Synthesis and biological evaluation of 5-benzylidenerhodanine-3-acetic acid derivatives as AChE and 15-LOX inhibitors

Abstract

A series of 5-benzylidenerhodanine-3-acetamides bearing morpholino-, 4-arylpiperazinyl-, or 4-benzylpiperidinyl- moieties were synthesized and their inhibitory activities against acetylcholinesterase (AChE) were evaluated. Alteration of amide part and substitution on the benzylidene moiety resulted in change of anti-AChE activity. The most active compound was the 1-benzylpiperidinyl derivative containing 4-(dimethylamino)benzylidene scaffold. Notably, the intermediate compounds, namely 5-arylidene-rhodanine-3-acetic acids (3), showed mild inhibitory activity against 15-lipoxygenase (15-LOX), while the final compound 4 showed no activity against 15-LOX.

• 2-Thioxothiazolidin-4-one
• 15-lipoxygenase
• acetylcholinesterase
• docking study
• inhibitors
• rhodanines

Acknowledgements

Chimera is developed by the 25 Resource for Biocomputing, Visualization, and Informatics at the University of California, San Francisco.

Declaration of interest

The authors have declared no conflict of interest.

The work was supported by grant from International Campus, Tehran University of Medical Sciences.

Supplementary material available online

Supplementary Figures.