Synthesis, crystal structure, DFT, α-glucosidase and α-amylase inhibition and molecular docking studies of (E)-N'-(4-chlorobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide

Karrouchi, Khalid; Fettach, Saad; Anouar, El Hassane; Tüzün, Burak; Radi, Smaail; Alharthi, Abdulrahman I.; Ghabbour, Hazem A.; Mabkhot, Yahia N.; Faouzi, My El Abbes; Ansar, Mʼhammed; Garcia, Yann

doi:10.1016/j.molstruc.2021.131067

Cited by 46 publications

(16 citation statements)

References 34 publications

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“…With these calculations, the numerical value of the parameters of the compounds is taken into account in order to predict the activities of the compounds. [ 15,16 ]…”

Section: Resultsmentioning

confidence: 99%

“…In recent studies, molecular activities are reinforced by comparing theoretical calculations with experimental results. [ 15,16 ] The results obtained will guide many future studies. It is possible to compare the activities of molecules with quantum chemical calculations of molecules.…”

Section: Introductionmentioning

confidence: 81%

“…With these calculations, the numerical value of the parameters of the compounds is taken into account in order to predict the activities of the compounds. [15,16] The two parameters checked to compare the activities of compounds are the highest-occupied molecular orbital (HOMO) and the lowest-unoccupied molecular orbital (LUMO) of the compounds. These two parameters are used to explain the chemical activities of compounds.…”

Section: In Silico Calculationsmentioning

confidence: 99%

“…[15] On the other hand, electron- poor blue regions are regions with a high probability of accepting electrons and interacting. [16] Therefore, this figure in which electrostatic potentials are shown is very important for the activity of the compound. Quantum chemical parameters alone are not sufficient to compare the activities of compounds.…”

Section: In Silico Calculationsmentioning

confidence: 99%

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Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Yalazan

Tüzün

Akkaya

et al. 2022

Applied Organom Chemis

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Quinoline-fused Zn II (ZnPc p /ZnPc np ) and Mg II (MgPc p /MgPc np ) phthalocyanines with four 4-methylquinolin-2-ol (1) at non-peripheral or peripheral positions of the phthalocyanine core have been synthesized via cyclotetramerization of phthalonitrile derivatives (CN p /CN np ) in the presence of zinc (II) and magnesium (II) metal ions in this study. After synthesis and characterization processes, anti-cholinesterase, anti-α-glucosidase, DNA nuclease, antioxidant activities, and in silico calculations of both peripheral and non-peripheral Zn II and Mg II phthalocyanines were investigated. The inhibitory effects of metallated phthalocyanines on acetylcholinesterase, butyrylcholinesterase, and α-glucosidase enzymes were tested by spectrophotometric method. Theoretical methods are used to compare both the chemical and biological activities of the studied phthalonitrile derivatives and metallated phthalocyanine compounds.

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“…With these calculations, the numerical value of the parameters of the compounds is taken into account in order to predict the activities of the compounds. [ 15,16 ]…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 81%

Section: In Silico Calculationsmentioning

confidence: 99%

Section: In Silico Calculationsmentioning

confidence: 99%

See 2 more Smart Citations

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Yalazan

Tüzün

Akkaya

et al. 2022

Applied Organom Chemis

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“…The current study intended to evaluate the efficacy of a set of pyrazole derivatives synthesized in-house [ 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 ] (63 structures that are displayed in Supplementary Information ) against six important cancer targets: CRMP2, C-RAF, CYP17, c-KIT, VEGFR, and HDAC9.…”

Section: Introductionmentioning

confidence: 99%

In Silico Identification of Promising New Pyrazole Derivative-Based Small Molecules for Modulating CRMP2, C-RAF, CYP17, VEGFR, C-KIT, and HDAC—Application towards Cancer Therapeutics

Bennani

Karrouchi

Doudach

et al. 2022

CIMB

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Despite continual efforts being made with multiple clinical studies and deploying cutting-edge diagnostic tools and technologies, the discovery of new cancer therapies remains of severe worldwide concern. Multiple drug resistance has also emerged in several cancer cell types, leaving them unresponsive to the many cancer treatments. Such a condition always prompts the development of next-generation cancer therapies that have a better chance of inhibiting selective target macromolecules with less toxicity. Therefore, in the present study, extensive computational approaches were implemented combining molecular docking and dynamic simulation studies for identifying potent pyrazole-based inhibitors or modulators for CRMP2, C-RAF, CYP17, c-KIT, VEGFR, and HDAC proteins. All of these proteins are in some way linked to the development of numerous forms of cancer, including breast, liver, prostate, kidney, and stomach cancers. In order to identify potential compounds, 63 in-house synthesized pyrazole-derivative compounds were docked with each selected protein. In addition, single or multiple standard drug compounds of each protein were also considered for docking analyses and their results used for comparison purposes. Afterward, based on the binding affinity and interaction profile of pyrazole compounds of each protein, potentially strong compounds were filtered out and further subjected to 1000 ns MD simulation analyses. Analyzing parameters such as RMSD, RMSF, RoG and protein–ligand contact maps were derived from trajectories of simulated protein–ligand complexes. All these parameters turned out to be satisfactory and within the acceptable range to support the structural integrity and interaction stability of the protein–ligand complexes in dynamic state. Comprehensive computational analyses suggested that a few identified pyrazole compounds, such as M33, M36, M72, and M76, could be potential inhibitors or modulators for HDAC, C-RAF, CYP72 and VEGFR proteins, respectively. Another pyrazole compound, M74, turned out to be a very promising dual inhibitor/modulator for CRMP2 and c-KIT proteins. However, more extensive study may be required for further optimization of the selected chemical framework of pyrazole derivatives to yield improved inhibitory activity against each studied protein receptor.

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Pyrazole scaffold‐based derivatives: A glimpse of α‐glucosidase inhibitory activity, SAR, and route of synthesis

Firdaus

Siddiqui

Alam

et al. 2023

Archiv der Pharmazie

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The α-glucosidase is a validated target to develop drugs for treating type 2 diabetes mellitus. The existing α-glucosidase inhibitors have certain shortcomings related to side effects and route of synthesis. Accordingly, it is inevitable to develop new chemical templates as α-glucosidase inhibitors. Pyrazole derivatives have a special place in medicinal chemistry because of various biological activities. Recently, pyrazole-based heterocyclic compounds have emerged as a promising scaffold to develop α-glucosidase inhibitors. This study focuses on the recently reported pyrazole-based α-glucosidase inhibitors, including their biological activity (in vivo, in vitro, and in silico), structure-activity relationship, and ways of synthesis. The literature revealed the development of several promising pyrazole-based α-glucosidase inhibitors and new synthetic routes for their preparation. The encouraging α-glucosidase inhibitory results of the pyrazole-based heterocyclic compounds make them an attractive target for further research. The authors also foresee the arrival of the pyrazole-based α-glucosidase inhibitors in clinical practice.

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Synthesis, crystal structure, DFT, α-glucosidase and α-amylase inhibition and molecular docking studies of (E)-N'-(4-chlorobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide

Cited by 46 publications

References 34 publications

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

In Silico Identification of Promising New Pyrazole Derivative-Based Small Molecules for Modulating CRMP2, C-RAF, CYP17, VEGFR, C-KIT, and HDAC—Application towards Cancer Therapeutics

Pyrazole scaffold‐based derivatives: A glimpse of α‐glucosidase inhibitory activity, SAR, and route of synthesis

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Synthesis, crystal structure, DFT, α-glucosidase and α-amylase inhibition and molecular docking studies of (E)-N'-(4-chlorobenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide

Cited by 46 publications

References 34 publications

Quinoline‐fused both non‐peripheral and peripheral ZnIIand MgIIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Quinoline‐fused both non‐peripheral and peripheral ZnIIand MgIIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

In Silico Identification of Promising New Pyrazole Derivative-Based Small Molecules for Modulating CRMP2, C-RAF, CYP17, VEGFR, C-KIT, and HDAC—Application towards Cancer Therapeutics

Pyrazole scaffold‐based derivatives: A glimpse of α‐glucosidase inhibitory activity, SAR, and route of synthesis

Contact Info

Product

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Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies