title: Synthesis and antioxidant activity of 3-(Pyridin-2-ylmethyl)-1,3-thiazinan(thiazolidin)-4-ones.
abstract: 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.
authors.affiliation: Laboratório de Química Aplicada a Bioativos (LaQuiABio), Universidade Federal de Pelotas, Centro de Ciências Químicas, Farmacêuticas e de Alimentos (CCQFA), Campus Universitário, Pelotas, 96010-900, RS, Brazil.
authors.forename: Juliano
authors.initials: J
authors.lastname: Bosenbecker
authors.forename: Valéria D O
authors.initials: VD
authors.lastname: Bareño
authors.forename: Roberta
authors.initials: R
authors.lastname: Difabio
authors.forename: Flávia A
authors.initials: FA
authors.lastname: Vasconcellos
authors.forename: Filipe S P
authors.initials: FS
authors.lastname: Dutra
authors.forename: Pathise S
authors.initials: PS
authors.lastname: Oliveira
authors.forename: Alethéa G
authors.initials: AG
authors.lastname: Barschak
authors.forename: Francieli M
authors.initials: FM
authors.lastname: Stefanello
authors.forename: Wilson
authors.initials: W
authors.lastname: Cunico
mesh_terms: D000818:Animals; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015227:Lipid Peroxidation / Q000187:drug effects*; D051381:Rats; D017208:Rats, Wistar
chemical_list: D016166:Free Radical Scavengers; D006575:Heterocyclic Compounds, 3-Ring
keywords: Antioxidant; Cerebral cortex; Liver; Thiazinanones; Thiazolidinones