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【结 构 式】 
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【药物名称】 【化学名称】N1-[2-Hydroxytetrahydrofuran-3(S)-yl]-N2-(phenylaminocarbonothioyl)-L-leucinamide 【CA登记号】 【 分 子 式 】C17H25N3O3S 【 分 子 量 】351.4711 |
【开发单位】Senju (Originator) 【药理作用】Anticataract Agents, OCULAR MEDICATIONS, Ophthalmic Drugs, Calpain Inhibitors |
合成路线1
N-Boc-L-Leucine (I) is activated as the corresponding succinimidyl ester (II) upon treatment with N-hydroxysuccinimide and EDC. Coupling of active ester (II) with (S)-alpha-amino-gamma-butyrolactone (III) affords amide (IV). After N-Boc group deprotection of (IV) under acidic conditions, the resultant amine (V) is condensed with phenyl isothiocyanate to furnish thiourea (VI). Finally, reduction of the lactone function of (VI) with DIBAL gives rise to the target cyclic hemiacetal compound.
| 【1】 Nakamura, M.; Yamaguchi, M.; Sakai, O.; Inoue, J.; Exploration of cornea permeable calpain inhibitors as anticataract agents. Bioorg Med Chem 2003, 11, 7, 1371. |
| 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) | 31819 | (2R)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoic acid | 16937-99-8 | C11H21NO4 | 详情 | 详情 |
| (II) | 64224 | tert-butyl (1S)-1-{[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}-3-methylbutylcarbamate | C15H24N2O6 | 详情 | 详情 | |
| (III) | 64228 | (3S)-3-aminodihydro-2(3H)-furanone;L-homoserine lactone;(S)-3-aminodihydrofuran-2(3H)-one | C4H7NO2 | 详情 | 详情 | |
| (IV) | 64225 | tert-butyl (1S)-3-methyl-1-({[(3S)-2-oxotetrahydro-3-furanyl]amino}carbonyl)butylcarbamate | C15H26N2O5 | 详情 | 详情 | |
| (V) | 64226 | (2S)-2-amino-4-methyl-N-[(3S)-2-oxotetrahydro-3-furanyl]pentanamide | C10H18N2O3 | 详情 | 详情 | |
| (VI) | 64227 | (2S)-2-[(anilinocarbothioyl)amino]-4-methyl-N-[(3S)-2-oxotetrahydro-3-furanyl]pentanamide | C17H23N3O3S | 详情 | 详情 |
Extended Information