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Synthesis, structural characterizations, in vitro biological evaluation and computational investigations of pyrazole derivatives as potential antidiabetic and antioxidant agents.
- Source :
-
Scientific reports [Sci Rep] 2024 Jan 15; Vol. 14 (1), pp. 1312. Date of Electronic Publication: 2024 Jan 15. - Publication Year :
- 2024
-
Abstract
- In this study, a two pyrazole derivatives; 2-(5-methyl-1H-pyrazole-3-carbonyl)-N-phenylhydrazine-1-carboxamide (Pyz-1) and 4-amino-5-(5-methyl-1H-pyrazol-3-yl)-4H-1,2,4-triazole-3-thiol (Pyz-2) were synthesized and characterized by <superscript>13</superscript> C-NMR, <superscript>1</superscript> H-NMR, FT-IR, and mass spectrometry. A complete molecular structures optimization, electronic and thermodynamic properties of Pyz-1 and Pyz-2 in gas phase and aqueous solution were predicted by using hybrid B3LYP method with the 6-311++G** basis sets. Pyz-1 and Pyz-2 were evaluated in vitro for their anti-diabetic, antioxidant and xanthine oxidase inhibition activities. For anti-diabetic activity, Pyz-1 and Pyz-2 showed a potent α-glucosidase and α-amylase inhibition with IC <subscript>50</subscript> values of 75.62 ± 0.56, 95.85 ± 0.92 and 119.3 ± 0.75, 120.2 ± 0.68 µM, respectively, compared to Acarbose (IC <subscript>50(α-glucosidase)</subscript> = 72.58 ± 0.68 µM, IC <subscript>50(α-amylase)</subscript> = 115.6 ± 0.574 µM). In xanthine oxidase assay, Pyz-1 and Pyz-2 exhibited remarkable inhibitory ability with IC <subscript>50</subscript> values 24.32 ± 0.78 and 10.75 ± 0.54 µM, respectively. The result of antioxidant activities showed that the title compounds have considerable antioxidant and radical scavenger abilities. In addition, molecular docking simulation was used to determine the binding modes and energies between the title compounds and α-glucosidase and α-amylase enzymes.<br /> (© 2024. The Author(s).)
- Subjects :
- Humans
Glycoside Hydrolase Inhibitors pharmacology
Antioxidants pharmacology
Antioxidants chemistry
Molecular Docking Simulation
alpha-Glucosidases metabolism
Xanthine Oxidase
Spectroscopy, Fourier Transform Infrared
Molecular Structure
Pyrazoles pharmacology
alpha-Amylases metabolism
Structure-Activity Relationship
Hypoglycemic Agents chemistry
Diabetes Mellitus
Subjects
Details
- Language :
- English
- ISSN :
- 2045-2322
- Volume :
- 14
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- Scientific reports
- Publication Type :
- Academic Journal
- Accession number :
- 38225280
- Full Text :
- https://doi.org/10.1038/s41598-024-51290-6