An efficient multicomponent synthesis of 1H-pyrano[2,3-d]pyrimidine-2,4(3H,5H)-dione derivatives and evaluation of their α-amylase and α-glucosidase inhibitory activity

Abstract

In this paper, we report the synthesis of novel 1 H-pyrano[2,3- d]pyrimidine-2,4(3 H,5 H)-dione derivatives 5(a–j) by a facile multicomponent reaction. The structures of all the newly synthesized compounds were characterized by different spectroscopic techniques including infrared, nuclear magnetic resonance (1H and 13C) and mass spectral analysis. All the new compounds were assessed for their in vitro α-amylase and α-glucosidase enzyme inhibitory potential. The results of the assays revealed that all compounds showed different enzyme inhibition activities. The concentration required to inhibit enzyme activity is less in the case of α-glucosidases than for α-amylases, that is, the synthesized compounds are more potent in arresting α-glucosidase enzyme activity.

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

“…Otherwise, compounds with “R = 2-OH-naphth-3-yl” displayed the most potent activity for α-amylase with IC 50 = 6.490 Mm. 98 …”

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

“…Besides, compounds with 60 "R = 2-OH-naphth-3-yl" presented the greatest effective activity for α-amylase with IC 50 = 6.490 Mm. 90 A series of chromenopyranopyrimidine-triones 124a-j was efficiently prepared, as reported by Hese et al 91 through multicomponent one-pot synthesis. Thus, the reactions of Fig.…”

“…Besides, compounds with 60 “R = 2-OH-naphth-3-yl” presented the greatest effective activity for α -amylase with IC 50 = 6.490 Mm. 90…”

Design, Synthesis, α‐Amylase/α‐Glucosidase Inhibition Assay, Induced Fit Docking Study of New Hybrid Compounds Containing 4H‐Pyrano[2,3‐d]pyrimidine, 1H‐1,2,3‐Triazole and D‐Glucose Components

“…Figure 1 below displays some examples about such bioactive compounds. Compound A exhibited inhibitory activity against both α ‐amylase and α ‐glucosidase with IC 50 value of 6.490 and 3.553 mM, respectively, in comparison to acarbose as standard inhibitor (IC 50 =0.2137 and 0.3268 mM, respectively) [11] . Pyrano[2,3‐ d ]pyrimidine B derived from curcumin also shows the inhibitory action against pancreatic α ‐amylase and yeast α ‐glucosidase with IC 50 of 9.7 μM in comparison with IC 50 =365 μM of acarbose [13] …”

“…In terms of medicinal chemistry, derivatives containing pyran [2,3-d]pyrimidine ring have numerous interesting and remarkable biological activities due to their biological property, such as antifungal, [7] antibacterial, [8] anti-inflammatory, [9] antitumor, [10] activityor against both enzymes α-glucosidase as well as α-amylase. [11] Therefore, the study on the synthesis of derivatives having pyran [2,3-d]pyrimidine ring has carried out widely and continuously. [7,9,12] Figure 1 below displays some examples about such bioactive compounds.…”