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Synthesis of new 1-alkyl-, 1-benzyl-, and 1-aryloxyethyl-substituted 4,5-dichloroimidazoles and their antimicrobial, protistocidal, and fungistatic properties

Abstract

Previously unknown 1-alkyl-, 1-benzyl-, and 1-aryloxyethylderivatives of dichloroimidazoles and products of their structural transformation were synthesized from 4,5-dichloroimidazole or 2-methyl-4,5- dichloroimidazole using alkyl, benzyl or aryloxyethyl halides. These N-substituted compounds were shown to have a weak antibacterial activity against some pathogenic gram-positive and gram-negative bacteria (Staphylococcus aureus and Escherichia coli). At the same time, some of the obtained compounds demonstrated a significant protistocidal activity against Colpoda steinii, which can exceed in strength the activity of clinically used veterinary drug Baycox. Moreover, these compounds showed a pronounced fungistatic effect.

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Correspondence to L. N. Divaeva.

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Original Russian Text © A.A. Kovalenko, L.N. Divaeva, A.A. Zubenko, A.S. Morkovnik, Y.G. Drobin, L.N. Fetisov, A.N. Bodryakov, A.I. Dorofeenko, 2016, published in Bioorganicheskaya Khimiya, 2016, Vol. 42, No. 5, pp. 608–616.

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Kovalenko, A.A., Divaeva, L.N., Zubenko, A.A. et al. Synthesis of new 1-alkyl-, 1-benzyl-, and 1-aryloxyethyl-substituted 4,5-dichloroimidazoles and their antimicrobial, protistocidal, and fungistatic properties. Russ J Bioorg Chem 42, 551–559 (2016). https://doi.org/10.1134/S1068162016040129

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  • DOI: https://doi.org/10.1134/S1068162016040129

Keywords

  • 1-alkyl-
  • 1-benzyl-
  • 1-aryloxyethylsubstituted 4,5-dichloroimidazoles
  • synthesis
  • reduction
  • alkylation
  • metallation
  • antimicrobial activity
  • protistocidal activity
  • fungicidal activity