38216-58-9Relevant academic research and scientific papers
An efficient synthesis of aurone derivatives by the tributylphosphine-catalyzed regioselective cyclization of o-alkynoylphenols
Saito, Koya,Yoshida, Masahito,Doi, Takayuki
supporting information, p. 141 - 143 (2015/02/19)
An organocatalytic regioselective synthes is of aurones from o-alkynoylphenols was achieved. A catalytic amount of tributylphosphine select ively induced the 5-exo cyclization of o-alkynoylphenols under ambient conditions leading to aurone derivatives in high to excellent yields.
Copper-catalyzed intramolecular tandem reaction of (2-halogenphenyl)(3- phenyloxiran-2-yl)methanones: Synthesis of (Z)-aurones
Weng, Yiyi,Chen, Qixu,Su, Weike
, p. 4218 - 4224 (2014/05/20)
A convenient and efficient method for the copper-catalyzed synthesis of (Z)-aurones via intramolecular tandem reaction of (2-halogenphenyl)(3- phenyloxiran-2-yl)methanones is reported. Moreover, a plausible mechanism for the formation of (Z)-aurones is proposed. This is the first report on the synthesis of (Z)-aurones through copper-catalyzed Ullmann coupling reaction employing epoxides as substrates.
In vitro inhibitory properties of ferrocene-substituted chalcones and aurones on bacterial and human cell cultures
Tiwari, Keshri Nath,Monserrat, Jean-Philippe,Hequet, Arnaud,Ganem-Elbaz, Carine,Cresteil, Thierry,Jaouen, Gerard,Vessieres, Anne,Hillard, Elizabeth A.,Jolivalt, Claude
experimental part, p. 6451 - 6457 (2012/09/21)
Two series of ten chalcones and ten aurones, where ferrocene replaces the C ring and with diverse substituents on the A ring were synthesized. The compounds were tested against two antibiotic-sensitive bacterial strains, E. coli ATCC 25922 and S. aureus ATCC 25923, and two antibiotic-resistant strains, S. aureus SA-1199B and S. epidermidis IPF896. The unsubstituted compound and those with methoxy substitution showed an inhibitory effect on all bacterial strains at minimum inhibitory concentrations ranging between 2 and 32 mg L -1. For four of these compounds, the effect was bactericidal, as opposed to bacteriostatic. The corresponding organic aurones did not show growth inhibition, underscoring the role of the ferrocene group. The methoxy-substituted aurones and the unsubstituted aurone also showed low micromolar (IC50) activity against MRC-5 non-tumoral lung cells and MDA-MB-231 breast cancer cells, suggesting non-specific toxicity.
Identification of the major degradation products of 4-methoxy-2-(3- phenyl-2-propynyl)phenol formed by exposure to air and light
Schiavi,Serafini,Italia,Villa,Fronza,Selva
, p. 812 - 814 (2007/10/02)
Exposure of 4-methoxy-2-(3-phenyl-2-propynyl)phenol (CO/1828) to air and light (accelerated by temperature) yields 1-(2-hydroxy-5-methoxyphenyl)-3- phenylpropynone as the major degradation product. With extraction, this product rapidly degrades to 5-methoxyaurone and 6-methoxyflavone. In addition, a mixture of dimeric and heterodimeric compounds that are not fully identified was observed. These results indicate the formation of a reactive ortho-quinone methide as an unstable intermediate. This hypothesis is supported by evidence that the aurone slowly isomerizes into the flavone in control samples. Identification of compounds was accomplished with mass spectrometry, nuclear magnetic resonance spectrometry, UV-high-performance liquid chromatography, and comparison with authentic samples.
6-Endo-Dig vs. 5-Exo-Dig Ring Closure in o-Hydroxyaryl Phenylethynyl Ketones. A New Approach to the Synthesis of Flavones and Aurones
Garcia, Hermenegildo,Iborra, Sara,Primo, Jaime,Miranda, Miguel A.
, p. 4432 - 4436 (2007/10/02)
The aryl phenylpropynoates 3a-c, prepared by esterification of phenylpropynoic acid with the corresponding phenols, by means of N,N'-dicyclohexylcarbodiimide, give upon irradiation the o-hydroxyaryl phenylethynyl ketones 4a-c.The cyclization of these compounds in basic media follows two alternative pathways: 6-endo-dig ring closure, to give the flavones 8a-c, and /or 5-exo-dig ring closure , to give the aurones 9a-c.The predominance of one or the other cyclization mode is strongly influenced by the reaction conditions.Thus, the use of potassium carbonate in acetoneas cyclizing reagent favors the 6-endo-dig process, while the 5-exo-dig process becomes clearly enhanced when using sodium ethoxide or potassium carbonate in ethanol.The mechanistic implications of these facts are discussed within the framework of Baldwin's rules.From the preparative point of view, the above results disclose the synthetic possibilities of the key ketones 4 as precursors of flavones and aurones.
