Easy Access to Evans’ Oxazolidinones. Stereoselective Synthesis and Antibacterial Activity of a New 2-Oxazolidinone Derivative
Abstract
:1. Introduction
1.1. Evans’ Oxazolidinones
1.2. Oxazolidinone Derivatives
2. Results and Discussion
2.1. Preparation of Evans’ Oxazolidinones 1 and 2
2.2. Preparation of 2-Oxazolidinone Derivative 5
2.3. Antibacterial Activity
S. aureus | Compound 5 | Compound 14 | Ciclopirox Olamine | DMSO |
---|---|---|---|---|
680 | 19.0 ± 0.58 | 2.0 ± 0.48 | 17.0 ± 0.58 | 0.00 |
2221 | 18.0 ± 0.60 | NA | 18.0 ± 0.60 | 0.00 |
4006 | 21.0 ± 0.33 | 2.0 ± 0.58 | 17.0 ± 0.58 | 0.00 |
4075 | 15.0 ± 0.67 | NA | 17.0 ± 0.58 | 0.00 |
4127 | 16.0 ± 0.58 | 2.0 ± 0.50 | 17.0 ± 0.50 | 0.00 |
MIC (μg mL−1) | |
---|---|
Compound 5 | 0.03 |
Ciclopirox olamine | 0.05 |
3. Experimental
3.1. General Procedures
3.2. Synthesis
3.2.1. General Procedure for the Synthesis of Evans’ Oxazolidinones 1 and 2
3.2.2. (−)-(3S,4S)-4-Tert-butoxycarbonylamino-3-hydroxy-2-methylene-5-phenylpentanoic Acid Methyl Ester (6) [11]
3.2.3. (+)-(4S,5S)-4-Benzyl-5-(1-Methoxycarbonylvinyl)-2,2-dimethyloxazolidine-3-carboxylic Acid Tert-Butyl Ester (14)
3.2.4. (−)-(3S,4S)-4-Benzyl-5-(1-Hydroxymethylvinyl)-2-oxazolidinone (5)
3.3. Antibacterial Assays
3.3.1. Bacterial Strains and Culture Media
3.3.2. Antibacterial Screening Assay
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Diaz, G.; De Freitas, M.A.A.; Ricci-Silva, M.E.; Diaz, M.A.N. Easy Access to Evans’ Oxazolidinones. Stereoselective Synthesis and Antibacterial Activity of a New 2-Oxazolidinone Derivative. Molecules 2014, 19, 7429-7439. https://doi.org/10.3390/molecules19067429
Diaz G, De Freitas MAA, Ricci-Silva ME, Diaz MAN. Easy Access to Evans’ Oxazolidinones. Stereoselective Synthesis and Antibacterial Activity of a New 2-Oxazolidinone Derivative. Molecules. 2014; 19(6):7429-7439. https://doi.org/10.3390/molecules19067429
Chicago/Turabian StyleDiaz, Gaspar, Michelle A. A. De Freitas, Maria E. Ricci-Silva, and Marisa A. N. Diaz. 2014. "Easy Access to Evans’ Oxazolidinones. Stereoselective Synthesis and Antibacterial Activity of a New 2-Oxazolidinone Derivative" Molecules 19, no. 6: 7429-7439. https://doi.org/10.3390/molecules19067429