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Synthesis, molecular properties, anti-inflammatory and anticancer activities of novel 3-hydroxyflavone derivatives.

Abstract
A new series of 3-hydroxyflavones (1-46) were synthesized according to the Claisen-Schmidt followed by Algar-Flynn-Oyamada reactions (AFO) in one step. The synthesized flavonoids were characterized by 1H NMR, 13C NMR and DCI-HRMS. All the synthesized compounds were tested in vitro for their 15-lipoxygenase inhibitory and cytotoxic activity against the human cell lines HCT-116 (Human colon carcinoma), IGROV-1 and OVCAR-3 (human ovarian carcinoma). It has been found that the derivatives 25, 37 and 45 were the most actives against HCT-116 (IC50 = 8.0, 9.0 and 9.0 μM, respectively) and against IGROV-1 (IC50 = 2.4, 5.0 and 6.0 μM, respectively). The derivatives 14 and 21 exhibited the higher anti-inflammatory activity at 100 μM with PI values of 76.50 and 72.70%, respectively. Molecule description was performed with DFT calculations, the drug likeness and bioactivity scores. The results exhibted that some compounds are in linear correlation with Lipinski's rule of five showing good drug likeness and bioactivity score for drug targets.
AuthorsMansour Znati, Claire Bordes, Valérian Forquet, Pierre Lantéri, Hichem Ben Jannet, Jalloul Bouajila
JournalBioorganic chemistry (Bioorg Chem) Vol. 89 Pg. 103009 (08 2019) ISSN: 1090-2120 [Electronic] United States
PMID31158579 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
CopyrightCopyright © 2019 Elsevier Inc. All rights reserved.
Chemical References
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antineoplastic Agents
  • Flavonoids
  • Lipoxygenase Inhibitors
  • Arachidonate 15-Lipoxygenase
  • 3-hydroxyflavone
Topics
  • Anti-Inflammatory Agents, Non-Steroidal (chemical synthesis, chemistry, pharmacology)
  • Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
  • Arachidonate 15-Lipoxygenase (metabolism)
  • Cell Line, Tumor
  • Cell Proliferation (drug effects)
  • Density Functional Theory
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Flavonoids (chemical synthesis, chemistry, pharmacology)
  • HCT116 Cells
  • Humans
  • Lipoxygenase Inhibitors (chemical synthesis, chemistry, pharmacology)
  • Molecular Structure
  • Structure-Activity Relationship

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