EventsThe 24th International Electronic Conference on Synthetic Organic Chemistry
Published
This submission belongs to the session B. Bioorganic, Medicinal and Natural Products Chemistry of the event The 24th International Electronic Conference on Synthetic Organic Chemistry
Published date
14 Nov, 2020
Citation
Josef Jampilek, Jiri Kos, Tomas Gonec, Michal Oravec, Photosynthesis-Inhibiting Activity of Methoxy-substituted 3-Hydroxynaphthalene-2-carboxanilides, in Proceedings of The 24th International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2020, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-24-08295
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Photosynthesis-Inhibiting Activity of Methoxy-substituted 3-Hydroxynaphthalene-2-carboxanilides

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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
Abstract

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
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