Synthesis, in Silico Physicochemical Properties and Biological Activities of Some Pyrazoline Derivatives

Pj, Jainey; K, Ishwar Bhat

doi:10.22159/ajpcr.2017.v10i4.17093

Cited by 3 publications

(1 citation statement)

References 7 publications

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“…An extension of previous works on pyrazole scaffolds [21,22] and in silico studies [23,24], we have performed an analysis to screen the inhibitory potency of synthesized pyrazole fused derivatives on various targets EGFR, ALK, VEGFR and TNKS by employing molecular docking and pharmacophore modelling techniques.…”

Section: Introductionmentioning

confidence: 99%

Structure-Based Multitargeted Molecular Docking Analysis of Pyrazole-Condensed Heterocyclics Against Lung Cancer

et al. 2021

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Objective: The significant drawbacks of chemotherapy are that it destroys healthy cells, resulting in adverse effects. Hence, there is a need to adopt new techniques to develop cancer-specific chemicals that target the molecular pathways in a non-toxic fashion. This study aims to screen pyrazole-condensed heterocyclics for their anticancer activities and analyse their enzyme inhibitory potentials EGFR, ALK, VEGFR and TNKS receptors. Methods: The structures of the compounds were confirmed by IR, NMR and Mass spectral studies. The in silico techniques applied in this study were molecular docking and pharmacophore modeling to analyse the protein-ligand interactions, as they have a significant role in drug discovery. Drug-likeness properties were assessed by the Lipinski rule of five and ADMET properties. Anticancer activity was performed by in vitro MTT assay on lung cancer cell lines. Results: The results confirm that all the synthesised pyrazole derivatives interacted well with the selected targets showing docking scores above-5 kcal/mol. Pyrazole 2e interacted well with all the four lung cancer targets with its stable binding mode and was found to be potent as per the in vitro reports, followed by compounds 3d and 2d. Pharmacophore modeling exposed the responsible features responsible for the anticancer action. ADMET properties reported that all the compounds were found to have properties within the standard limit. The activity spectra of the pyrazoles predicted that pyrazolopyridines (2a-2e) are more effective against specific receptors such as EGFR, ALK and Tankyrase. Conclusion: Thus, this study suggests that the synthesised pyrazole derivatives can be further investigated to validate their enzyme inhibitory potentials by in vivo studies.

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Section: Introductionmentioning

confidence: 99%

Structure-Based Multitargeted Molecular Docking Analysis of Pyrazole-Condensed Heterocyclics Against Lung Cancer

et al. 2021

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Cyclocondensation of 2‐Hydroxyimino‐1‐(naphthalen‐1‐yl)butane‐1,3‐dione with Alkyl Hydrazines Leading to Substituted 4‐Nitrosopyrazoles

et al. 2020

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Cyclocondensation of 2‐(hydroxyimino)‐1‐(naphthalen‐1‐yl)butane‐1,3‐dione with alkyl hydrazines leading to new 1‐alkyl‐3(5)‐methyl‐5(3)‐(naphthalene‐1‐yl)‐4‐nitrosopyrazoles is described. 8 previously unknown N‐alkyl‐4‐nitrosopyrazoles with a 1‐naphthalene substituent at the 3 or 5 position of the pyrazole ring were obtained as a result. It was found that yields of naphthyl‐substituted pyrazoles with N‐alkyl groups near the naphthalene substituent were significantly lower than for 3‐(naphthalen‐1‐yl)‐substituted pyrazoles. Particular yields of pairwise formed isomeric nitrosopyrazoles were associated with the different electrophilicity of the two carbonyl groups of the initial diketone. Using quantum chemical calculations by the DFT method B3LYP−D3/6‐311G(d,p), the potential energies of the various conformers were estimated to draw a conclusion about the preferred attack of alkyl hydrazine on the carbonyl group, associated with the naphthalene ring. 1H NMR and 2D 1H‐13C HSQC spectra of the compounds confirmed this direction of the reaction. The crystal structures of the synthesized compounds were established by X‐ray powder diffraction technique. Crystal structure data were in agreement with quantum chemical calculations.

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Tyrosinase and Peroxiredoxin Inhibitory Action of Ethanolic Extracts of Memecylon malabaricum Leaves

P. James,

Crasta,

Shetty

et al. 2024

RJPT

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The study aimed to determine the tyrosinase and peroxiredoxin inhibitory action of ethanolic extracts of Memecylon malabaricum leaves. The phytoconstituents present in Memecylon malabaricum were analysed for their inhibitory activity against the tyrosinase and peroxiredoxin enzymes by molecular docking, and their molecular interactions were confirmed. The Qikprop module checked their pharmacokinetic profiles. The ethanolic extracts were prepared, and they were analysed for antityrosinase and antioxidant activity by in vitro methods. All the fourteen phytoconstituents obtained from Memecylon malabaricum were docked with two proteins, tyrosinase (5I38) and peroxiredoxin (1HD2), and MM1 was the well-interacted compound. The ethanolic extract was evaluated for tyrosinase inhibitory activity and antioxidant activity using the DPPH radical scavenging method and was compared with the standard ascorbic acid. It was concluded that the ethanolic extract of Memecylon malabaricum was active, and further pharmacological studies were needed to confirm their potency.

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Synthesis, in Silico Physicochemical Properties and Biological Activities of Some Pyrazoline Derivatives

Cited by 3 publications

References 7 publications

Structure-Based Multitargeted Molecular Docking Analysis of Pyrazole-Condensed Heterocyclics Against Lung Cancer

Structure-Based Multitargeted Molecular Docking Analysis of Pyrazole-Condensed Heterocyclics Against Lung Cancer

Cyclocondensation of 2‐Hydroxyimino‐1‐(naphthalen‐1‐yl)butane‐1,3‐dione with Alkyl Hydrazines Leading to Substituted 4‐Nitrosopyrazoles

Tyrosinase and Peroxiredoxin Inhibitory Action of Ethanolic Extracts of Memecylon malabaricum Leaves

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