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新产品编号:2027051

Chemical Name: 4-[5-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)isoxazol-3-yl]benzoic acid
项目整合开发状态: Biological Testing
项目研究机构: Universit?degli Studi di Bologna (Originator), Universit?degli Studi di Palermo (Originator), Universit?di Ferrara (Originator), University of Oklahoma Health Sci. Cent. (Originator)
合成路线:Wittig reaction of aldehyde (I) with methylene triphenylphosphorane produced olefin (II).Oxime (IV) was prepared from methyl 4-formylbenzoate (III) by treatment with hydroxylamine.The nitrile oxide generated from imine (IV) by chlorination,followed by elimination under basic conditions,underwent a [3+2] regioselective cycloaddition with alkene (II) to produce isoxazoline (V).Oxidation of the isoxazoline ring of (V) to the corresponding isoxazole derivative (VI) was accomplished by treatment with N-bromosuccinimide.Finally,ester hydrolysis with LiOH furnished the title carboxylic acid.
📌 参考资料/链接:
参考文献标题:Heterocycle-containing retinoids.Discovery of a novel isoxazole arotinoid possessing potent apoptotic activity in multidrug and drug-induced apoptosis-resistant cells
文献作者:Simoni,D.; Roberti,M.; Invidiata,F.P.; Rondanin,R.; Baruchello,R.; Malagutti,C.; Mazzali,A.; Rossi,M.; Grimaudo,S.; Capone,F.; Dusonchet,L.; Meli,M.; Raimondi,M.V.; Landino,M.; D'Alessandro,N.; Tolomeo,M.; Arindam,D.; Lu,S.; et al.
参考来源:J Med Chem 2001,44(14),2308