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.

Synthesis of Six and Seven-membered Heterocyclic Molecules Containing an Adamantyl Fragment and an X-ray Crystal Structure of (E)-N-(adamantan-1-yl)-1-(3-nitrophenyl)methanimine

“…Thiazine, oxazine and oxazepine have similar structures for six and seven-membered heterocyclic compounds which contain two hetero atoms (S, N) and (O, N), respectively (14)(15)(16). Oxazepinone is synthesized via a cyclo-addition reaction (2+5) between imine and anhydride (17)(18)(19)(20).…”

“…Oxazepinone is synthesized via a cyclo-addition reaction (2+5) between imine and anhydride (17)(18)(19)(20). Whereas, thiazinanone prepared via the condensation of pyridin-2-ylmethanamine, benzaldehyde derivatives, and 3-mercaptopropanoic acid (14,20). The reaction between imine and glycolic acid gave oxazinone (21).…”

Synthesis of Novel Thiazolidin‐4‐ones and Thiazinan‐4‐ones Analogous to Rosiglitazone

“…Numerous studies describe a wide range of pharmacological properties of thiazolidinones: anti‐HCV, anti‐HIV, antitumoral, antifungal, tuberculostatic, and antioxidant . Thiazinanones (six‐membered heterocycle) are less common in the literature; however, they also show major biological properties as immune potentiating, anti‐inflammatory, antimalarial, and antibacterial agents .…”

Synthesis of Novel 2-Aryl-3-(2-morpholinoethyl)-1,3-thiazinan-4-ones Via Ultrasound Irradiation

“…Six-membered thiazinanones show important biological properties as antioxidant, anti-inflammatory, anti-diabetic and antimicrobial. [15][16][17][18] The strategies to the synthesis of thiazinanones are quite similar to the strategies to the synthesis of analogue five-membered thiazolidinones. Thus, thiazinanones could be obtained by a multicomponent reaction between a primary amine, an aldehyde (or ketone) and the mercaptopropionic acid 15,17,19 or by a reaction between thioureas and β-propylhaloacetic acid.…”

“…[15][16][17][18] The strategies to the synthesis of thiazinanones are quite similar to the strategies to the synthesis of analogue five-membered thiazolidinones. Thus, thiazinanones could be obtained by a multicomponent reaction between a primary amine, an aldehyde (or ketone) and the mercaptopropionic acid 15,17,19 or by a reaction between thioureas and β-propylhaloacetic acid. 18 Moreover, these methods can be applied in two steps, multicomponent (all reactants together in the beginning of reaction) or onepot reactions, under catalysis or not.…”