Molecules 2011, 16(6), 5207-5227; doi:10.3390/molecules16065207
Article

Synthesis and Characterization of (Z)-5-Arylmethylidene-rhodanines with Photosynthesis-Inhibiting Properties

1 Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic 2 Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia 3 Department of Ecosozology and Physiotactics, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia 4 Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic 5 Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic
Preliminary results related to the topic of this article were presented at The Eleventh Electronic Conference on Synthetic Organic Chemistry (ECSOC-11, http://www.usc.es/congresos/ecsoc/11/hall_aGOS/a012/index.htm), November 1-30, 2007.
* Authors to whom correspondence should be addressed.
Received: 16 May 2011; in revised form: 15 June 2011 / Accepted: 21 June 2011 / Published: 22 June 2011
(This article belongs to the Special Issue ECSOC-11)
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Abstract: A series of rhodanine derivatives was prepared. The synthetic approach, analytical and spectroscopic data of all synthesized compounds are presented. Lipophilicity of all the discussed rhodanine derivatives was analyzed using the RP-HPLC method. The compounds were tested for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts and reduce chlorophyll content in freshwater alga Chlorella vulgaris. Structure-activity relationships between the chemical structure, physical properties and biological activities of the evaluated compounds are discussed. For majority of the tested compounds the lipophilicity of the compound and not electronic properties of the R1 substituent were decisive for PET-inhibiting activity. The most potent PET inhibitor was (5Z)-5-(4-bromobenzylidene)-2-thioxo-1,3-thiazolidin-4-one (IC50 = 3.0 μmol/L) and the highest antialgal activity was exhibited by (5Z)-5-(4-chlorobenzylidene)-2-thioxo-1,3-thiazolidin-4-one (IC50 = 1.3 μmol/L).
Keywords: rhodanine derivatives; synthesis; lipophilicity; photosynthesis inhibition; spinach chloroplasts; Chlorella vulgaris; structure-activity relationships

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MDPI and ACS Style

Opletalova, V.; Dolezel, J.; Kralova, K.; Pesko, M.; Kunes, J.; Jampilek, J. Synthesis and Characterization of (Z)-5-Arylmethylidene-rhodanines with Photosynthesis-Inhibiting Properties. Molecules 2011, 16, 5207-5227.

AMA Style

Opletalova V, Dolezel J, Kralova K, Pesko M, Kunes J, Jampilek J. Synthesis and Characterization of (Z)-5-Arylmethylidene-rhodanines with Photosynthesis-Inhibiting Properties. Molecules. 2011; 16(6):5207-5227.

Chicago/Turabian Style

Opletalova, Veronika; Dolezel, Jan; Kralova, Katarina; Pesko, Matus; Kunes, Jiri; Jampilek, Josef. 2011. "Synthesis and Characterization of (Z)-5-Arylmethylidene-rhodanines with Photosynthesis-Inhibiting Properties." Molecules 16, no. 6: 5207-5227.

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