Synthesis and biological evaluation of novel 2-heteroarylimino-1,3-thiazolidin-4-ones as potential anti-tumor agents

A series of 35 heteroarylimino-1,3-thiazolidinones with three sites of functionalization were synthesized and their antiproliferative properties were studied. The in vitro screening by MTT assay was performed against five cancer cell lines (human colon cancer cell lines HT29, HCT116 and SW620 and br...

Full description

Saved in:
Bibliographic Details
Published in:European journal of medicinal chemistry 2015-04, Vol.94, p.102-112
Main Authors: Revelant, Germain, Huber-Villaume, Sophie, Dunand, Sandrine, Kirsch, Gilbert, Schohn, Hervé, Hesse, Stéphanie
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antiproliferative activity
Autophagy - drug effects
Cell Cycle - drug effects
Cell Line, Tumor
Chemical Sciences
Chemistry Techniques, Synthetic
Colon cancer
Drug Screening Assays, Antitumor
Humans
Inhibitory Concentration 50
Membrane Potential, Mitochondrial - drug effects
Oxidation-Reduction
Structure-Activity Relationship
Thiazole
Thiazolidines - chemistry
Thiazolidinone
Thiophene
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A series of 35 heteroarylimino-1,3-thiazolidinones with three sites of functionalization were synthesized and their antiproliferative properties were studied. The in vitro screening by MTT assay was performed against five cancer cell lines (human colon cancer cell lines HT29, HCT116 and SW620 and breast cancer cell lines MCF7 and MDA-MB-231). It was observed that N3-substituted thiazolidinones had moderate activities whereas 5-benzylidene thiazolidinones showed promising activities. To investigate the mechanism of action, detailed biological studies of six selected compounds (those presenting the lower mitotic index) were carried out on the human colon cancer HT29 cell line. Cell cycle assay revealed that those compounds induced cell accumulation in G2/M and in subG0/G1 phases of cell cycle. Moreover, dissipation of mitochondria membrane potential was observed as well as redox changes in treated cells. [Display omitted] •35 Heteroaryliminothiazolidinones were synthesized.•Their antiproliferative properties were investigated.•Benzylidene moiety on 5-position of the thiazolidinone gave more potent compounds.•Derivatives with a thiazolylimino moiety showed promising cytotoxicity.•Accumulation in G2/M phase and in subG1 fraction was observed.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2015.02.053