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【结 构 式】 
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【药物名称】 【化学名称】3-Chloro-5,8-dimethoxy-2-[3,5-(dimethoxy)phenoxy]-1,4-naphthoquinone 【CA登记号】 【 分 子 式 】C20H17ClO7 【 分 子 量 】404.80729 |
【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 3,5-dimethoxyphenol (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) | 22390 | 3,5-dimethoxyphenol | 500-99-2 | C8H10O3 | 详情 | 详情 |
Extended Information