oa South African Journal of Chemistry - Syntheses, protonation constants and antimicrobial activity of 2-substituted -alkylimidazole derivatives : research article

Volume 65, Issue 1
  • ISSN : 0379-4350



A series of -alkylimidazole-2-carboxylic acid, -alkylimidazole-2-carboxaldehyde and -alkylimidazole-2-methanol derivatives [alkyl = benzyl, methyl, ethyl, propyl, butyl, heptyl, octyl and decyl] have been synthesized and the protonation constants determined. The antimicrobial properties of the compounds were tested against Gram-negative (), Gram-positive ( & subsp. ) bacterial strains and yeast (). Both the disk diffusion and broth microdilution methods for testing the antimicrobial activity showed that -alkylation of imidazole with longer alkyl chains and the substitution with low p group at 2-position resulted in enhanced antimicrobial activity. Particularly, the -alkylimidazole-2-carboxylic acids exhibited the best antimicrobial activity due to the low p of the carboxylic acid moiety. Generally, all the -alkylimidazole derivatives were most active against the Gram-positive bacteria [ (MIC = 5-160 g mL-1) and subsp. (5-20 g mL-1)], with the latter more susceptible. All the compounds showed poor antimicrobial activity against both Gram-negative (, MIC = 0.15 to >2500 g mL-1) bacteria and all the compounds were inactive against the yeast ().

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