Abstract:
:5-Nitronicotinamide (1) was prepared from 5-bromonicotinoyl chloride by treatment with ammonia and then oxidation with fuming H2SO4 and 30% H202. 2-Cholor-, 2-alkoxy-2-benzyloxy,2-phenoxy-,2-alkylamino-, and 2-benzylamino-5-nitronicatinamides were also prepared via 2-chloro-3-cyano-5-nitropyridine. 2-Methyl-5-nitronicotinamide (2) was obtained from ethyl 2-methyl-5-nitronicotinate by treatment with ammonia; the 4-methyl analogue 3 was from 3-cyano-2,6-dihydroxy-4 methylpyridine by nitration, chlorination, and dechlorination, and the 6-methyl analogue 4 was prepared by transforming 2-chloro-3-cyano-6-methyl-5-nitropyridine to the corresponding amide, followed by dechlorination. Of these compounds, the 5-nitronicotinamide, the 2-methyl and 4-methyl but not the 6-methyl, analogue showed significant anticoccidial activity against eimeria tenella. N-Substituted analogues of 5-nitronicotinamide and 2-methyl-5-nitronicotinamide were prepared in a conventional manner and optimal anticoccidial activity was attained with their lower N-alkyl analogues, N-alkanoyl and -alkenoyl analogues, and N-aromatic acyl analogues together with these parent compounds.
journal_name
J Med Chemjournal_title
Journal of medicinal chemistryauthors
Morisawa Y,Kataoka M,Kitano N,Matsuzawa Tdoi
10.1021/jm00211a027keywords:
subject
Has Abstractpub_date
1977-01-01 00:00:00pages
129-33issue
1eissn
0022-2623issn
1520-4804journal_volume
20pub_type
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