The synthesis of new indazol‐4,7‐dione derivatives __via__ 1,3‐dipolar cycloaddition of diazomethane with 2,3‐dimethyl‐1,4‐benzoquinone (**2**) and 1,4‐naphthoquinone (**7**) followed by __N__‐alkylation of the pyrazol nitrogen atom of the corresponding quinones (**3**) and (**8**) with