- Title
- Syntheses, protonation constants and antimicrobial activity of 2-substituted N-alkylimidazole derivatives
- Creator
- Kleyi, Phumelele, Walmsley, Ryan S, Gundhla, Isaac Z, Walmsley, Tara A, Jauka, Tembisa I, Dames, Joanna F, Walker, Roderick B, Torto, Nelson, Tshentu, Zenixole R
- Subject
- To be catalogued
- Date
- 2012
- Type
- text
- Type
- article
- Identifier
- http://hdl.handle.net/10962/184066
- Identifier
- vital:44165
- Identifier
- xlink:href="https://www.ajol.info/index.php/sajc/article/view/123858"
- Description
- A series of N-alkylimidazole-2-carboxylic acid, N-alkylimidazole-2-carboxaldehyde and N-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 (Escherichi coli), Gram-positive (Staphylococcus aureus and Bacillus subtilis subsp. spizizenii) bacterial strains and yeast (C. albicans). Both the disk diffusion and broth microdilution methods for testing the antimicrobial activity showed that N-alkylation of imidazole with longer alkyl chains and the substitution with low pKa group at 2-position resulted in enhanced antimicrobial activity. Particularly, the N-alkylimidazole-2-carboxylic acids exhibited the best antimicrobial activity due to the low pKa of the carboxylic acid moiety. Generally, all the N-alkylimidazole derivatives were most active against the Gram-positive bacteria [S. aureus (MIC = 5–160 µg mL–1) and B. subtilis subsp. spizizenii (5–20 µg mL–1)], with the latter more susceptible. All the compounds showed poor antimicrobial activity against both Gram-negative (E. coli, MIC = 0.15 to >2500 µg mL–1) bacteria and all the compounds were inactive against the yeast (Candida albicans).
- Format
- computer, online resource, application/pdf, 1 online resource (8 pages), pdf
- Publisher
- African Journals Online
- Language
- English
- Relation
- South African Journal of Chemistry, Kleyi, P., Walmsley, R.S., Gundhla, I.Z., Walmsley, T.A., Jauka, T.I., Dames, J., Walker, R.B., Torto, N. and Tshentu, Z.R., 2012. Syntheses, protonation constants and antimicrobial activity of 2-substituted N-alkylimidazole derivatives. South African Journal of Chemistry, 65, pp.231-238, South African Journal of Chemistry volume 65 p. 231 2012 0379-4350
- Rights
- Publisher
- Rights
- Use of this resource is governed by the terms and conditions of the Creative Commons CC BY 4.0 License (Attribution 4.0 International) https://creativecommons.org/licenses/by/4.0/
- Rights
- Open Access
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Collections
Tshentu, Zenixole Richman (Dr)
Walker, Roderick Bryan (Prof)
Torto, Nelson (Prof)
Dames, Joanna Felicity (Prof)
RU Department of Pharmacy
SDG 03. Good Health and Well-Being
| Thumbnail | File | Description | Size | Format | |||
|---|---|---|---|---|---|---|---|
| View Details | SOURCE1 | Syntheses, protonation constants and antimicrobial activity of 2-substituted N-alkylimidazole derivatives.pdf | 271 KB | Adobe Acrobat PDF | View Details |