Preparation and Biological Properties of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides

Jiri Kos; Iveta Zadrazilova; Matus Pesko; Jiri Pavlica; Tomas Gonec; Pavel Bobal; Michal Oravec; Alois Cizek; Katarina Kralova; Josef Jampilek

doi:10.3390/ecsoc-16-01009

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Preparation and Biological Properties of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides

Jiri Kos

¹,

Iveta Zadrazilova

^{1, 2},

Matus Pesko

³,

Jiri Pavlica

¹,

Tomas Gonec

¹,

Pavel Bobal

¹,

Michal Oravec

⁴,

Alois Cizek

²,

Katarina Kralova

⁵,

Josef Jampilek

^{*

1, 6}

¹ Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
² Department of Infectious Diseases and Microbiology, Faculty of Veterinary Medicine, University of Veterinary and Pharmaceutical Sciences, Palackého 1/3, 612 42 Brno, Czech Republic
³ Department of Ecosozology and Physiotactics, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 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, 84215 Bratislava, Slovakia
⁶ Research Institute for Pharmacy and Biochemistry, Lidicka 1879/48, 602 00 Brno, Czech Republic

Published: 30 October 2012 by MDPI in The 16th International Electronic Conference on Synthetic Organic Chemistry session Bioorganic, Medicinal and Natural Products

https://doi.org/10.3390/ecsoc-16-01009

Abstract: In this study a series of twenty-five ring-substituted 3-hydroxy-N-phenylnaphthalene-2-carboxanilides were prepared. The procedures for synthesis of the compounds are presented. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four Staphylococcus strains. Several compounds showed noteworthy biological activity especially against methicillin-resistant Staphylococcus aureus strains. For all the compounds structure-activity relationships (SAR) are discussed.

Keywords: Naphthalene-2-carboxanilides; PET inhibition; Spinach chloroplasts; Staphylococcus aureus; Structure-activity relationships

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