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

Molecules

Veronika Opletalova¹  Jan Dolezel¹  Katarina Kralova¹  Matus Pesko¹  Jiri Kunes¹ 

[1] ¹Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic

关键词: rhodanine derivatives;    synthesis;    lipophilicity;    photosynthesis inhibition;    spinach chloroplasts;    Chlorella vulgaris;    structure-activity relationships;   

DOI  :  10.3390/molecules16065207

来源: mdpi

【 摘 要 】

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).

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.