- Title
- Syntheses, protonation constants and antimicrobial activity of 2-substituted N-alkylimidazole derivatives
- Creator
- Kleyi, Phumelele
- Creator
- Walmsley, Ryan S
- Creator
- Gundhla, Isaac Z
- Creator
- Walmsley, Tara A
- Creator
- Jauka, Tembisa I
- Creator
- Dames, Joanna F
- Creator
- Walker, Roderick B
- Creator
- Torto, Nelson
- Creator
- Tshentu, Zenixole R
- Subject
- To be catalogued
- Date Issued
- 2012
- 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
- Format
- online resource
- Format
- application/pdf
- Format
- 1 online resource (8 pages)
- Format
- Publisher
- African Journals Online
- Language
- English
- Relation
- South African Journal of Chemistry
- Relation
- 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
- Relation
- 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
- Hits: 3142
- Visitors: 3416
- Downloads: 320
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 Download | SOURCE1 | Syntheses, protonation constants and antimicrobial activity of 2-substituted N-alkylimidazole derivatives.pdf | 271 KB | Adobe Acrobat PDF | View Details Download |