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Photosynthesis-Inhibiting Activity of Fluorinated 2‑Hydroxynaphthalene-1-carboxanilides
* 1 , 2 , * 3, 4
1  Department of Chemical Drugs, Faculty of Pharmacy, Masaryk University, Palackeho 1946/1, 612 00 Brno, Czech Republic
2  Global Change Research Institute of the Czech Academy of Sciences, Belidla 986/4a, 60300 Brno, Czech Republic
3  Department of Analytical Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, 84215 Bratislava, Slovakia
4  Institute of Neuroimmunology, Slovak Academy of Sciences, Dubravska Cesta 9, 845 10 Bratislava, Slovakia
Academic Editor: Julio A. Seijas

Abstract:

2-Hydroxy-N-phenylnaphthalene-1-carboxamide, three fluoro monosubstituted and five fluoro disubstituted 2-hydroxynaphthalene-1-carboxanilides were prepared by microwave-assisted synthesis and characterized. All the compounds were evaluated for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The PET inhibitory activity of the discussed compounds proved to be in a wide range, from inactive N-(2,6-difluorophenyl)-2-hydroxynaphthalene-1-carboxamide with an IC50 = 904 μM to N-(2,5-difluorophenyl)-2-hydroxynaphthalene-1-carboxamide with an IC50 of 44.2 μM, which was the most potent isomer of the series of evaluated compounds. Based on previous studies, it can be assumed that the mechanism of PET inhibition of these compounds is the inhibition of photosystem II in the thylakoid membrane.

Keywords: Hydroxynaphthalene-carboxamides; PET inhibition; Spinach chloroplasts
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