- An Efficient One-Pot Synthesis and Anticancer Activity of 4'-Substituted Flavonoids
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A number of 4'-substituted (R = H, Me, Cl, F) flavone derivatives is synthesized from 2-hydroxyacetophenones using the modified Baker–Venkataraman reaction. Compound [3-(4-fluorobenzoyl)-5- hydroxy-4'-fluoroflavone] was synthesized for the first time with the yield of 12%. Antiproliferative assays indicate that the synthesized flavones with F substituent at the 4' position demonstrate higher activity than the other flavone derivatives, particularly against HeLa and MCF-7 with the IC50 9.5 and 2.7 μM, respectively.
- Wang,Liu,Zhang
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p. 1036 - 1041
(2018/07/06)
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- An efficient one-pot synthesis of flavones
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Flavones were prepared using a one-pot procedure starting from the corresponding 2′-hydroxyacetophenones. The latter were treated with 3 equiv of aroyl chloride in wet K2CO3/acetone (1% w/w water) to afford a good yield of flavone and a smaller amount of 3-aroylflavone. Evidence was obtained that the reaction proceeds via a triketone intermediate. When the reactants were heated in 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and pyridine, the 3-aroylflavone was obtained exclusively. Use of a stoichiometric amount of aroyl chloride afforded only the corresponding flavone.
- Chee, Chin Fei,Buckle, Michael J.C.,Rahman, Noorsaadah Abd.
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supporting information; experimental part
p. 3120 - 3123
(2011/06/26)
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- Baker-venkataraman rearrangement under microwave irradiation: A new strategy for the synthesis of 3-aroyl-5-hydroxyflavones
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Microwave irradiation selectively induces the Baker-Venkataraman rearrangement of 2′,6′-diaroyloxyacetophenones to give 3-aroyl-5-hydroxyflavones, in a very short reaction time. Under classical heating conditions these reactions afforded 5-hydroxyflavones
- Pinto, Diana C. G. A.,Silva, Artur M. S.,Cavaleiro, José A. S.
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p. 1897 - 1900
(2008/03/13)
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- 3-Aroyl-5-hydroxyflavones: Synthesis and transformation into aroylpyrazoles
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Treatment of 3-aroyl-5-benzyloxyflavones 4a-e with hydrazine afforded 3,5-diaryl-4-(2-benzyloxy-6-hydroxybenzoyl)pyrazoles 5a-e, together with 4-aroyl-5-aryl-3-(2-benzyloxy-6- hydroxyphenyl)pyrazoles 6a-e as minor products. The structures of all new compounds have been established by extensive NMR studies and the reaction mechanisms are discussed. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
- Pinto, Diana C. G. A.,Silva, Artur M. S.,Almeida, Lucia M. P. M.,Cavaleiro, Jose A. S.,Elguero, Jose
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p. 3807 - 3815
(2007/10/03)
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- 3-Aroyl-5-hydroxyflavones: Synthesis and mechanistic studies by mass spectrometry
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The synthesis and mass spectra of three 3-aroyl-5-hydroxflavones are reported. The interpretation of the mechanistic pathways for the fragmentation of the metastable molecular ions of these compounds was achieved through the analysis of their mass-analysed ion kinetic energy (MIKE) spectra and of the B2/E spectra of a few fragment ions. Labelling of the hydroxyl proton with deuterium and the analysis of the MIKE spectra of a model compound with chlorine atoms in the 2',6'- and 2',6'-positions led to a mechanism for the losses of OH. and HCO. which involves hydrogen migration from the 2'- or 6'-position to the 6-carbonyl oxygen atom. A mechanism for the loss of a neutral molecule of anisole from the molecular ion of the 3-aroyl-5-hydroxyflavone with a methoxyl group in the 4'- and 4'-positions is also suggested. For the flavones with hydrogen or chlorine substituents at these positions, loss of a phenyl (or chlorophenyl) radical occurs instead.
- Cardoso, Ana M.,Silva, Artur M. S.,Barros, Cristina M. F.,Almeida, Lucia M. P. M.,Ferrer-Correia,Cavaleiro, Jose A. S.
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p. 930 - 939
(2007/10/03)
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