Preliminary Study of Photosynthesis-Inhibiting Activity of Substituted Phenylcarbamoylphenyl N-alkylcarbamates

Jarmila Vinsova; Juana Ferriz; Katarina Kralova; Matus Pesko; Josef Jampilek; Ales Imramovsky

doi:10.3390/ecsoc-14-00375

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Substituted N-phenylpyrazine-2-carboxamides, Their Synthesis, Hydro-lipophilic Properties and Evaluation of Their Antimycobacterial, Antifungal and Photosynthesis-inhibiting Activity

Preliminary Study of Photosynthesis-Inhibiting Activity of Substituted Phenylcarbamoylphenyl N-alkylcarbamates

Jarmila Vinsova

¹,

Juana Monreal Ferriz

¹,

Katarina Kralova

²,

Matus Pesko

³,

Josef Jampilek

^{*

4, 5},

Ales Imramovsky

^{*

6}

¹ Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, 500 05 Hradec Kralove, Czech Republic
² Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia
³ Department of Ecosozology and Physiotactics, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia
⁴ Zentiva a.s., U kabelovny 130, 102 37 Prague 10, Czech Republic
⁵ Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
⁶ Institute of Organic Chemistry and Technology, Faculty of Chemistry and Chemical Technology, University of Pardubice, Studentska 573, 532 10 Pardubice, Czech Republic

Published: 22 October 2010 by MDPI in The 14th International Electronic Conference on Synthetic Organic Chemistry session Natural Products Chemistry

https://doi.org/10.3390/ecsoc-14-00375

Abstract: In this study, a series of nine 4-chloro-2-(3,4-dichlorophenylcarbamoyl)phenyl N-alkylcarbamates was prepared. The procedures for synthesis of the compounds are presented. The compounds were analyzed using RP-HPLC to determine lipophilicity. They were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. For the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds are discussed, as well as their structure-activity relationships (SAR).

Keywords: 4-Chloro-2-(3,4-dichlorophenylcarbamoyl)-phenyl N-alkylcarbamates; Lipophilicity; PET inhibition; Spinach chloroplasts; Structure-activity relationships

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Jarmila Vinsova

Juana Ferriz

Katarina Kralova

Matus Pesko

Josef Jampilek

Ales Imramovsky