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

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

1,* , 1, 2, 3, 4 and 5,*
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 rhodanine derivatives; synthesis; lipophilicity; photosynthesis inhibition; spinach chloroplasts; Chlorella vulgaris; structure-activity relationships
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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