Novel tetrahydrobenzo[b]thiophen-2-yl)urea derivatives as novel α-glucosidase inhibitors: Synthesis, kinetics study, molecular docking, and in vivo anti-hyperglycemic evaluation

Xie, Hui; Zhang, Juan; Li, Yue; Zhang, Jinhe; Liu, Shan-Kui; Zhang, Jie; Zheng, Han; Hao, Guizhou; Zhu, Kongkai; Jiang, Cheng‐Shi

doi:10.1016/j.bioorg.2021.105236

Cited by 27 publications

(18 citation statements)

References 47 publications

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“…The α -glucosidase inhibitory assay was performed as previously described by Xie et al 42 , with some modifications. In brief, inhibitors were dissolved in 0.5% DMSO, α -glucosidase (45 µL, 0.3 U/mL) were mixed with test samples of different concentrations in a 96-well plate.…”

Section: Methodsmentioning

confidence: 99%

Oligomeric Proanthocyanidin Complex from Avocado Seed as A Promising α-glucosidase Inhibitor: Characteristics and Mechanisms

et al. 2022

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Although considered as an abundant source of agricultural by-products, avocado (Persea americana Mill.) seed, with several biological activities and bioactive components, might become a promising resource for phytopharmaceutical development. In this study, through bioassay-guided isolation of the main α-glucosidase inhibitors in avocado seed, we discovered the major α-glucosidase inhibitor to be avocado seed oligomeric proanthocyanidin complex (ASOPC). Thiolysis and UPLC-DAD-HRESIMS showed the presence of A- and B-type procyanidins, and B-type propelargonidin with (epi)afzelechin as extension unit. Mean degree of polymerization (mDP) of ASOPC was calculated as 7.3±1. Furthermore, ASOPC appeared to be a strong, reversible, competitive inhibitor of α-glucosidase, with IC50 value of 0.1 µg/mL, which was significantly lower than Acarbose (IC50 = 75.6 µg/mL), indicated that ASOPC is a potential natural α-glucosidase inhibitor. These findings would contribute to the direction of utilizing avocado seed bioactive components with the possibility to be used as natural anti-diabetic agents.

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Section: Methodsmentioning

confidence: 99%

Oligomeric Proanthocyanidin Complex from Avocado Seed as A Promising α-glucosidase Inhibitor: Characteristics and Mechanisms

et al. 2022

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“…Urea derivatives are well known anti-diabetic agents via targeting α -glucosidase enzyme. Several inhibitors have previously been discovered for this class demonstrating their potential for use in drug discovery 14 – 17 . Apart this phenyl urea comprising compounds and urea derivatives have been already reported for their anti-α-glucosidase inhibitory capability 18 , 19 (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new diphenyl urea-clubbed imine analogs and its Implications in diabetic management through in vitro and in silico approaches

Pasha

Khan

Ullah

et al. 2023

Sci Rep

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Type II diabetes mellitus (T2DM) is a global health issue with high rate of prevalence. The inhibition of α-glucosidase enzyme has prime importance in the management of T2DM. This study was established to synthesize Schiff bases of 1,3-dipheny urea (3a–y) and to investigate their in vitro anti-diabetic capability via inhibiting α-glucosidase, a key player in the catabolism of carbohydrates. The structures of all compounds were confirmed through various techniques including, Fourier-transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR) and mass-spectrometry (MS) methods. Interestingly all these compounds displayed potent inhibition IC50 values in range of 2.14–115 µM as compared to acarbose used as control. Additionally, all the compounds were docked at the active site of α-glucosidase to predict their mode of binding. The docking results indicates that Glu277 and Asn350 play important role in the stabilization of these compounds in the active site of enzyme. These molecules showed excellent predicted pharmacokinetics, physicochemical and drug-likeness profile. The anti-diabetic potential of these molecules signifies their medical importance and provide insights into prospective therapeutic options for the treatment of T2DM.

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“…However, undesired effects of these drugs, such as flatulence, diarrhea and stomach ache, imposed a great limitation on their clinical application [12] . Therefore, the efforts in the development of new effective α‐glucosidase inhibitors from worldwide and our groups have been continuously made [13–16] …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Substituted Pyrazole‐Fused Oleanolic Acid Derivatives as Novel Selective α‐Glucosidase Inhibitors

Gao

Liu

et al. 2023

Chemistry & Biodiversity

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A series of novel substituted pyrazole-fused oleanolic acid derivative were synthesized and evaluated as selective α-glucosidase inhibitors. Among these analogs, compounds 4a-4f exhibited more potent inhibitory activities compared with their methyl ester derivatives, and standard drugs acarbose and miglitol as well. Besides, all these analogs exhibited good selectivity towards α-glucosidase over α-amylase. Analog 4d showed potent inhibitory activity against α-glucosidase (IC 50 = 2.64 � 0.13 μM), and greater selectivity towards αglucosidase than α-amylase by ~33-fold. Inhibition kinetics showed that compound 4d was a non-competitive α-glucosidase inhibitor, which was consistent with the result of its simulation molecular docking. Moreover, the in vitro cytotoxicity of compounds 4a-4f towards hepatic LO2 and HepG2 cells was tested.

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Novel tetrahydrobenzo[b]thiophen-2-yl)urea derivatives as novel α-glucosidase inhibitors: Synthesis, kinetics study, molecular docking, and in vivo anti-hyperglycemic evaluation

Cited by 27 publications

References 47 publications

Oligomeric Proanthocyanidin Complex from Avocado Seed as A Promising α-glucosidase Inhibitor: Characteristics and Mechanisms

Oligomeric Proanthocyanidin Complex from Avocado Seed as A Promising α-glucosidase Inhibitor: Characteristics and Mechanisms

Synthesis of new diphenyl urea-clubbed imine analogs and its Implications in diabetic management through in vitro and in silico approaches

Synthesis and Biological Evaluation of Substituted Pyrazole‐Fused Oleanolic Acid Derivatives as Novel Selective α‐Glucosidase Inhibitors

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