新产品编号:840551
Chemical Name: 4,5-Dimethoxy-2-[3-[4-[3-(4-nitrophenyl)ureido]phenyl]propionamido]benzoic acid ethyl ester
CAS No. 334025-33-1
项目整合开发状态: Biological Testing
项目研究机构: Japan Energy (Originator)
合成路线:Acylation of 2-amino-4,5-dimethoxyacetophenone (I) with 4-nitrocinnamoyl chloride (II) affords amide (III).Simultaneous double bond hydrogenation and nitro group reduction in (III) with hydrogen and Pd/C leads to aniline (IV).This is finally condensed with 4-nitrophenyl isocyanate (V) in the presence of DMAP to produce the corresponding urea
合成路线:Fischer esterification of 4,5-dimethoxy-2-nitrobenzoic acid (I) with H2SO4 in EtOH affords the corresponding ethyl ester (II).Subsequent nitro group reduction in (II) by hydrogenation over Pd/C provides amino ester (III) (1).Acylation of (III) with 4-nitrocinnamoyl chloride (IV) furnishes amide (V).Simultaneous double bond hydrogenation and nitro group reduction in (V) with H2 and Pd/C leads to amine (VI).This is finally coupled with 4-nitrophenyl isocyanate (VII) in the presence of DMAP to yield the target diaryl urea derivative (1,2).
📌 参考资料/链接：
参考文献标题:Novel diarylamide derivs.and use thereof as medicines
文献作者:Takaku,H.; Isobe,Y.; Ogita,H.(Japan Energy Corp.)
参考来源:EP 1229010; WO 0125190
📄 详细内容
合成路线:Fischer esterification of 4,5-dimethoxy-2-nitrobenzoic acid (I) with H2SO4 in EtOH affords the corresponding ethyl ester (II).Subsequent nitro group reduction in (II) by hydrogenation over Pd/C provides amino ester (III) (1).Acylation of (III) with 4-nitrocinnamoyl chloride (IV) furnishes amide (V).Simultaneous double bond hydrogenation and nitro group reduction in (V) with H2 and Pd/C leads to amine (VI).This is finally coupled with 4-nitrophenyl isocyanate (VII) in the presence of DMAP to yield the target diaryl urea derivative (1,2).
参考文献标题:Synthesis of potent and selective inhibitors against the proliferation of human coronary artery smooth muscle cells
文献作者:Ogita,H.; Isobe,Y.; Takaku,H.; Sekine,R.; Goto,Y.; Misawa,S.; Hayashi,H.
参考来源:Chem Pharm Bull 2003,51(2),117