57060-61-4Relevant articles and documents
Metal-free methodology for the preparation of sterically hindered alkynoylphenols and its application to the synthesis of flavones and aurones
Taylor, Cassandra,Bolshan, Yuri
, p. 4392 - 4396 (2015/06/22)
A metal-free synthesis for the preparation of sterically demanding ortho-demethylated ynones from mixed anhydrides and potassium alkynyltrifluoroborate salts has been developed. The one-pot reaction proceeds rapidly in the presence of a Lewis acid without the exclusion of air and moisture. This method is advantageous in that it is operationally simple, proceeds under mild conditions, and has a broad substrate scope. 2,6-Dimethoxy substituted anhydrides afford the corresponding mono-demethylated ynone products in good yields. In particular, 2-hydroxy substituted ynone products are valuable synthetic intermediates because their conversion to biologically active natural product scaffolds is straightforward. Flavones were obtained via 6-endo cyclization of the o-alkynyoylphenol intermediates under acidic conditions. Cesium carbonate was found to promote rapid 5-exo cyclization to furnish aurone products.
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.
Reactions of carbanions with 1,3-benzodioxin-4-ones: Facile routes to flavones, aurones, and acyl phloroglucinols
Kraus, George A.,Wie, Jingqiang,Thite, Aniket
experimental part, p. 2427 - 2431 (2009/04/06)
Two 1,3-benzodioxin-4-ones react with enolates, acetylides and aryllithium reagents to afford adducts that were converted into flavones, aurones, and an acyl phloroglucinol. Georg Thieme Verlag Stuttgart.
