Investigation of the Biological Properties of (Hetero)Aromatic Thiosemicarbazones

Molecules

Maciej Serda¹  Anna Mrozek-Wilczkiewicz¹  Josef Jampilek¹  Matus Pesko¹  Katarina Kralova¹  Marcela Vejsova¹  Robert Musiol¹  Alicja Ratuszna¹ 

[1] ¹Department of Organic Chemistry, Institute of Chemistry, University of Silesia, PL-40006 Katowice, Poland

关键词: thiosemicarbazones;    lipophilicity;    photosynthetic electron transport inhibition;    spinach chloroplasts;    iron chelators;    in vitro antifungal activity;    in vitro anticancer activity;   

DOI  :  10.3390/molecules171113483

来源: mdpi

【 摘 要 】

Two series of thiosemicarbazone-based iron chelators (twenty-seven compounds) were designed and synthesized using a microwave-assisted approach. Quinoline and halogenated phenyl were selected as parent scaffolds on the basis of a similarity search. The lipophilicity of the synthesized compounds was measured using HPLC and then calculated. Primary in vitro screening of the synthesized compounds was performed against eight pathogenic fungal strains. Only a few compounds showed moderate activity against fungi, and (E)-2-(quinolin-2-ylvinyl)-N,N-dimethylhydrazine-carbothioamide appeared to be more effective than fluconazole against most of the fungal strains tested. Antiproliferative activity was measured using a human colon cancer cell line (HCT-116). Several of the tested compounds showed submicromolar antiproliferative activity. Compounds were also tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The structure-activity relationships are discussed for all of the compounds.

【 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.