Abstract
In the present research work, ten novel thiazolidine-2,4-dione-coumarin adducts were synthesized using three step reaction procedure. Firstly, benzylidene thiazolidinediones (II) were synthesized by facile Knoevenagel condensation reaction using various substituted aldehydes, thiourea and chloroacetic acid. Further, 3-bromoacetyl coumarins (IV) were synthesized using salicylaldehyde and ethylacetoacetate in the presence of piperidine as a catalyst forming 3-acetylcoumarin (III) which was brominated to form 3- bromoacetyl coumarin. Finally, both these compounds i.e., (II) and (IV) were condensed in the presence of dimethyl formamide and potassium carbonate leading to the formation of novel thiazolidine-2,4-dione-coumarin adducts. The synthesized compounds were screened for different biological activities. Antioxidant activity was performed in-vitro by three different methods namely FRAP (Ferric ion reducing antioxidant power) method, DPPH (1,1-diphenyl-2-picrylhydrazyl) method and hydrogen peroxide scavenging assay method using ascorbic acid as a standard. Among the synthesized compounds, FP10 and FP9 emerged as breakthrough antioxidant agents. Furthermore, the compounds were checked for their anti-inflammatory and antidiabetic activity in which compounds FP7 and FP1 showed promising anti-inflammatory and antidiabetic potential in-vivo, and may be used as lead compound for future studies.
Keywords: Antidiabetic, Antiinflammatory, Antioxidant, Coumarin, Knoevenagel condensation, Thiazolidinedione.
Graphical Abstract
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