网站主页>>>项目整合精选>>>项目整合精选>>>新产品编号:1497081

新产品编号:1497081

Chemical Name: 3-Chloro-5,8-dimethoxy-3-(3-methoxyphenoxy)-1,4-naphthoquinone
项目整合开发状态: Biological Testing
项目研究机构: Memorial Sloan-Kettering Cancer Center (Originator)
合成路线:Friedel Crafts condensation of p-dimethoxybenzene (I) with dichloromaleic anhydride (II) in a molten mixture of AlCl3 and NaCl yielded dichloronaphthazarin (III).Finally,treatment of (III) with resorcinol (IV) and Na2CO3 in DMSO at room temperature furnished the target compound.

合成路线:Friedel Crafts condensation of p-dimethoxybenzene (I) with dichloromaleic anhydride (II) in a molten mixture of AlCl3 and NaCl yielded dichloronaphthazarin (III).Subsequent methylation of (III) with CH3I in the presence of Ag2O in CHCl3 gave a mixture of dimethoxy naphthoquinones (IV) and (V),from which the desired isomer (IV) was isolated by recrystallization from CHCl3-CCl4.Finally,treatment of (IV) with 3-methoxyphenol (VI) and Na2CO3 in DMSO at room temperature furnished the target compound.

合成路线:Friedel Crafts condensation of p-dimethoxybenzene (I) with dichloromaleic anhydride (II) in a molten mixture of AlCl3 and NaCl yielded dichloronaphthazarin (III).Subsequent methylation of (III) with CH3I in the presence of Ag2O in CHCl3 gave a mixture of dimethoxy naphthoquinones (IV) and (V),from which the desired isomer (IV) was isolated by recrystallization from CHCl3-CCl4.Finally,treatment of (IV) with 3,5-dimethoxyphenol (VI) and Na2CO3 in DMSO at room temperature furnished the target compound.
📌 参考资料/链接:
参考文献标题:Design of antineoplastic agents based on the "2-phenylnaphthalene-type" structural pattern.4.Synthesis and biological activity of 2-chloro-3-(substituted phenoxy)-1,4-naphthoquinones and related 5,8-dihydroxy-1,4-naphthoquinones
文献作者:Chang,H.-X.; Chou,T.C.; Savaraj,N.; Liu,L.F.; Yu,C.; Cheng,C.C.
参考来源:J Med Chem 1999,42(3),405