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Identification of 4-Substituted 1,2,3-Triazoles as Novel Oxazolidinone Antibacterial Agents with Reduced Activity against Monoamine Oxidase A
Open accessAbstract
Oxazolidinones represent a new and promising class of antibacterial agents. Current research in this area is mainly concentrated on improving the safety profile and the antibacterial spectrum. Many oxazolidinones, including linezolid (marketed as Zyvox), are inhibitors of monoamine oxidase A (MAO-A), which presents an undesired side effect. Recently, it was found that the 1,2,3-triazole is a good replacement for the conventional acetamide functionality found in oxazolidinones. We now disclose the finding that 1,2,3-triazoles bearing a substituent like methyl, small substituted methyl, bromo, or a linear (sp-hybridized) group at the 4 position (compounds such as 5, 16, 19, and 21) are good antibacterials with reduced or no activity, within the detection limit of the assay, against MAO-A. The results are especially promising for the development of oxazolidinones with an improved safety profile. The MAO-A SAR can be rationalized on the basis of docking studies to a MAO-A/MAO-B homology model.
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Cites
Tornøe, C. W., Christensen, C., & Meldal, M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo011148j · Cited by 8,696
Cited by
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Bock, V. D., Hiemstra, H., & van Maarseveen, J. H. (2006) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200500483 · Cited by 1,452
Metadata
- Authors
- Reck, F., Zhou, F., Girardot, M., Kern, G., Eyermann, C. J., Hales, N. J., Ramsay, R. R., & Gravestock, M. B.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-01-01
- Volume
- 48
- Issue
- 2
- Pages
- 499-506
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2017662055
- Cited by
- 332
- References
- 1
- FWCI
- 6.75
- Type
- journal article
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: Identification of 4-Substituted 1,2,3-Triazoles as Novel Oxazolidinone Antibacterial Agents with Reduced Activity against Monoamine Oxidase A. https://app.cochat.ai/papers/10.1021/jm0400810
- The paper
- Reck, F., Zhou, F., Girardot, M., Kern, G., Eyermann, C. J., Hales, N. J., Ramsay, R. R., & Gravestock, M. B. (2005). Identification of 4-Substituted 1,2,3-Triazoles as Novel Oxazolidinone Antibacterial Agents with Reduced Activity against Monoamine Oxidase A. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm0400810
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