| Summary: | The 5-acetyl-2-aryl-6-hydroxybenzo[<i>b</i>]furans <b>2a</b>−<b>h</b> have been evaluated through in vitro enzymatic assay against targets which are linked to type 2 diabetes (T2D), namely, α-glucosidase, protein tyrosine phosphatase 1B (PTP1B) and β-secretase. These compounds have also been evaluated for antioxidant activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging method. The most active compounds against α-glucosidase and/or PTP1B, namely, 4-fluorophenyl <b>2c</b>, 4-methoxyphenyl <b>2g</b> and 3,5-dimethoxyphenyl substituted <b>2h</b> derivatives were also evaluated for potential anti-inflammatory properties against cyclooxygenase-2 activity. The Lineweaver-Burk and Dixon plots were used to determine the type of inhibition on compounds <b>2c</b> and <b>2h</b> against α-glucosidase and PTP1B receptors. The interactions were investigated in modelled complexes against α-glucosidase and PTP1B via molecular docking.
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