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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Studies on anticoccidial agents. 11. Synthesis and anticoccidial activity of nitropyridinecarboxamides and derivatives.

Of the nine nitropyridinecarboxamides, which are isomers of 5-nitronicotinamide, a potent anticoccidial agent, 2-nitropyridine-3, -4, -5-, or 6-carboxamides and 3-nitropyridine-4- or 6-carboxamides were prepared from the corresponding acids via the esters of the acid chlorides. 3-Nitropyridine-2-carboxamide was obtained from 2-methyl-3-nitropyridine by oxidation with SeO2, oximation, dehydration with Ac2O, and hydrolysis with H2SO4. 4-Nitropyridine-2-carboxamide was prepared from 2-cyano-4-nitropyridine by hydrolysis, and the 3-carboxamide analogue was obtained from 4-amino-3-cyanopyridine by oxidation with H2O2 and fuming H2SO4. Of these compounds 2-nitro- and 3-nitro- but not 4-nitropyridinecarboxamides were found to be active against Eimeria tenella. N-Substituted analogues of 2-nitro- and 3-nitropyridine carboxamides were also prepared in a conventional manner and optimal anticoccidial activity was attained with 2-nitroisonicotinamide and its N-alkanoyl, N-aromatic, and N-heterocyclic acyl derivatives.[1]


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