【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