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【结 构 式】 
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【药物名称】S-24718 【化学名称】1-[8-(Benzylamino)-3,4-dihydrospiro[2H-1,4-benzoxazine-3,1'-cyclopentan]-5-yl]-1-phenylmethanone 【CA登记号】251562-03-5 【 分 子 式 】C26H26N2O2 【 分 子 量 】398.50932 |
【开发单位】Servier (Originator) 【药理作用】Cerebrovascular Diseases, Treatment of, NEUROLOGIC DRUGS, Antioxidants |
合成路线1
The electrochemical oxidation of 3,4-dihydroxy-2-methoxybenzophenone (I) in the presence of (1-aminocyclopentyl)methanol (II) using tetraethylammonium perchlorate as the supporting electrolyte led to the formation of a transient ortho-quinone (III), which, by intramolecular ring closure with amino alcohol (II), gave rise to the benzoxazinone (IV). Subsequent condensation of (IV) with benzylamine (V) produced the Schiff base (VI). This was finally converted to the title compound by electrochemical reduction.
| 【1】 Largeron, M.; et al.; Synthesis and in vitro evaluation of new-8-amino-1,4-benzoxazine derivatives as neuroprotective antioxidants. J Med Chem 1999, 42, 24, 5043. |
| 【2】 Largeron, M.; Lestage, P.; Fleury, M.B.; Lockhart, B. (ADIR et Cie.); Novel 8-amino-1,4-benzoxazine cpds., preparation method and pharmaceutical compsns. containing them. FR 2779144; WO 9962889 . |
| 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) | 52081 | (3,4-dihydroxy-2-methoxyphenyl)(phenyl)methanone | C14H12O4 | 详情 | 详情 | |
| (II) | 52082 | 1-Amino-1-cyclopentanemethanol; cycloleucinol | 10316-79-7 | C6H13NO | 详情 | 详情 |
| (III) | 52083 | 4-benzoyl-3-methoxybenzo-1,2-quinone | C14H10O4 | 详情 | 详情 | |
| (IV) | 52084 | C19H19NO4 | 详情 | 详情 | ||
| (V) | 15147 | Benzylamine; Phenylmethanamine | 100-46-9 | C7H9N | 详情 | 详情 |
| (VI) | 52085 | C26H26N2O3 | 详情 | 详情 |