Design, synthesis and biological evaluation of novel coumarin thiazole derivatives as α-glucosidase inhibitors

Wang, Guangcheng; He, Dianxiong; Li, Xin; Li, Juan; Peng, Zhiyuan

doi:10.1016/j.bioorg.2016.03.001

Cited by 46 publications

(21 citation statements)

References 33 publications

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“…Structure–activity relationship (SAR) studies proposed that electron-withdrawing substituents at phenyl of carbohydrazone improve inhibitory activity significantly. Docking analysis of compound B represented compact conformation through hydrophobic interactions of Pro240, Phe157, and Phe177 residues with coumarin ring [ 45 ]. Another series of coumarin-thiazoles were synthesized with an IC 50 value in the range of 0.12–16.20 μM as compared to standard acarbose (IC 50 = 38.25 μM).…”

Section: Resultsmentioning

confidence: 99%

One-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors

et al. 2021

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A green and efficient one-pot multi-component protocol was developed for the synthesis of some novel dihydrochromeno[4,3-b]pyrrol-3-yl derivatives through the reaction of arylglyoxals, malono derivatives, and different 4-amino coumarins in ethanol at reflux condition. In this method, all products were obtained in good to excellent yield. Next, all synthesized derivatives were evaluated for their α-glucosidase inhibitory activity. Most of the compounds displayed potent inhibitory activities with IC 50 values in the range of 48.65 ± 0.01–733.83 ± 0.10 μM compared to the standard inhibitor acarbose (IC 50 = 750.90 ± 0.14 μM). The kinetic study of compound 5e as the most potent derivative (IC 50 = 48.65 ± 0.01 μM) showed a competitive mechanism with a K i value of 42.6 µM. Moreover, docking studies revealed that dihydrochromeno[4,3-b]pyrrol-3-yl effectively interacted with important residues in the active site of α-glucosidase. Supplementary Information The online version contains supplementary material available at 10.1007/s11030-021-10337-w.

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Section: Resultsmentioning

confidence: 99%

One-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors

et al. 2021

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“…The interaction between α-glucosidase and fisetin was analyzed using a 907CRT spectrophotometer, following the method described by Jang Hoon Kim et al [22]. The fluorescence intensity of 0.5 U/mL enzyme solution mixed with different concentrations of fisetin (0-0.035 mM) was measured at 280 nm.…”

Section: Fluorescence Spectrophotometric Measurementmentioning

confidence: 99%

Inhibitory Effect of Fisetin on α-Glucosidase Activity: Kinetic and Molecular Docking Studies

et al. 2021

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The inhibition of α-glucosidase is a clinical strategy for the treatment of type 2 diabetes mellitus (T2DM), and many natural plant ingredients have been reported to be effective in alleviating hyperglycemia by inhibiting α-glucosidase. In this study, the α-glucosidase inhibitory activity of fisetin extracted from Cotinus coggygria Scop. was evaluated in vitro. The results showed that fisetin exhibited strong inhibitory activity with an IC50 value of 4.099 × 10−4 mM. Enzyme kinetic analysis revealed that fisetin is a non-competitive inhibitor of α-glucosidase, with an inhibition constant value of 0.01065 ± 0.003255 mM. Moreover, fluorescence spectrometric measurements indicated the presence of only one binding site between fisetin and α-glucosidase, with a binding constant (lgKa) of 5.896 L·mol−1. Further molecular docking studies were performed to evaluate the interaction of fisetin with several residues close to the inactive site of α-glucosidase. These studies showed that the structure of the complex was maintained by Pi-Sigma and Pi-Pi stacked interactions. These findings illustrate that fisetin extracted from Cotinus coggygria Scop. is a promising therapeutic agent for the treatment of T2DM.

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“…Efforts were highly directed toward the design and discovery of non-glycosidic based inhibitors in order to minimize the adverse effects and potentiate the inhibitory effects. [16] However, different non-glycosidic nitrogen based heterocyclic compounds including, quinazoline, [17,18] triazole, [19] imidazole, [20] thiazole, [21] and pyrazole, [22] have been recognized to be potent in vitro α-glucosidase inhibitors. Additionally, biological assessment of quinazolinone and its derivatives has gained great interest and proven promise with the discovery of potent anticancer, [23] antimicrobial, [24] anti-diabetic, [25] anticholinesterase, [26] anti-inflammatory, [27] and dihydrofolate reductase inhibitory agents.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, In‐Vivo Anti‐Diabetic Activity, In‐Vitro α‐Glucosidase Inhibitory Activity and Molecular Docking Studies of Some Quinazolinone Derivatives

et al. 2022

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A new series of quinazolinone bearing acetamide derivatives were designed and synthesized. The designed compounds were tested for their in vivo anti‐hyperglycemic effects against STZ‐induced hyperglycemic rats. Compound 10 a displayed the strongest hypoglycemic effect with blood glucose level reduction of 43.75 %. Besides, congeners 10 e, 10 i, 10 j, and 11 c strongly reduced the glucose level with percent reduction of 33.08, 30.00, 35.00, and 32.83 %, respectively. The most active members were then evaluated for their ability to inhibit Saccharomyces cerevisiae α‐glucosidase using BioVision α‐Glucosidase Inhibitor Screening Kit. Compounds 10 a and 11 c possessed potent α‐glucosidase inhibitory activity with IC50 values of 649 and 715 μM, respectively. Molecular docking study against the α‐glucosidase homology model was performed to understand the molecular interactions between the molecule and enzyme.

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Design, synthesis and biological evaluation of novel coumarin thiazole derivatives as α-glucosidase inhibitors

Cited by 46 publications

References 33 publications

One-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors

One-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors

Inhibitory Effect of Fisetin on α-Glucosidase Activity: Kinetic and Molecular Docking Studies

Design, Synthesis, In‐Vivo Anti‐Diabetic Activity, In‐Vitro α‐Glucosidase Inhibitory Activity and Molecular Docking Studies of Some Quinazolinone Derivatives

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