Preparation and Photosynthesis-Inhibiting Activity of N-(n-Alkoxy)phenylamides of 2-Hydroxynaphthalene-1-carboxylic acid

¹ Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic
² Department of NMR Spectroscopy and Mass Spectrometry, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinskeho 9, 812 37 Bratislava, Slovakia
³ Department of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia
⁴ Global Change Research Centre AS CR, Belidla 986/4a, 603 00 Brno, Czech Republic
⁵ Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia

Published: 31 October 2014 by MDPI in The 18th International Electronic Conference on Synthetic Organic Chemistry session Bioorganic, Medicinal and Natural Products Chemistry

https://doi.org/10.3390/ecsoc-18-b010

Abstract: In this study a series of twelve n-alkoxy-substituted 2-hydroxynaphthalene-1-carboxanilides was prepared and characterized. The discussed compounds were prepared by microwave-assisted synthesis. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The highest PET inhibition was observed for meta-substituted compounds, whereas 2-hydroxy-N-(3-propoxyphenyl)naphthalene-1-carboxamide showed the highest PET inhibition within the whole series. In spite of medium or moderate PET-inhibiting activity it was found that the compounds inhibit PET in photosystem II. The activity of all positional isomers is strongly influenced by lipophilicity and the length/bulkiness of the alkoxy chain.

Keywords: Hydroxyquinoline-1-carboxamides; PET inhibition; spinach chloroplasts; structure-activity relationships

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