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Photosynthesis-Inhibiting Activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides

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KOS Jiří GONĚC Tomáš ORAVEC Michal JENDRZEJEWSKA Izabela JAMPÍLEK Josef

Rok publikování 2021
Druh Článek v odborném periodiku
Časopis / Zdroj Molecules
Fakulta / Pracoviště MU

Farmaceutická fakulta

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.

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