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【结 构 式】 
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【药物名称】 【化学名称】N-[2-(N-tert-Butylcarbamoylsulfanyl)benzoyl]-beta-alaninamide 【CA登记号】 【 分 子 式 】C15H21N3O3S 【 分 子 量 】323.41692 |
【开发单位】Achillion (Originator), National Institutes of Health (Originator), Southern Research Institute (Originator) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY |
合成路线1
2,2'-Dithiosalicylic acid (I) is activated as the bis-succinimidyl ester (II) upon treatment with N-hydroxysuccinimide and DIC. Coupling of the active ester (II) with 3-aminopropionamide (III) gives rise to the corresponding dithiosalicylamide (IV). Reductive cleavage of the disulfide bond of (IV) using tris(2-carboxyethyl)phosphine (TCEP) affords thiol (V). The desired thiolcarbamate is then obtained by condensation of (V) with tert-butyl isocyanate in DMF.
| 【1】 Goel, A.; et al.; Benzamide-based thiocarbamates: A new class of HIV-1 NCp7 inhibitors. Bioorg Med Chem Lett 2002, 12, 5, 767. |
| 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) | 20404 | 2-[(2-carboxyphenyl)disulfanyl]benzoic acid; 2,2'-Dithiodibenzoic acid | 119-80-2 | C14H10O4S2 | 详情 | 详情 |
| (II) | 58510 | 1-({2-[(2-{[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}phenyl)disulfanyl]benzoyl}oxy)-2,5-pyrrolidinedione | C22H16N2O8S2 | 详情 | 详情 | |
| (III) | 58511 | 3-aminopropanamide | C3H8N2O | 详情 | 详情 | |
| (IV) | 58512 | N-(3-amino-3-oxopropyl)-2-[(2-{[(3-amino-3-oxopropyl)amino]carbonyl}phenyl)disulfanyl]benzamide | C20H22N4O4S2 | 详情 | 详情 | |
| (V) | 58513 | N-(3-amino-3-oxopropyl)-2-sulfanylbenzamide | C10H12N2O2S | 详情 | 详情 |