新产品编号:889593
Chemical Name: 8-(4'-Bromobiphenyl-4-yl)-8-oxooctanohydroxamic acid
CAS No. 362670-51-7
项目整合开发状态: Biological Testing
项目研究机构: MethylGene (Originator)
合成路线:The reaction of ethyl 7-bromoheptanoate (I) with NaI,Zn,dibromoethane,LiCl and CuCN gives the organometallic derivative (II),which is condensed with 4-bromobenzoyl chloride (III) in THF to yield 8-(4-bromophenyl)-8-oxooctanoic acid ethyl ester (IV).The condensation of (IV) with 4-bromophenylboronic acid (V) by means of Pd(PPh3)4 and K2CO3 in hot toluene affords 8-(4'-bromobiphenyl-4-yl)-8-oxooctanoic acid ethyl ester (VI),which is hydrolyzed with NaOH in THF/methanol to provide the corresponding carboxylic acid (VII).Finally,this compound is treated with hydroxylamine,EDC,HOBt and TEA to obtain the target hydroxamic acid.
📌 参考资料/链接：
参考文献标题:Inhibitors of histone deacetylase
文献作者:Delorme,D.; Woo,S.H.; Vaisburg,A.(MethylGene Inc.)
参考来源:WO 0170675
📄 详细内容
合成路线:The reaction of ethyl 7-bromoheptanoate (I) with NaI,Zn,dibromoethane,LiCl and CuCN gives the organometallic derivative (II),which is condensed with 4-bromobenzoyl chloride (III) in THF to yield 8-(4-bromophenyl)-8-oxooctanoic acid ethyl ester (IV).The condensation of (IV) with 4-bromophenylboronic acid (V) by means of Pd(PPh3)4 and K2CO3 in hot toluene affords 8-(4'-bromobiphenyl-4-yl)-8-oxooctanoic acid ethyl ester (VI),which is hydrolyzed with NaOH in THF/methanol to provide the corresponding carboxylic acid (VII).Finally,this compound is treated with hydroxylamine,EDC,HOBt and TEA to obtain the target hydroxamic acid.
参考文献标题:Structurally simple trichostatin A-like straight chain hydroxamates as potent histone deacetylase inhibitors
文献作者:Woo,S.H.; et al.
参考来源:J Med Chem 2002,45(13),2877