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【结 构 式】

【药物名称】

【化学名称】3-Chloro-5,8-dimethoxy-3-(3-methoxyphenoxy)-1,4-naphthoquinone

【CA登记号】

【 分 子 式 】C19H15ClO6

【 分 子 量 】374.7808

【开发单位】Memorial Sloan-Kettering Cancer Center (Originator)

【药理作用】Oncolytic Drugs

合成路线1

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.

1 Chang, H.-X.; Chou, T.C.; Savaraj, N.; Liu, L.F.; Yu, C.; Cheng, C.C.; 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. J Med Chem 1999, 42, 3, 405.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 21946 1,4-dimethoxybenzene; 4-methoxyphenyl methyl ether 150-78-7 C8H10O2 详情 详情
(II) 21947 3,4-dichloro-2,5-furandione 1122-17-4 C4Cl2O3 详情 详情
(III) 21948 2,3-dichloro-5,8-dihydroxynaphthoquinone 14918-69-5 C10H4Cl2O4 详情 详情
(IV) 21951 2,3-dichloro-5,8-dimethoxynaphthoquinone C12H8Cl2O4 详情 详情
(V) 21950 6,7-dichloro-5,8-dimethoxynaphthoquinone C12H8Cl2O4 详情 详情
(VI) 22389 3-Methoxyphenol 150-19-6 C7H8O2 详情 详情
Extended Information