One–Pot Phosphate-Mediated Synthesis of Novel 1,3,5-Trisubstituted Pyridinium Salts: A New Family of S. aureus Inhibitors
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General Information and Methods
3.1.1. Chemistry
3.1.2. Biological Assays
Plate Zone Assays
Minimimal Inhibitory Concentration (MIC)
3.2. Procedure A for Synthesis of the 1,3,5-Substituted Pyridinium Salts
5. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of compounds 3 are available from the authors upon reasonable requests (where materials are available). |
Entry | Buffer | Yield of 3a |
---|---|---|
1 | KH2PO4 (KPi) | 48% |
2 | Glc-1-P | 40% |
3 | PPi | 23% |
4 | UMP | 53% |
5 | B(OH)3 | <1% |
6 | HEPES | 3% |
7 | Tris | <1% |
8 | water only | <1% |
Amine | R | Product | Isolated Yield | Amine | R | Product | Isolated Yield |
---|---|---|---|---|---|---|---|
6a | | 3a | 70% | 6h | | 3h | 65% |
6b | PhCH2CH2 | 3b | 54% | 6i | | 3i | 72% |
6c | | 3c | 52% | 6j | (CH2)6OH | 3j | 69% |
6d | | 3d | 38% | 6k | (CH2)3CO2H | 3k | 63% |
6e | | 3e | 50% | 6l | | 3l | 53% |
6f | | 3f | 45% | 6m | Ph | 3m | 0% |
6g | | 3g | 13% 2 | 6n | | 3n | 0% |
Aldehyde | R | Product | Yield |
---|---|---|---|
4a | PhCH2 | 3a | 70% |
4o | 4-HOC6H4CH2 | 3o | 66% |
4p | | 3p | 42% |
4q | 4-MeOC6H4CH2 | 3q | 58% |
4r | CH(CH3)2 | 3r (1r) 2 | 5(10)% |
4s | C2H5 | 3s | 0% |
Compound | 1 MIC (μg/mL) | Compound | 1 MIC (μg/mL) |
---|---|---|---|
3a | n.d. | 3h | 64 |
3b | 32 | 3i | n.d. |
3c | n.d. | 3j | 64 |
3d | 64 | 3k | n.d. |
3e | 16 | 3o | 32 |
3f | 64 | 3q | 32 |
3g | 16 | 3r | n.d. |
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Pesnot, T.; Gershater, M.C.; Edwards, M.; Ward, J.M.; Hailes, H.C. One–Pot Phosphate-Mediated Synthesis of Novel 1,3,5-Trisubstituted Pyridinium Salts: A New Family of S. aureus Inhibitors. Molecules 2017, 22, 626. https://doi.org/10.3390/molecules22040626
Pesnot T, Gershater MC, Edwards M, Ward JM, Hailes HC. One–Pot Phosphate-Mediated Synthesis of Novel 1,3,5-Trisubstituted Pyridinium Salts: A New Family of S. aureus Inhibitors. Molecules. 2017; 22(4):626. https://doi.org/10.3390/molecules22040626
Chicago/Turabian StylePesnot, Thomas, Markus C. Gershater, Martin Edwards, John M. Ward, and Helen C. Hailes. 2017. "One–Pot Phosphate-Mediated Synthesis of Novel 1,3,5-Trisubstituted Pyridinium Salts: A New Family of S. aureus Inhibitors" Molecules 22, no. 4: 626. https://doi.org/10.3390/molecules22040626