Design, synthesis, and molecular docking studies of diphenylquinoxaline-6-carbohydrazide hybrids as potent α-glucosidase inhibitors

Pedrood, Keyvan; Rezaei, Zahra; Khavaninzadeh, Kimia; Larijani, Bagher; Iraji, Aida; Hosseini, Samanesadat; Mojtabavi, Somayeh; Dianatpour, Mehdi; Rastegar, Hossein; Faramarzi, Mohammad Ali; Hamedifar, Haleh; Hajimiri, Mir Hamed; Mahdavi, Mohammad

doi:10.1186/s13065-022-00848-4

Cited by 7 publications

(7 citation statements)

References 55 publications

(47 reference statements)

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“…Finally, the system was subjected to produce MD simulations for 30 ns for each protein–ligand complex. The dynamic behavior and structural changes of the systems were analyzed by the calculation of the RMSD and RMSF 24 .…”

Section: Methodsmentioning

confidence: 99%

“…1 ) as α-glucosidase inhibitors showed good potency with IC 50 values ranging between 5.31 and 53.34 μM 23 . Compound H , as a potent inhibitor with the competitive mode of inhibition, exhibited an IC 50 value of 110.6 µM in comparison with acarbose (IC 50 = 750.0 µM) 24 . Also, the potency of hydrazone linker was exhibited by participating in several interactions with the binding site of the enzyme 25 .…”

Section: Introductionmentioning

confidence: 98%

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Synthesis, in vitro α-glucosidase inhibitory activities, and molecular dynamic simulations of novel 4-hydroxyquinolinone-hydrazones as potential antidiabetic agents

Shayegan

Haghipour

Tanideh

et al. 2023

Sci Rep

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In the present study, new structural variants of 4-hydroxyquinolinone-hydrazones were designed and synthesized. The structure elucidation of the synthetic derivatives 6a–o was carried out using different spectroscopic techniques including FTIR, 1H-NMR, 13C-NMR, and elemental analysis, and their α-glucosidase inhibitory activity was also determined. The synthetic molecules 6a–o exhibited good α-glucosidase inhibition with IC50 values ranging between 93.5 ± 0.6 to 575.6 ± 0.4 µM as compared to the standard acarbose (IC50 = 752.0 ± 2.0 µM). Structure–activity relationships of this series were established which is mainly based on the position and nature of the substituent on the benzylidene ring. A kinetic study of the active compounds 6l and 6m as the most potent derivatives were also carried out to confirm the mode of inhibition. The binding interactions of the most active compounds within the active site of the enzyme were determined by molecular docking and molecular dynamic simulations.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

Synthesis, in vitro α-glucosidase inhibitory activities, and molecular dynamic simulations of novel 4-hydroxyquinolinone-hydrazones as potential antidiabetic agents

Shayegan

Haghipour

Tanideh

et al. 2023

Sci Rep

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“…The anti-α-glucosidase effects of synthesized compounds, 7a–r were screened according to the previously reported method [ 7 , 12 , 25 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis and bioactivities evaluation of quinazolin-4(3H)-one derivatives as α-glucosidase inhibitors

et al. 2022

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The development of new antidiabetes agents is necessary to obtain optimal glycemic control and overcome its complications. Different quinazolin-4(3H)-one bearing phenoxy-acetamide derivatives (7a–r) were designed and synthesized to develop α-glucosidase inhibitors. All the synthesized derivatives were evaluated against α-glucosidase in vitro and among them, compound 7b showed the highest α-glucosidase inhibition with an IC50 of 14.4 µM, which was ∼53 times stronger than that of acarbose. The inhibition kinetic studies showed that the inhibitory mechanism of compound 7b was a competitive type towards α-glucosidase. Also, molecular docking studies analyzed the interaction between the most potent derivative and α-glucosidase. Current findings indicate the new potential of quinazolin-4(3H)-ones that could be used for the development of novel agents against diabetes mellitus.

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“…The dynamic behavior and structural changes of the systems were analyzed by the calculation of the RMSD and RMSF. 34…”

Section: Molecular Dynamic Simulationmentioning

confidence: 99%

Quinazolinone-1,2,3-triazole-acetamide conjugates as potent α-glucosidase inhibitors: synthesis, enzyme inhibition, kinetic analysis, and molecular docking study

et al. 2023

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Design, synthesis, and molecular docking studies of diphenylquinoxaline-6-carbohydrazide hybrids as potent α-glucosidase inhibitors

Cited by 7 publications

References 55 publications

Synthesis, in vitro α-glucosidase inhibitory activities, and molecular dynamic simulations of novel 4-hydroxyquinolinone-hydrazones as potential antidiabetic agents

Synthesis, in vitro α-glucosidase inhibitory activities, and molecular dynamic simulations of novel 4-hydroxyquinolinone-hydrazones as potential antidiabetic agents

Synthesis and bioactivities evaluation of quinazolin-4(3H)-one derivatives as α-glucosidase inhibitors

Quinazolinone-1,2,3-triazole-acetamide conjugates as potent α-glucosidase inhibitors: synthesis, enzyme inhibition, kinetic analysis, and molecular docking study

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