Design, synthesis and in silico evaluation of benzoxazepino(7,6-b)quinolines as potential antidiabetic agents

AbstractThe second-generation XPhos palladium preformed catalyst-based C –N cross-coupling through Buchwald–Hartwig amination with primary and secondary amines towards functionalized benzoxazepino(7,6-b)quinolines is accounted for. The microwave irradiation in dioxane provided the desired highly functionalized oxazepino quinolines,5, in high yield and purity from the corresponding 2-chloro-3-formyl quinolines,1, via intermediate,4, in a sequential cyclization/Buchwald amination strategy. Besides, functional group tolerance, low catalyst loading, microwave assistance, and a wide scope of reactions are the advantages. Compounds5a,5b,5c,5d,5e, and6j showed 50% inhibition in antioxidant potency, whereas compounds5f,5g,5m,6h,6j, and6k showed potent activity alongside 70% inhibition of alpha-amylase and 50% inhibition of alpha-glucosidase, respectively. The results were supported by molecular docking studies of the active compounds with acarvostatin as a standard drug for antidiabetic activity.
Source: Medicinal Chemistry Research - Category: Chemistry Source Type: research