Synthesis and Antimicrobial Activity of Novel 4-Hydroxy-2-quinolone Analogs
Abstract
:1. Introduction
2. Results and Discussions
2.1. Chemical Synthesis
2.2. Antimicrobial Activity and Structure–Activity Relationship
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Synthesis of Compounds 1a–1g
3.3. Synthesis of Compounds 2a and 2b
3.4. Synthesis of Compounds 3a–3j, 4d, and 5d
3.5. Evaluation of Antibacterial Activity
3.6. Evaluation of Antifungal Activity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 3a–3j and 4d are available from the authors. |
Compound | Substituents | IC50 1 (µg/mL) | MIC 2 (µg/mL) | |||
---|---|---|---|---|---|---|
R 1 | R 2 | R 3 | A. flavus | S. aureus | E. coli | |
3a | tridecyl | H | Me | 70.97 ± 3.71 | >1000 | >1000 |
3b | tridecyl | 6-OCH3 | Me | 42.15 ± 18.61 | >1000 | >1000 |
3c | tridecyl | 7-Cl | Me | 14.72 ± 2.35 | >1000 | >1000 |
3d | tridecyl | 7-NO2 | Me | 38.45 ± 5.51 | >1000 | >1000 |
3e | tridecyl | 6-Cl | Me | 37.08 ± 1.52 | >1000 | >1000 |
3f | tridecyl | 6-Br | Me | 23.19 ± 3.19 | >1000 | >1000 |
3g | tridecyl | H | Et | 9.48 ± 6.17 | >1000 | >1000 |
3h | nonyl | H | Me | 8.45 ± 1.59 | >1000 | >1000 |
3i | nonyl | 6-Cl | Me | 4.60 ± 1.14 | * | >1000 |
3j | nonyl | 6-Br | Me | 1.05 ± 1.31 | ** | >1000 |
4d3 | tridecyl 3 | 7-NO2 3 | Me 3 | 23.44 ± 1.63 | >1000 | >1000 |
AMB 4 | – | – | – | 1.93 ± 1.04 | ND | ND |
CIP 5 | – | – | – | ND | 0.835 | 0.0288 |
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Khamkhenshorngphanuch, T.; Kulkraisri, K.; Janjamratsaeng, A.; Plabutong, N.; Thammahong, A.; Manadee, K.; Na Pombejra, S.; Khotavivattana, T. Synthesis and Antimicrobial Activity of Novel 4-Hydroxy-2-quinolone Analogs. Molecules 2020, 25, 3059. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25133059
Khamkhenshorngphanuch T, Kulkraisri K, Janjamratsaeng A, Plabutong N, Thammahong A, Manadee K, Na Pombejra S, Khotavivattana T. Synthesis and Antimicrobial Activity of Novel 4-Hydroxy-2-quinolone Analogs. Molecules. 2020; 25(13):3059. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25133059
Chicago/Turabian StyleKhamkhenshorngphanuch, Thitiphong, Kittipat Kulkraisri, Alongkorn Janjamratsaeng, Napasawan Plabutong, Arsa Thammahong, Kanitta Manadee, Sarisa Na Pombejra, and Tanatorn Khotavivattana. 2020. "Synthesis and Antimicrobial Activity of Novel 4-Hydroxy-2-quinolone Analogs" Molecules 25, no. 13: 3059. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25133059