444711-04-0Relevant articles and documents
Aurone derivatives as promising antibacterial agents against resistant Gram-positive pathogens
Olleik, Hamza,Yahiaoui, Samir,Roulier, Brayan,Courvoisier-Dezord, Elise,Perrier, Josette,Pérès, Basile,Hijazi, Akram,Baydoun, Elias,Raymond, Josette,Boumendjel, Ahcène,Maresca, Marc,Haudecoeur, Romain
, p. 133 - 141 (2019/01/23)
A set of variously substituted aurones was synthesized and evaluated against Methicillin-Resistant S. aureus (MRSA) and P. aeruginosa. Several analogues were found active against MRSA, but no effect was recorded against P. aeruginosa. Compounds 27, 30 and 33 showed low cytotoxicity, and were tested against a full range of bacterial (Gram-positive and Gram-negative) and fungal species, including resistant strains. These aurones displayed a selective inhibition of Gram-positive bacteria with excellent Therapeutic Index values, while showing no significant action on several Gram-negative strains, H. pylori and V. alginolyticus being the only susceptible strains among the Gram-negative bacteria tested. A permeabilization assay showed that the antibacterial activity of at least some of the aurones could be linked to alterations of the bacterial membrane. Overall, this study endorses the use of the aurone scaffold for the development of new potent and selective antibacterial agents.
Discovery of benzylidenebenzofuran-3(2H)-one (aurones) as inhibitors of tyrosinase derived from human melanocytes
Okombi, Sabrina,Rival, Delphine,Bonnet, Sébastien,Mariotte, Anne-Marie,Perrier, Eric,Boumendjel, Ahcène
, p. 329 - 333 (2007/10/03)
Tyrosinase is a copper-dependent enzyme which converts L- tyrosine to dopaquinone and is involved in different biological processes such as melanogenesis and skin hyperpigmentation. The purpose of this study was to investigate naturally occurring aurones (Z-benzylidenebenzofuran-3(2H)-one) and analogues as human tyrosinase inhibitors. Several aurones bearing hydroxyl groups on A-ring and different substituents on B-ring were synthesized and evaluated as inhibitors of human melanocyte-tyrosinase by an assay which measures tyrosinase-catalyzed L-Dopa oxidation. We found that unsubstituted aurones were weak inhibitors; however, derivatives with two or three hydroxyl groups preferably at 4,6 and 4′ positions are able to induce significant tyrosinase inhibition. The most potent aurone was found to be the naturally occurring 4,6,4′-trihydroxyaurone which induces 75% inhibition at 0.1 mM concentration and is highly effective when compared to kojic acid, one of the best tyrosinase inhibitors known so far (the latter is completely inactive at such concentrations). Active aurones are devoid of toxic effects as shown by in vivo studies.
A method of cosmetic depigmentation care by applying at least one aurone
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Page/Page column 13, (2008/06/13)
At least one aurone or a natural or synthetic derivative of aurone, or an analogue of aurone, in which the independent phenyl ring can be substituted by a heterocycle of pyrrole, imidazole, triazole, pyridine, furan, or thiophene type, is disclosed as a cosmetic agent, or as an active substance, for the manufacture either of a cosmetic composition, or of a pharmaceutical composition, notably a dermatological composition, having a melanogenesis-inhibiting activity or a depigmenting activity, or an anti-tyrosinase activity.
Synthesis of substituted 2,3-dihydrobenzofuran in a process involving a facile acyl migration
Li, Wen-Sen,Guo, Zhenrong,Thornton, John,Katipally, Kishta,Polniaszek, Richard,Thottathil, John,Vu, Truc,Wong, Michael
, p. 1923 - 1925 (2007/10/03)
Reduction of 2,6-diacetoxy-2′-bromoacetophenone (10) with NaBH4 led to 3,4-diacetoxydihydrobenzofuran (12) in a process involving acyl migration followed by cyclization. Subsequent hydrogenolysis gave 4-acetoxydihydrobenzofuran which, upon saponification, afforded 4-hydroxydihydrobenzofuran (8) in good yield. This approach is shown to be a general method for preparation of substituted dihydrobenzofurans.
