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Photosynthesis-Inhibiting Activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides
Autoři | |
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Rok publikování | 2021 |
Druh | Článek v odborném periodiku |
Časopis / Zdroj | Molecules |
Fakulta / Pracoviště MU | |
Citace | |
www | Odkaz na plný text výsledku nebo domovskou stránku výsledku. |
Doi | http://dx.doi.org/10.3390/molecules26144336 |
Klíčová slova | hydroxynaphthalene-carboxamides; PET inhibition; spinach chloroplasts; structure-activity relationships |
Popis | A set of twenty-four 3-hydroxynaphthalene-2-carboxanilides, disubstituted on the anilide ring by combinations of methoxy/methyl/fluoro/chloro/bromo and ditrifluoromethyl groups at different positions, was prepared. The compounds were tested for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3,5-Difluorophenyl)-, N-(3,5-dimethylphenyl)-, N-(2,5-difluorophenyl)- and N-(2,5-dimethylphenyl)-3-hydroxynaphthalene-2-carboxamides showed the highest PET-inhibiting activity (IC50 similar to 10 mu M) within the series. These compounds were able to inhibit PET in photosystem II. It has been found that PET-inhibiting activity strongly depends on the position of the individual substituents on the anilide ring and on the lipophilicity of the compounds. The electron-withdrawing properties of the substituents contribute towards the PET activity of these compounds. |