Events The 18th International Electronic Conference on Synthetic Organic Chemistry

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Published

This submission belongs to the session b. Bioorganic, Medicinal and Natural Products Chemistry of the event The 18th International Electronic Conference on Synthetic Organic Chemistry

Published date

31 Oct, 2014

Citation

Tomas Gonec, Jiri Kos, Michal Stujber, Matus Pesko, Michal Oravec, Tibor Liptaj, Katarina Kralova, Josef Jampilek, Preparation and Photosynthesis-Inhibiting Activity of N-(n-Alkoxy)phenylamides of 2-Hydroxynaphthalene-1-carboxylic acid, in Proceedings of The 18th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2014, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-18-b010

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

Tomas Gonec ¹

Jiri Kos ¹

Michal Stujber ²

Matus Pesko ³

Michal Oravec ⁴

Tibor Liptaj ²

Katarina Kralova ⁵

Josef Jampilek ¹

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

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

Manuscript

ECSOC-18_Preparation and Photosynthesis-Inhibiting Activity.pdf

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