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Synthesis, DFT calculation, pharmacological evaluation, and catalytic application in the synthesis of diverse pyrano[2,3-c]pyrazole derivatives.
- Source :
-
Bioorganic chemistry [Bioorg Chem] 2021 Sep; Vol. 114, pp. 105136. Date of Electronic Publication: 2021 Jul 01. - Publication Year :
- 2021
-
Abstract
- Pyranopyrazole and its derivatives are classified to be a pharmacologically significant active scaffold for almost all modes of biological activities. In this work, An efficient, green, and facile three-component reaction for preparing pyrano[2,3-c]pyrazole derivatives via the condensation reaction of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, ethyl acetoacetate, and malononitrile in the presence of ZnO Nanoparticle. The products are produced with high yields and in shorter reaction times. It also is mild, safe, green, and environmentally friendly. The geometric parameters such as dipole moment, bond length, dihedral angles, total energy, heat of formation, atomic charges and energies at a highly accurate for prepared compounds were computed by Denisty Functional Theory along with the B3LYP functional. The newly synthesized compounds were screened for their anti-inflammatory and antioxidant activity. Some of the tested compounds displayed promising activities. The newly prepared compounds were found to be potent towards the antioxidant activity. Results indicated that compounds 11 and 12 exhibited significant (p ≥ 0.05) in vitro total antioxidant activity as 44.93 ± 0.15 and 39.60 ± 0.10 U/ML, respectively higher than standard ascorbic acid (29.40 ± 0.62).<br /> (Copyright © 2021 Elsevier Inc. All rights reserved.)
- Subjects :
- Anti-Inflammatory Agents, Non-Steroidal chemical synthesis
Anti-Inflammatory Agents, Non-Steroidal chemistry
Antioxidants chemical synthesis
Antioxidants chemistry
Arachidonate 5-Lipoxygenase metabolism
Catalysis
Cyclooxygenase Inhibitors chemical synthesis
Cyclooxygenase Inhibitors chemistry
Dose-Response Relationship, Drug
Humans
Lipoxygenase Inhibitors chemical synthesis
Lipoxygenase Inhibitors chemistry
Molecular Structure
Oxidative Stress drug effects
Prostaglandin-Endoperoxide Synthases metabolism
Pyrans chemical synthesis
Pyrans chemistry
Pyrans pharmacology
Pyrazoles chemical synthesis
Pyrazoles chemistry
Pyrazoles pharmacology
Reactive Oxygen Species metabolism
Structure-Activity Relationship
Anti-Inflammatory Agents, Non-Steroidal pharmacology
Antioxidants pharmacology
Cyclooxygenase Inhibitors pharmacology
Density Functional Theory
Lipoxygenase Inhibitors pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1090-2120
- Volume :
- 114
- Database :
- MEDLINE
- Journal :
- Bioorganic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 34328860
- Full Text :
- https://doi.org/10.1016/j.bioorg.2021.105136