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【结 构 式】 
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【药物名称】Nevadensin 【化学名称】5,7-Dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one 【CA登记号】10176-66-6 【 分 子 式 】C18H16O7 【 分 子 量 】344.32402 |
【开发单位】Shanghai Institute Materia Medica (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Antimycobacterial Agents |
合成路线1
Nevadensin can be synthesized starting from methyl 2,6-dimethoxyphenyl acetate (I). This compound is nitrated and then hydrogenated, giving methyl 3,5-diamino-2,6-dimethoxyphenyl acetate (III). Treatment of the latter compound with stannous chloride-hydrochloric acid gives dimethoxyphloroglucinol (IV). Introduction of an acetyl group followed by interaction with p-methoxybenzoyl chloride (A) gives 4-acetyl-2,6-dimethoxyphloroglucinyl tri(p-methoxy) benzoate (VI). The latter compound, after being rearranged, is cyclized into 5,7-di(p-methoxy)benzoylnevadensin (VIII). Nevadensin can readily be obtained by the hydrolysis of the compound (VIII).
| 【1】 Feng, S.; Xu, Y.; Fan, G.; Studies on the antituberculosis principles from Lysionotus pauciflora Maxim. I. Isolation and identification of nevadensin. Acta Pharm Sin 1979, 14, 7, 447-448. |
| 【2】 Su, C.; Han, G.; Zhang, Y.; Determination of nevadensin in biological specimens and its pharmacokinetic study. Chin Pharm Bull 1981, 2, 3, 182-185. |
| 【3】 Ru-yun, J.; Nevadensin. Drugs Fut 1984, 9, 4, 271. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 22671 | 4-Methoxybenzoyl chloride; p-Methoxybenzoyl chloride; 4-Anisoyl chloride | 100-07-2 | C8H7ClO2 | 详情 | 详情 |
| (I) | 34188 | 2,6-dimethoxyphenyl acetate | C10H12O4 | 详情 | 详情 | |
| (II) | 34189 | 2,6-dimethoxy-3,5-dinitrophenyl acetate | C10H10N2O8 | 详情 | 详情 | |
| (III) | 34190 | 3,5-diamino-2,6-dimethoxyphenyl acetate | C10H14N2O4 | 详情 | 详情 | |
| (IV) | 34191 | 2,4-dimethoxy-1,3,5-benzenetriol | C8H10O5 | 详情 | 详情 | |
| (V) | 34192 | 1-(2,4,6-trihydroxy-3,5-dimethoxyphenyl)-1-ethanone | C10H12O6 | 详情 | 详情 | |
| (VI) | 34193 | 2-acetyl-4,6-dimethoxy-3,5-bis[(4-methoxybenzoyl)oxy]phenyl 4-methoxybenzoate | C34H30O12 | 详情 | 详情 | |
| (VII) | 34194 | 3-hydroxy-2,6-dimethoxy-5-[(4-methoxybenzoyl)oxy]-4-[3-(4-methoxyphenyl)-3-oxopropanoyl]phenyl 4-methoxybenzoate | C34H30O12 | 详情 | 详情 | |
| (VIII) | 34195 | 6,8-dimethoxy-5-[(4-methoxybenzoyl)oxy]-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl 4-methoxybenzoate | C34H28O11 | 详情 | 详情 |