Investigation of the Anti-Methicillin-Resistant Staphylococcus aureus Activity of (+)-Tanikolide- and (+)-Malyngolide-Based Analogues Prepared by Asymmetric Synthesis
Abstract
:1. Introduction
2. Results
3. Conclusions
4. Materials and Methods—Chemistry
4.1. Ethyl 2-(diethoxyphosphoryl)undecanoate (10)
4.2. Ethyl 2-methyleneundecanoate (11)
4.3. 2-Methyleneundecan-1-ol (12)
4.4. (R)-(2-Nonyloxiran-2-yl)methanol (13)
4.5. (S)-2-[Benzyloxy)methyl]-2-undecyloxirane (14)
4.6. 2-(2-Bromopropyl)-1,3-dioxane (15)
4.7. (2S,4S)-4-((Benzyloxy)methyl)-1-(1,3-dioxan-2-yl)-2-methyltridecan-4-ol ((2S,4S)-18) & (2R,4S)-4-((benzyloxy)methyl)-1-(1,3-dioxan-2-yl)-2-methyltridecan-4-ol ((2R,4S)-22)
4.8. (2S,4R)-2-((Benzyloxy)methyl)-6-methoxy-4-methyl-2-nonyltetrahydro-2H-pyran (23/24)
4.9. (2S,4S)-2-((Benzyloxy)methyl)-6-methoxy-4-methyl-2-nonyltetrahydro-2H-pyran (19/20)
4.10. (4R,6S)-6-((Benzyloxy)methyl)-4-methyl-6-nonyltetrahydro-2H-pyran-2-one (25)
4.11. (4.S,6S)-6-((Benzyloxy)methyl)-4-methyl-6-nonyltetrahydro-2H-pyran-2-one (21)
4.12. (4. R,6S)-4-Methylmalyngolide (8)
4.13. (4S,6S)-4-Methylmalyngolide (7)
5. Materials and Methods—Biological Testing
5.1. Preparation of Compounds
5.2. Antibacterial Activity Testing—Determination of Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC)
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Compound | E. coli 25922 | E. coli 4 | MRSA ATCC 43300 | MRSA 06/04 | ||||
---|---|---|---|---|---|---|---|---|
MIC [b] | MBC | MIC | MBC | MIC | MBC | MIC | MBC | |
3 | >100 | >100 | >100 | >100 | >100 | >100 | >100 * | >100 |
4 | >100 | >100 | >100 | >100 | >100 | >100 | >100 * | >100 |
5 | >100 | >100 | >100 | >100 | 12.5 | 12.5 | 12.5 | 50 |
6 | >100 | >100 | >100 | >100 | >100 | >100 | >100 * | >100 |
Compound | E. coli 25922 | E. coli 4 | MRSA ATCC 43300 | MRSA 06/04 | ||||
---|---|---|---|---|---|---|---|---|
MIC [a] | MBC | MIC | MBC | MIC | MBC | MIC | MBC | |
7 | >100 | >100 | >100 | >100 | 50 | 50 | 50 | 50 |
8 | >100 | >100 | >100 | >100 | 50 | 100 | 50 | 50 |
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Breheny, J.; Kingston, C.; Doran, R.; Anes, J.; Martins, M.; Fanning, S.; Guiry, P.J. Investigation of the Anti-Methicillin-Resistant Staphylococcus aureus Activity of (+)-Tanikolide- and (+)-Malyngolide-Based Analogues Prepared by Asymmetric Synthesis. Int. J. Mol. Sci. 2021, 22, 6400. https://doi.org/10.3390/ijms22126400
Breheny J, Kingston C, Doran R, Anes J, Martins M, Fanning S, Guiry PJ. Investigation of the Anti-Methicillin-Resistant Staphylococcus aureus Activity of (+)-Tanikolide- and (+)-Malyngolide-Based Analogues Prepared by Asymmetric Synthesis. International Journal of Molecular Sciences. 2021; 22(12):6400. https://doi.org/10.3390/ijms22126400
Chicago/Turabian StyleBreheny, Joseph, Cian Kingston, Robert Doran, Joao Anes, Marta Martins, Séamus Fanning, and Patrick J. Guiry. 2021. "Investigation of the Anti-Methicillin-Resistant Staphylococcus aureus Activity of (+)-Tanikolide- and (+)-Malyngolide-Based Analogues Prepared by Asymmetric Synthesis" International Journal of Molecular Sciences 22, no. 12: 6400. https://doi.org/10.3390/ijms22126400