title: Synthesis and characterization of (Z)-5-arylmethylidene-rhodanines with photosynthesis-inhibiting properties.
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 (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).
authors.affiliation: 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. veronika.opletalova@faf.cuni.cz
authors.forename: Veronika
authors.initials: V
authors.lastname: Opletalova
authors.forename: Jan
authors.initials: J
authors.lastname: Dolezel
authors.forename: Katarina
authors.initials: K
authors.lastname: Kralova
authors.forename: Matus
authors.initials: M
authors.lastname: Pesko
authors.forename: Jiri
authors.initials: J
authors.lastname: Kunes
authors.forename: Josef
authors.initials: J
authors.lastname: Jampilek
mesh_terms: D048408:Chlorella vulgaris / Q000187:drug effects / Q000378:metabolism; D002736:Chloroplasts / Q000187:drug effects / Q000378:metabolism; D004579:Electron Transport / Q000187:drug effects; D057927:Hydrophobic and Hydrophilic Interactions; D019906:Nuclear Magnetic Resonance, Biomolecular; D010788:Photosynthesis / Q000187:drug effects*; D012236:Rhodanine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D018724:Spinacia oleracea / Q000187:drug effects / Q000378:metabolism
chemical_list: D012236:Rhodanine