Synthesis of new curcumin derivatives as influential antidiabetic α-glucosidase and α-amylase inhibitors with anti-oxidant activity

• Published in: Carbohydrate research 2020-08, Vol.494, p.108069-108069, Article 108069
• Main Authors: Tavaf, Zohreh, Dangolani, Soheila Khajeh, Yousefi, Reza, Panahi, Farhad, Shahsavani, Mohammad Bagher, Khalafi-Nezhad, Ali
• Format: Article
• Language: English
• Subjects: alpha-Amylases - antagonists & inhibitors; alpha-Amylases - metabolism; alpha-Glucosidases - metabolism; Antibacterial activity; Antioxidant activity; Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; Curcumin - chemical synthesis; Curcumin - chemistry; Curcumin - pharmacology; Enzyme Inhibitors - chemical synthesis; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - pharmacology; Humans; Hypoglycemic Agents - chemical synthesis; Hypoglycemic Agents - chemistry; Hypoglycemic Agents - pharmacology; Inhibition; Microbial Sensitivity Tests; Molecular Docking Simulation; Molecular Structure; Saccharomyces cerevisiae - drug effects; Saccharomyces cerevisiae - enzymology; Saccharomyces cerevisiae - growth & development; α-Amylase; α-Glucosidase
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2020.108069

In this study, a new class of curcumin derivatives was synthesized using a multicomponent reaction containing curcumin, aldehydes, and malononitrile. This new protocol afforded a novel class of 4H-pyran heterocycles incorporating curcumin moiety. The products were obtained in the presence of p-toluenesulfonic acid (PTSA) as a catalyst in ethanol solvent in good to excellent yields. The synthetic compounds indicated a notable inhibitory activity against α-glucosidase (α-Gls) and revealed a weak inhibitory property against α–amylase (α-Amy). Also, these synthetic compounds indicated significant antioxidant activity. The new curcumin derivatives were also discovered to display no significant effect against the growth of two bacterial microflora in the human intestine. A molecular docking study was done to realize the binding interaction of the synthetic curcumin derivatives with the α-Gls enzyme. The results of our study introduced new synthetic curcumin derivatives as potential antidiabetic drugs. [Display omitted] •Synthesis a new class of curcumin derivatives using a multicomponent reaction.•A novel class of 4H-pyran heterocycles incorporating curcumin moiety.•A notable inhibitory activity of synthetic compounds against α-Gls.•Weak inhibitory property of new ligands against α-Amy.•Significant antioxidant activity of new curcumin derivatives.