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Photosynthesis-Inhibiting Activity of Methoxy-substituted 3-Hydroxynaphthalene-2-carboxanilides
1 , 2 , 3 , * 4, 5
1  Division of Biologically Active Complexes and Molecular Magnets, Regional Centre of Advanced Technologies and Materials, Faculty of Science, Palacky University, Slechtitelu 27, 78371 Olomouc, Czech Republic
2  Department of Chemical Drugs, Faculty of Pharmacy, Masaryk University, Palackeho 1, 602 00 Brno, Czech Republic
3  Global Change Research Institute CAS, Belidla 986/4a, 603 00 Brno, Czech Republic
4  Department of Analytical Chemistry, Faculty of Natural Sciences, Comenius University, Ilkovicova 6, 84215 Bratislava, Slovakia
5  Institute of Neuroimmunology, Slovak Academy of Sciences, Dubravska Cesta 9, 845 10 Bratislava, Slovakia


In this study a series of six 3-hydroxynaphthalene-2-carboxanilides, substituted on the anilide ring by combinations of methoxy-methoxy, methoxy-fluoro and methoxy-chloro groups at different positions, was prepared by microwave-assisted synthesis and characterized. The compounds were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The PET-inhibiting activity of the compounds was within a wide range, but rather moderate; the highest activity within the series of the compounds was determined for N-(3,5-dimehoxyphenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 24.5 µM). The compounds were found to inhibit PET in photosystem II.

Keywords: Hydroxynaphthalene-carboxamides; PET inhibition; Spinach chloroplasts; Structure-activity relationships