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【结 构 式】 
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【药物名称】CEB-1370 【化学名称】1-[3-(3,5-Di-tert-butyl-4-hydroxyphenyl)propyl]-3-hydroxy-2-methylpyridin-4(1H)-one methanesulfonate 【CA登记号】224563-84-2, 224563-83-1 (free base) 【 分 子 式 】C24H37NO6S 【 分 子 量 】467.62959 |
【开发单位】Vernalis Research (Originator) 【药理作用】Antagonists to Metals, Cerebrovascular Diseases, Treatment of, NEUROLOGIC DRUGS, Specific Antidotes, Stroke, Treatment of, TREATMENT OF POISONING, DRUG ABUSE & DEPENDENCY, Lipid Peroxidation Inhibitors |
合成路线1
Catalytic hydrogenation of 3,5-di-tert-butyl-4-hydroxycinnamic acid (I) afforded the saturated carboxylic acid (II), which was converted into amide (IV) via the corresponding acid chloride (III). Reduction of the amide function of (IV) by means of LiAlH4 furnished the primary amine (V). This was condensed with O-benzyl maltol (VI) to produce the pyridone (VII). After hydrogenolysis of the benzyl protecting group of (VII), the title compound was isolated as the corresponding mesylate salt.
| 【1】 Malcolm, C.S.; Bebbington, D.; Monck, N.J.T.; Palmer, A.M.; Gaur, S.; Benwell, K.; Porter, R.H.P.; Harvey, V.; 3,5-Disubstituted-4-hydroxyphenyls linked to 3-hydroxy-2-methyl-4(1H)-pyridinone: Potent inhibitors of lipid peroxidation and cell toxicity. J Med Chem 2000, 43, 15, 2779. |
| 【2】 Malcolm, C.; Porter, R.; Bebbington, D.; Palmer, A.; Gaur, S.; Monck, N. (Vernalis Research Ltd.); Ortho-hydroxypyridinone derivs. as iron chelating and antioxidant agents. EP 1027335; WO 9923075 . |
| 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) | 43375 | (E)-3-[3,5-di(tert-butyl)-4-hydroxyphenyl]-2-propenoic acid | 22014-01-3 | C17H24O3 | 详情 | 详情 |
| (II) | 43376 | 3-[3,5-di(tert-butyl)-4-hydroxyphenyl]propionic acid | 20170-32-5 | C17H26O3 | 详情 | 详情 |
| (III) | 43777 | 5,5,8,8-tetramethyl-N-(2-nitrophenyl)-5,6,7,8-tetrahydro-2-naphthalenamine; N-(2-nitrophenyl)-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)amine | C20H24N2O2 | 详情 | 详情 | |
| (IV) | 43378 | 3-[3,5-di(tert-butyl)-4-hydroxyphenyl]propanamide | C17H27NO2 | 详情 | 详情 | |
| (V) | 43379 | 4-(3-aminopropyl)-2,6-di(tert-butyl)phenol | C17H29NO | 详情 | 详情 | |
| (VI) | 12074 | 3-(Benzyloxy)-2-methyl-4H-pyran-4-one；3-(benzyloxy)-2-methylpyran-4-one | 61049-69-2 | C13H12O3 | 详情 | 详情 |
| (VII) | 43380 | 3-(benzyloxy)-1-[3-[3,5-di(tert-butyl)-4-hydroxyphenyl]propyl]-2-methyl-4(1H)-pyridinone | C30H39NO3 | 详情 | 详情 |