Synthesis and characterization of (Z)-5-arylmethylidene-rhodanines with photosynthesis-inhibiting properties

• Published in: Molecules (Basel, Switzerland) Vol. 16; no. 6; pp. 5207 - 5227
• Main Authors: Opletalova, Veronika, Dolezel, Jan, Kralova, Katarina, Pesko, Matus, Kunes, Jiri, Jampilek, Josef
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 22.06.2011; MDPI
• Subjects: Chlorella vulgaris; Chlorella vulgaris - drug effects; Chlorella vulgaris - metabolism; Chlorophyll; Chloroplasts; Chloroplasts - drug effects; Chloroplasts - metabolism; Electron Transport - drug effects; Enzymes; Herbicides; Hydrophobic and Hydrophilic Interactions; lipophilicity; Nuclear Magnetic Resonance, Biomolecular; Organic chemistry; Pesticides; Pharmaceuticals; Pharmacy; Photosynthesis; Photosynthesis - drug effects; photosynthesis inhibition; Rhodanine - analogs & derivatives; Rhodanine - chemical synthesis; Rhodanine - pharmacology; rhodanine derivatives; spinach chloroplasts; Spinacia oleracea - drug effects; Spinacia oleracea - metabolism; structure-activity relationships; synthesis; Toxicity; Czech Republic; Slovakia
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules16065207

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 (IC(50) = 3.0 μmol/L) and the highest antialgal activity was exhibited by (5Z)-5-(4-chlorobenzylidene)-2-thioxo-1,3-thiazolidin-4-one (IC(50) = 1.3 μmol/L).