Synthesis and halogenation of 2-methylimidazo[1,2-a]pyridine. Antimicrobial activity of 3-bromo-2-methyl-1Ð-imidazo[1,2-a]pyridinium bromide

Imidazo[1,2-a]pyridine derivatives have been shown to possess a broad range of biological activity. 2-Amino-1-propargylpyridinium and 2-amino-1-(2-bromoallyl)pyridinium bromides, the structures of which were established on the basis of X-ray structural analysis, reacted with sodium methoxide, leadin...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2022-05, Vol.58 (4-5), p.227
Main Authors: Kalita, Elena V, Kim, Dmitry G, Krynina, Elizaveta M, Sharutin, Vladimir V, Shlepotina, Nina M, Kolesnikov, Oleg L, Shishkova, Yulia S
Format: Article
Language:English
Subjects:
Medical colleges
Methicillin
Pyridine
Staphylococcus aureus infections
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Summary:Imidazo[1,2-a]pyridine derivatives have been shown to possess a broad range of biological activity. 2-Amino-1-propargylpyridinium and 2-amino-1-(2-bromoallyl)pyridinium bromides, the structures of which were established on the basis of X-ray structural analysis, reacted with sodium methoxide, leading to the formation of 2-methylimidazo[1,2-a]pyridine. 2-Methylimidazo[1,2-a]pyridine further reacted with bromine and iodine, providing 3-halo-2-methyl-1H-imidazo[1,2-a]pyridinium trihalides, the structure of which was confirmed by X-ray structural analysis. 3-Halo-2-methyl-1H-imidazo[1,2-a]pyridinium halides were obtained from the respective trihalides. 3-Bromo- 2-methyl-1H-imidazo[1,2-a]pyridinium bromide showed antimicrobial properties against Staphylococcus aureus at the concentrations of 2700 and 675 [mu]g/ml.
ISSN:0009-3122
DOI:10.1007/s10593-022-03076-9