Synthesis, molecular properties, anti-inflammatory and anticancer activities of novel 3-hydroxyflavone derivatives.
Bioorg Chem
; 89: 103009, 2019 08.
Article
em En
| MEDLINE
| ID: mdl-31158579
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 (IC50â¯=â¯8.0, 9.0 and 9.0⯵M, respectively) and against IGROV-1 (IC50â¯=â¯2.4, 5.0 and 6.0⯵M, respectively). The derivatives 14 and 21 exhibited the higher anti-inflammatory activity at 100⯵M 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.
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Texto completo:
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Base de dados:
MEDLINE
Assunto principal:
Flavonoides
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Araquidonato 15-Lipoxigenase
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Anti-Inflamatórios não Esteroides
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Inibidores de Lipoxigenase
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Antineoplásicos
Limite:
Humans
Idioma:
En
Revista:
Bioorg Chem
Ano de publicação:
2019
Tipo de documento:
Article