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SYNTHESIS AND HALOGENATION OF 2-METHYLIMIDAZO[1,2-a]PYRIDINE. ANTIMICROBIAL ACTIVITY OF 3-BROMO-2-METHYL-1Н-IMIDAZO[1,2-a]PYRIDINIUM BROMIDE

Елена В. Калита, Дмитрий Г. Ким, Елизавета М. Крынина, Владимир В. Шарутин, Нина М. Шлепотина, Олег Л. Колесников, Юлия С. Шишкова, Маргарита В. Пешикова
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Abstract


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 μg/ml.

Keywords


2-aminopyridine; 3-halo-2-methyl-1Н-imidazo[1,2-a]pyridinium trihalides and halides; 2-methylimidazo[1,2-a]pyridine; alkylation; antimicrobial activity; halogenation.

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