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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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. South Ural State University (National Research University), 76 Lenina Ave, Chelyabinsk, 454080, Russia

    Elena V. Kalita, Dmitry G. Kim, Elizaveta M. Krynina & Vladimir V. Sharutin

  2. Moscow Institute of Physics and Technology (National Research University), 9 Institutskiy Per., Dolgoprudny, Moscow Region, 141701, Russia

    Elena V. Kalita

  3. South Ural State Medical University, Ministry of Health of the Russian Federation, 64 Vorovskogo St, Chelyabinsk, 454092, Russia

    Nina M. Shlepotina, Oleg L. Kolesnikov, Yulia S. Shishkova & Margarita V. Peshikova

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  1. Elena V. Kalita
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  2. Dmitry G. Kim
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  3. Elizaveta M. Krynina
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  4. Vladimir V. Sharutin
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  5. Nina M. Shlepotina
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  6. Oleg L. Kolesnikov
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  7. Yulia S. Shishkova
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  8. Margarita V. Peshikova
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Correspondence to Elena V. Kalita.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(4/5), 227–234

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Kalita, E.V., Kim, D.G., Krynina, E.M. et al. Synthesis and halogenation of 2-methylimidazo[1,2-a]pyridine. Antimicrobial activity of 3-bromo-2-methyl-1Н-imidazo[1,2-a]pyridinium bromide. Chem Heterocycl Comp 58, 227–234 (2022). https://doi.org/10.1007/s10593-022-03076-9

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  • DOI: https://doi.org/10.1007/s10593-022-03076-9

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