Novel 2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamides as antioxidant and/or anti-inflammatory compounds

•Novel N-thiazolyl/benzothiazolyl-thiazolidinedione-2-acetamides are prepared.•Essayed for DPPH RSA, SASA, LPI, EHI, IL-1β & MCP-1 secretion inhibition.•Some of them show both anti-inflammatory and antioxidant potential.•Structure of one of the target compounds is confirmed by X-ray.

A series of novel N-(4-aryl-1,3-thiazol-2-yl)-2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamides (4a–k) and N-(1,3-benzothiazol-2-yl)-2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamide derivatives (4l–o) are synthesized and evaluated for their anti-inflammatory and antioxidant activity (DPPH radical scavenging, superoxide anion scavenging, lipid peroxide inhibition, erythrocyte hemolytic inhibition). Compounds 4k and 4l have exhibited good antioxidant activity in four assays, while compounds 4c, 4d, 4m, 4n and 4o have shown good DPPH radical scavenging efficacy. Compounds 4a, 4h, 4i, 4k, 4m and 4n have possessed excellent anti-inflammatory activity. N-[4-(o-methoxyphenyl)-1,3-thiazol-2-yl]-2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamide (4k) and N-(6-nitro-/methoxy-1,3-benzothiazol-2-yl)-2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamide (4m and 4n) have exhibited both antioxidant and anti-inflammatory activities.

Graphical abstractA new series of N-thiazolyl-thiazolidinedione-2-acetamides are synthesized and evaluated for DPPH radical scavenging, SASA, LPI, EHI, IL-1β and MCP-1 secretion inhibition activities. Some of them have exhibited good antioxidant and anti-inflammatory potential.Figure optionsDownload full-size imageDownload as PowerPoint slide