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 ~ 10 µM) 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.

Department of Analytical Chemistry Faculty of Natural Sciences Comenius University Ilkovicova 6 84215 Bratislava Slovakia

Department of Biochemistry Faculty of Medicine Masaryk University Kamenice 5 62500 Brno Czech Republic

Department of Chemical Drugs Faculty of Pharmacy Masaryk University Palackeho tr 1946 1 61200 Brno Czech Republic

Global Change Research Institute of the Czech Academy of Sciences Belidla 986 4a 60300 Brno Czech Republic

Institute of Chemistry University of Silesia Szkolna 9 40007 Katowice Poland

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