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New drugs are urgently required for treatment of human African trypanosomiasis and Chagas´ disease. One compound with promise is megazol, a nitro heterocyclic compound that forms a nitro radical anion upon reduction. Megazol (2-amino-5-(1-methyl-5-nitro-2-imidazolyl)-1,3,4-thiadiazol) and related nitroimidazole compounds are being tested as antichagasic drugs. Little is known on the mode of action of megazol. However, there is evidence that 1-electron reduction of megazol to the corresponding nitro radical anion is a key step in the reaction mechanism.
It was observed that the obtaining of megazol can be made by different paths synthetic modifying procedures and reagents involved in the chemistry of heterocyclic particularly imidazoles. We evaluated experimental conditions, partial and overall income, as well as the characteristics of reagents involved in the processes indicated in one of the routes. Megazol was prepd. from 1-methylimidazole by cyanation, cyclization with thiosemicarbazide, nitration with concomitant acetylating of the amino group, and deacetylation.
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Author(s): Arantes F Jnior HL Moreto S Albuquerque CND
Synthesis, Heterocyclic, Imidazole, Megazol