Visible light induced nano copper catalyzed one pot synthesis of novel quinoline bejeweled thiobarbiturates as potential hypoglycemic agents

An efficient visible light induced one pot three component approach for the synthesis of new quinoline bejeweled thiobarbiturates via Knoevenagel condensation and N-alkylation using copper nanoparticles (CuNPs) have been reported. These copper nanoparticles due to their diverse properties, smaller size (50-100 nm), and high surface area to volume ratio exhibit promising features for the reaction response such as the shorter reaction time, simple work-up procedure, clean reaction profiles, and excellent product yields through reusability of the catalyst upto five cycles. The recovered catalyst was successfully characterized by EDAX and AFM analysis. In silico molecular docking studies were carried out to find out the effective binding affinity of the synthesized quinoline derivatives toward PPAR gamma protein. The results obtained showed that compounds 4d, 4e, and 4f possess good binding interaction toward PPAR gamma with binding energy of -7.4, -7.2 and, -7.6 k.cal/mol which was greater than standard rosiglitazone (-6.4 k.cal/mol) and comparable to that of standard pioglitazone (-7.9 k.cal/mol). In vitro alpha-amylase and alpha-glucosidase assays were performed for hypoglycemic activity evaluation. The compounds 4e and 4f at a concentration of 100 mu g/ml showed 82.13% and 83.26% inhibition toward alpha-glucosidase, 78.30% and 84.18% inhibition toward alpha-amylase which was higher than standard pioglitazone and on par to that of rosiglitazone and acarbose.

Automated summary

An efficient visible light-induced one-pot synthesis of new quinoline-bejeweled thiobarbiturates was reported using copper nanoparticles. The copper nanoparticles exhibited promising features for reaction response due to their diverse properties, smaller size, and high surface area to volume ratio. In vitro studies showed that the synthesized compounds had good binding interaction with PPAR gamma and displayed hypoglycemic activity comparable to standard medications.