合成路线:In a different method,p-aminocinnamic acid (I) is acylated by 3,4-dimethoxybenzenesulfonyl chloride (II) to yield sulfonamide (III).After activation of the carboxylic acid (III) with oxalyl chloride,the resultant acid chloride (IV) is condensed with hydroxylamine to furnish the target hydroxamic acid.
参考文献标题:Carbamic acid cpds.comprising a sulfonamide linkage as HDAC inhibitors
文献作者:Harris,C.J.; Finn,P.W.; Kalvinsh,I.; Piskunova,I.; Starchenkov,I.; Watkins,C.J.; Romero-Martin,M.-R.; Moore,K.G.; Ritchie,J.; Loza,E.; Dikovska,K.; Gailite,V.; Vorona,M.; Adrianov,V.; Duffy,J.E.S.(TopoTarget A/S)
参考来源:EP 1328510; WO 0230879
合成路线:Acylation of 4-iodoaniline (I) with 3,4-dimethoxybenzenesulfonyl chloride (II),followed by basic methanolysis leads to sulfonamide (III).Heck coupling of aryl iodide (III) with acrylic acid (IV) in the presence of tris(dibenzylideneacetone)dipalladium and tri(o-tolyl)phosphine gives the cinnamic acid derivative (V).This is then coupled to the tetrahydropyranyl-protected hydroxylamine (VI) by means of EDC/HOBt to furnish (VII).The tetrahydropyranyl hydroxamate (VII) is finally deprotected under acidic conditions to produce the title compound.
参考文献标题:Design and synthesis of a novel class of histone deacetylase inhibitors
文献作者:Lavoie,R.; Bouchain,G.; Frechette,S.; Woo,S.H.; Abou-Khalil,E.; Leit,S.; Fournel,M.; Yan,P.T.; Trachy-Bourget,M.C.; Beaulieu,C.; Li,Z.; Besterman,J.M.; Delorme,D.
参考来源:Bioorg Med Chem Lett 2001,11(21),2847
合成路线:Acylation of 4-iodoaniline (I) with 3,4-dimethoxybenzenesulfonyl chloride (II),followed by basic methanolysis leads to sulfonamide (III).Heck coupling of aryl iodide (III) with acrylic acid (IV) in the presence of tris(dibenzylideneacetone)dipalladium and tri(o-tolyl)phosphine gives the cinnamic acid derivative (V).This is then coupled to the tetrahydropyranyl-protected hydroxylamine (VI) by means of EDC/HOBt to furnish (VII).The tetrahydropyranyl hydroxamate (VII) is finally deprotected under acidic conditions to produce the title compound.
参考文献标题:Development of potential antitumor agents.Synthesis and biological evaluation of a new set of sulfonamide derivatives as histone deacetylase inhibitors
文献作者:Bouchain,G.; Leit,S.; Frechette,S.; Khalil,E.A.; Lavoie,R.; Moradei,O.; Woo,S.H.; Fournel,M.; Yan,P.T.; Kalita,A.; Trachy-Bourget,M.C.; Beaulieu,C.; Li,Z.; Robert,M.F.; MacLeod,A.R.; Besterman,J.M.; Delorme,D.
参考来源:J Med Chem 2003,46(5),820
产品链接: CAS No.414872-01-8››