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【结 构 式】 
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【药物名称】Adamantyl-SNO, NMI-1165 【化学名称】N,N-Dimethyl-2-[2-(nitrososulfanyl)adamant-2-yl]acetamide 【CA登记号】 【 分 子 式 】C14H22N2O2S 【 分 子 量 】282.40764 |
【开发单位】NitroMed (Originator) 【药理作用】CARDIOVASCULAR DRUGS, Restenosis Treatment of, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Nitric Oxide Donors |
合成路线1
Thionation of 2-adamantanone (I) by means of P4S10 gives thioketone (II). Subsequent addition of tert-butyl acetate to thioadamantanone (II) furnishes the beta-mercapto ester (III). After acidic cleavage of the tert-butyl ester of (III), the resultant mercapto acid (IV) is cyclized to the thiolactone (V) by using EDC. Subsequent lactone ring opening in (V) with dimethylamine gives rise to amide (VI). Finally, the thiol group of (VI) is nitrosated with tert-butyl nitrite to provide the desired nitrosothio compound.
| 【1】 Lin, C.-E.; et al.; Design and synthesis of nitrosylated paclitaxel (NO-paclitaxel) and adamantanyl nitric oxide donor as antirestenosis agents. 223rd ACS Natl Meet (April 7 2002, Orlando) 2002, Abst MEDI 36. |
| 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) | 40404 | 2-adamantanone | 700-58-3 | C10H14O | 详情 | 详情 |
| (II) | 58354 | 2-adamantanethione | C10H14S | 详情 | 详情 | |
| (III) | 58355 | tert-butyl 2-(2-sulfanyl-2-adamantyl)acetate | C16H26O2S | 详情 | 详情 | |
| (IV) | 58356 | 2-(2-sulfanyl-2-adamantyl)acetic acid | C12H18O2S | 详情 | 详情 | |
| (V) | 58357 | C12H16OS | 详情 | 详情 | ||
| (VI) | 58358 | N,N-dimethyl-2-(2-sulfanyl-2-adamantyl)acetamide | C14H23NOS | 详情 | 详情 |