Antioxidant and glycohydrolase inhibitory behavior of curcumin-based compounds: Synthesis and evaluation of anti-diabetic properties in vitro

Recent advancements in the multicomponent synthesis of heterocycles integrated with a pyrano[2,3-d]pyrimidine core

“…Recently, Mehrabi et al 96 have reported the multicomponent synthesis of bicyclic dihydropyrano-pyrimidine-dione derivatives through reactions of curcumin with aryl aldehydes, and barbituric acid in a one-pot procedure ( Scheme 15 ). The reactions were developed using catalytic borax with 10% in ethanol at reflux temperature.…”

“…The results indicated that compound 25 "Ar ¼ 4-NO 2 -C 6 H 4 " has a broad spectrum activity against E. coli species (inhibition zone diameter ¼ 11 AE 0.1 mm) relative to ampicillin (inhibition zone diameter ¼ 12 AE 0.5 mm). Recently, Mehrabi et al 96 have reported the multicomponent synthesis of bicyclic dihydropyrano-pyrimidine-dione derivatives through reactions of curcumin with aryl aldehydes, and barbituric acid in a one-pot procedure (Scheme 15). The reactions were developed using catalytic borax with 10% in ethanol at reux temperature.…”

Insights into the recent progress in the medicinal chemistry of pyranopyrimidine analogs

“…91 Ghaffarian et al 92 93 reported also the synthesis of these series of pyranopyrimidines incorporated curcumin moiety 127 using catalytic SAA-MNPs (8 mol%). In 2021, Mehrabi et al 13 and Esmaeili et al 94 synthesized these series of compounds 128 and 129 with different substituents by multicomponent one-pot synthesis using borax with 10% in ethanol at reflux temperature. All these studies investigated the antidiabetic activity of these compounds for α-amylase and α-glucosidase "carbohydrate-hydrolyzing enzymes", which are significant molecular targets for the decrease of postprandial hyperglycemia.…”

“…Thus, the compounds showed significant antioxidant characteristics as vital antidiabetic agents. 93 The antidiabetic activity of pyranopyrimidine-diones "series 128a-m" (Scheme 30) was estimated by Mehrabi et al 13 Also, compounds (series 129a′-m′) (Scheme 30) were assessed as antioxidant and glycohydrolase inhibitors as evaluated by Khodarahmi's group. 94 The results identified that compounds 129h′ Bisenieks et al 95 prepared a series of pyranopyrimidinediones 130a-g and their S-alkyl derivatives 131a-g from barbituric and thiobarbituric acids in multi-step synthetic routes (Scheme 31).…”

“…The synthesis of this category of compounds involves the synthesis of bicyclic systems at a large scale, predominately by multicomponent one-pot reactions that prefer to be applied through green methods, under solvent-free, 5 catalystfree, 6,7 or catalytic conditions, e.g., nanocatalysts, 8,9 in a basic medium, 10 polyethylene glycol 400, 11 under microwave irradiation, 12 or conventional conditions. 13 The synthesis of annulated bicyclic pyranopyrimidines was extended for the four-component synthesis, 14 under catalyst-free conditions. The mechanism of bicyclic ring constructions was proposed in general through Knoevenagel condensation, Michael addition, and intramolecular ring cyclization.…”