Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides †
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Lipophilicities
2.3. Inhibition of Photosynthetic Electron Transport (PET) in Spinach Chloroplasts
Comp. | R | log k | log P a | σ a | [μmol/L] | |||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
PET IC50 | MIC | LD50 | ||||||||||
SA | MRSA 63718 | MRSA 630 | MRSA 3202 | MM | MK | |||||||
1 | H | 0.6310 | 4.52 | 0 | b | >972 | >972 | >972 | >972 | 122 | 972 | – |
2a | 2-OCH3 | 0.6916 | 4.61 | −0.28 | 59.5 | 55.0 | 55.0 | 55.0 | 55.0 | 873 | 218 | >30 |
2b | 3-OCH3 | 0.6971 | 4.56 | 0.12 | 53.4 | >873 | >873 | >873 | >873 | >873 | 54.6 | >30 |
2c | 4-OCH3 | 0.5951 | 4.37 | −0.27 | b | >873 | >873 | >873 | >873 | >873 | 873 | – |
3a | 2-CH3 | 0.6936 | 4.85 | −0.17 | b | >923 | >923 | >923 | 462 | 462 | 115 | – |
3b | 3-CH3 | 0.8831 | 4.85 | −0.07 | b | >923 | >923 | >923 | 462 | 923 | 57.7 | >30 |
3c | 4-CH3 | 0.8753 | 4.85 | −0.17 | b | >923 | >923 | 462 | 231 | >923 | 923 | – |
4a | 2-F | 0.7303 | 4.56 | 0.06 | b | >910 | >910 | 455 | 228 | 28.4 | 56.9 | >30 |
4b | 3-F | 0.8296 | 4.69 | 0.34 | b | >910 | >910 | 455 | 228 | 114 | 114 | – |
4c | 4-F | 0.7317 | 4.70 | 0.06 | b | >910 | >910 | 455 | 228 | 910 | 114 | – |
5a | 2-Cl | 0.9509 | 5.02 | 0.22 | b | >860 | >860 | >860 | 215 | 860 | 860 | – |
5b | 3-Cl | 1.0796 | 5.25 | 0.37 | b | >860 | >860 | 430 | 215 | >860 | 860 | – |
5c | 4-Cl | 1.0687 | 5.24 | 0.23 | b | >860 | >860 | >860 | >860 | >860 | 430 | – |
6a | 2-Br | 0.9715 | 5.06 | 0.22 | 43.2 | >748 | >748 | >748 | >748 | >748 | 748 | – |
6b | 3-Br | 1.1536 | 5.39 | 0.39 | b | >748 | >748 | >748 | 187 | >748 | 748 | – |
6c | 4-Br | 1.1459 | 5.28 | 0.23 | b | >748 | >748 | >748 | 187 | >748 | 374 | – |
7a | 2-CF3 | 0.8762 | 5.42 | 0.51 | 105.2 | >773 | >773 | >773 | 97 | 193 | 193 | 28.6 ± 0.5 |
7b | 3-CF3 | 1.2053 | 5.49 | 0.43 | b | >748 | >748 | 374 | 187 | >748 | 748 | – |
7c | 4-CF3 | 1.2835 | 5.33 | 0.51 | b | >748 | >748 | 374 | 187 | >748 | 187 | – |
8a | 2-NO2 | 0.8710 | 4.51 | 0.77 | 106.6 | >830 | >830 | 415 | 415 | 830 | 830 | – |
8b | 3-NO2 | 0.8143 | 4.64 | 0.71 | 16.9 | >830 | >830 | >830 | >830 | >830 | 415 | 2.5 ± 0.9 |
8c | 4-NO2 | 0.9175 | 4.65 | 0.78 | 187.5 | >830 | >830 | >830 | >830 | >830 | 13.0 | <0.37 |
DCMU | – | – | – | 1.9 | – | – | – | – | – | – | – | |
APC | – | – | – | 5.7 | >45.8 | >45.8 | >45.8 | – | – | – | ||
INH | – | – | – | – | 467 | 29.2 | – |
2.4. In Vitro Antibacterial Susceptibility Testing
2.5. In Vitro Antimycobacterial Evaluation
2.6. In Vitro Cytotoxicity Assay
3. Experimental
3.1. General
3.2. Synthesis
3.2.1. General Procedure for Synthesis of Carboxamide Derivatives 1–8c
3.3. Lipophilicity Determination by HPLC (Capacity Factor k/Calculated log k)
3.4. Study of Inhibition of Photosynthetic Electron Transport (PET) in Spinach Chloroplasts
3.5. Study of Chlorophyll a Fluorescence in Spinach Chloroplasts
3.6. In Vitro Antibacterial Susceptibility Testing
3.7. In Vitro Antimycobacterial Evaluation
3.8. In Vitro Cytotoxicity Assay
4. Conclusions
Acknowledgments
Conflicts of Interest
References
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Kos, J.; Zadrazilova, I.; Pesko, M.; Keltosova, S.; Tengler, J.; Gonec, T.; Bobal, P.; Kauerova, T.; Oravec, M.; Kollar, P.; et al. Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides. Molecules 2013, 18, 7977-7997. https://doi.org/10.3390/molecules18077977
Kos J, Zadrazilova I, Pesko M, Keltosova S, Tengler J, Gonec T, Bobal P, Kauerova T, Oravec M, Kollar P, et al. Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides. Molecules. 2013; 18(7):7977-7997. https://doi.org/10.3390/molecules18077977
Chicago/Turabian StyleKos, Jiri, Iveta Zadrazilova, Matus Pesko, Stanislava Keltosova, Jan Tengler, Tomas Gonec, Pavel Bobal, Tereza Kauerova, Michal Oravec, Peter Kollar, and et al. 2013. "Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides" Molecules 18, no. 7: 7977-7997. https://doi.org/10.3390/molecules18077977