Contract Grant Sponsor: UFPel. Contract Grant Sponsor: CNPq. Contract Grant Numbers: proc. 557373/2010-7 and proc. 507690/2010-9. Contract Grant Sponsor: FAPERGS. Contract Grant Number: proc. 1015636.
Synthesis and Antioxidant Activity of 3-(Pyridin-2-ylmethyl)-1,3-thiazinan(thiazolidin)-4-ones
Article first published online: 17 JUN 2014
© 2014 Wiley Periodicals, Inc.
Journal of Biochemical and Molecular Toxicology
Volume 28, Issue 9, pages 425–432, September 2014
How to Cite
Bosenbecker, J., Bareño, V. D.O., Difabio, R., Vasconcellos, F. A., Dutra, F. S.P., Oliveira, P. S., Barschak, A. G., Stefanello, F. M. and Cunico, W. (2014), Synthesis and Antioxidant Activity of 3-(Pyridin-2-ylmethyl)-1,3-thiazinan(thiazolidin)-4-ones. J. Biochem. Mol. Toxicol., 28: 425–432. doi: 10.1002/jbt.21581
- Issue published online: 4 SEP 2014
- Article first published online: 17 JUN 2014
- Manuscript Accepted: 13 MAY 2014
- Manuscript Revised: 9 MAY 2014
- Manuscript Received: 7 APR 2014
- CNPq. Grant Numbers: proc. 557373/2010-7, proc. 507690/2010-9
- FAPERGS. Grant Number: proc. 1015636
- Cerebral cortex;
The antioxidant properties of two series of thiazolidinones and thiazinanones were reported. The novel six-membered thiazinanones were synthesized from the efficient multicomponent reaction of 2-picolylamine (2-aminomethylpyridine), arenaldehydes, and the 3-mercaptopropionic acid in moderate to excellent yields. These novel compounds were fully identified and characterized by NMR and GC-MS techniques. In vitro antioxidant activities of all compounds were evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) tests. The antioxidant assays of thiobarbituric acid reactive species and total thiol content levels in the cerebral cortex and liver of rats were also performed. Thiazinanone 5a showed the best radical scavenging activity in DPPH and ABTS tests, as well as reduced lipid peroxidation and increased total thiol group in biological systems. Altogether, the results may be considered a good starting point for the discovery of a new radical scavenger.