Synthesis, in vitro Α-Glucosidase, and acetylcholinesterase inhibitory activities of novel Indol-Fused Pyrano[2,3-D]Pyrimidine compounds.

[Display omitted] • New indol-fused pyrano-[2,3- d ]pyrimidines 11a-l were designed and synthesized. • The plausible mechanism for formation of compounds 11a-l was described. • Their α-glucosidase and acetylcholinesterase inhibitory activities were evaluated. • α-Glucosidase inhibitors 11d , e were around 93-fold more potent than acarbose. • Product 11 k exhibited good acetylcholinesterase inhibitory activity. In this study, new indol-fused pyrano[2,3- d ]pyrimidines were designed and synthesized. These products were obtained in moderate to good yields and their structures were assigned by NMR, MS, and IR analysis. Afterwards, the biological important of the products was highlighted by evaluating in vitro for α-glucosidase inhibitory activity as well as acetylcholinesterase (AChE) inhibitory activity. Eleven products revealed substantial inhibitory activity against α-glucosidase enzyme, among which, two most potent products 11d,e were approximately 93-fold more potent than acarbose as a standard antidiabetic drug. Besides that, product 11 k exhibited good AChE inhibition. The substituents on the 5-phenyl ring, attached to the pyran ring, played a critical role in inhibitory activities. The biological potencies have provided an opportunity to further investigations of indol-fused pyrano[2,3- d ]pyrimidines as potential anti-diabetic agents. [ABSTRACT FROM AUTHOR]