Hetarylcoumarins: Synthesis and biological evaluation as potent α -glucosidase inhibitors

Chaudhry, Faryal; Choudhry, Shahnaz; Huma, Rahila; Ashraf, Muhammad; al‐Rashida, Mariya; Munir, Rubina; Sohail, Ramsha; Jahan, Bakhat; Munawar, Munawar Ali; Khan, Misbahul Ain

doi:10.1016/j.bioorg.2017.05.009

Cited by 38 publications

(20 citation statements)

References 42 publications

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“…anticancer, non steroidal inflammatory drugs, antidepressant, antiviral, antioxidant, etc . α‐Glucosidase inhibitory potential of pyrazole containing molecules has been exhaustively investigated by researchers and it was reported that several compounds of this category were many folds potent than the standard drug acarbose (compound 5–8 , Figure b) . Pyrazole nucleus has also been an essential part of an antidiabetic drug (Teneligliptin) marketed in Japan…”

Section: Introductionsupporting

confidence: 90%

Hybrids of Isatin‐Pyrazole as Potential α‐Glucosidase Inhibitors: Synthesis, Biological Evaluations and Molecular Docking Studies

2019

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α‐Glucosidase inhibition has been considered as an effective strategy for controlling the post‐prandial hyperglycemia in diabetic patients. A series of novel isatin‐pyrazole hybrids has been rationally designed, synthesized and characterized by different spectroscopic techniques. All of the synthesized compounds were evaluated for their α‐glucosidase inhibitory potential using in vitro enzymatic assay. The tested compounds have exhibited potent α‐glucosidase inhibition with IC50 values ranging from 3.26±0.25 to 32.33±1.08 μM. Compound V7, having 3‐nitro phenyl ring appended at pyrazole nucleus, has emerged as the most potent inhibitor among the series with an IC50 value of 3.26±0.25 μM, which was approximately 146 fold more potent than the clinically used drug acarbose (IC50=478.07±1.53 μM). Molecular docking studies were carried out to investigate the binding interactions of most active compounds with the active site of the enzyme. Further, in silico predictive pharmacokinetic parameters (ADME) and drug‐like properties of the compounds were within the acceptable ranges. In vivo biological evaluations further supplemented the in vitro results.

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Section: Introductionsupporting

confidence: 90%

Hybrids of Isatin‐Pyrazole as Potential α‐Glucosidase Inhibitors: Synthesis, Biological Evaluations and Molecular Docking Studies

2019

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“…α‐Glucosidase (EC 3.2.1.20) which is a carbohydrate‐hydrolase to release glucose specifically hydrolyses the 1,4‐α‐glucopyranosidic bond . α‐Glucosidase, a critical enzyme for the digestion of carbohydrates, catalyzes the cleavage of absorbable monosaccharides, beginning from disaccharides and oligosaccharides . The functions of α‐glucosidase for mammals contain intestinal digestion of dietary carbohydrates, glycogen degradation, and glycoprotein folding and maturation .…”

Section: Introductionmentioning

confidence: 99%

A new dinuclear copper (II) complex of 2,5–Furandicarboxyclic acid with 4(5)‐Methylimidazole as a high potential α‐glucosidase inhibitor: Synthesis, Crystal structure, Cytotoxicity study, and TD/DFT calculations

Avcı

Altürk

Sönmez

et al. 2019

Applied Organom Chemis

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A new dinuclear copper (II) complex of 2,5–furandicarboxyclic acid with 4(5)‐methylimidazole, [Cu (FDCA)((4(5)MeI)2]2·2H2O, was synthesized, and its structure characterized by XRD, FT–IR and UV–Vis spectroscopic techniques. The α‐glucosidase inhibition and cytotoxicity study of the synthesized Cu (II) complex were determined by IC50 values. The optimized geometry and vibrational harmonic frequencies for the Cu (II) complex were obtained by using Density Functional Theory (DFT) of HSEh1PBE/6–311++G(d,p)/LanL2DZ level. TD‐DFT/HSEh1PBE/6–311++G(d,p)/LanL2DZ level with CPCM model was applied to examine the electronic spectral properties and major contributions were determined via Swizard program. To investigate linear and nonlinear optical behavior of the synthesized Cu (II) complex, the α, Δα and χ(1)/β, γ and χ(3) parameters called linear/nonlinear optical parameters in gas phase and ethanol solvent were computed at the same level and basis set. Furthermore, molecular electrostatic potential (MEP) surface was determined by using the same level. The docking study of the Cu (II) complex to the binding site of the target protein (the template structure S. cerevisiae isomaltase) is fulfilled. Natural bond orbital (NBO) analysis was used to investigate the hyperconjugative interactions, inter‐ and intra‐molecular bonding and to determine coordination around Cu (II) ion. Finally, present work is the first remarkable scientific report of mixed‐ligand (H2FDCA and 4(5)MeI) Cu (II) complex as novel drug candidate for DM II. It is also determined that microscopic third−NLO parameters for the Cu (II) complex is remarkable.

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“…As a result, postprandial blood glucose level comes under control and helps to cure T2DM. Some α‐glycosidase inhibiting medicines such as acarbose, miglitol, and voglibose are clinically recommended …”

Section: Introductionmentioning

confidence: 99%

“…Both enzyme inhibitors can reduce the level of glucose absorption and disturb the absorption of glucose in the digestive device, lengthening the carbohydrate digestion period . As an outcome, the postprandial blood glucose amount is reduced .…”

Section: Introductionmentioning

confidence: 99%

Antidiabetic potential: in vitro inhibition effects of some natural phenolic compounds on α‐glycosidase and α‐amylase enzymes

Taslimi

Gülçın

2017

J Biochem & Molecular Tox

121

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α-Glycosidase is a catalytic enzyme and it destroys the complex carbohydrates into simple absorbable sugar units. The natural phenolic compounds were tested for their antidiabetic properties as α-glycosidase and α-amylase inhibitors. The phenolic compounds investigated in this study have been used as antidiabetic common medicines. This paper aimed to consider their capability to inhibit α-amylase and α-glycosidase, two significant enzymes defined in serum glucose adjustment. These examination recorded impressive inhibition profiles with IC values in the range of 137.36-737.23 nM against α-amylase and 29.01-157.96 nM against α-glycosidase.

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Hetarylcoumarins: Synthesis and biological evaluation as potent α -glucosidase inhibitors

Cited by 38 publications

References 42 publications

Hybrids of Isatin‐Pyrazole as Potential α‐Glucosidase Inhibitors: Synthesis, Biological Evaluations and Molecular Docking Studies

Hybrids of Isatin‐Pyrazole as Potential α‐Glucosidase Inhibitors: Synthesis, Biological Evaluations and Molecular Docking Studies

A new dinuclear copper (II) complex of 2,5–Furandicarboxyclic acid with 4(5)‐Methylimidazole as a high potential α‐glucosidase inhibitor: Synthesis, Crystal structure, Cytotoxicity study, and TD/DFT calculations

Antidiabetic potential: in vitro inhibition effects of some natural phenolic compounds on α‐glycosidase and α‐amylase enzymes

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