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【结 构 式】 
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【药物名称】 【化学名称】2-(2-Adamantyl)piperidine 【CA登记号】 【 分 子 式 】C15H25N 【 分 子 量 】219.3732 |
【开发单位】National Hellenic Research Foundation (Originator), Rega Institute for Medical Research (Originator), University of Athens (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Anti-Influenza A Virus Drugs, Anti-Influenza Virus Drugs, Antiviral Drugs |
合成路线1
The condensation of adamantan-2-one (I) with 2-pyridyllithium (II) in THF/ethyl ether gives 2-(2-pyridyl)adamantan-2-ol (III), which is treated with dry HCl in ethanol to yield the pyridinium salt (IV). The hydrogenation of (IV) with H2 over PtO2 in ethanol affords 2-(2-piperidinyl)adamantan-2-ol (V), which is treated with SOCl2 in refluxing dichloromethane to provide the piperidinium chloride (VI). The dehydrochlorination of (VI) with KOH in refluxing ethanol yields the tetrahydropyridine (VIII), which is finally hydrogenated with NaBH4 in methanol.
| 【1】 Foscolos, G.B.; De Clercq, E.; Kolocouris, A.; Tataridis, D.; Mavromoustalkos, T.; Fytas, G.; Synthesis of 2-(2-adamantyl)piperidines and structure anti-influenza virus a activity relationship study using a combination of NMR spectroscopy and molecular modeling. Bioorg Med Chem Lett 1999, 9, 24, 3465. |
| 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) | 34016 | 2-pyridinyllithium | C5H4LiN | 详情 | 详情 | |
| (III) | 40405 | 2-(2-pyridinyl)-2-adamantanol | C15H19NO | 详情 | 详情 | |
| (IV) | 40406 | 2-(2-hydroxy-2-adamantyl)pyridinium chloride | C15H20ClNO | 详情 | 详情 | |
| (V) | 40407 | 2-(2-piperidinyl)-2-adamantanol | C15H25NO | 详情 | 详情 | |
| (VI) | 40408 | 2-(2-chloro-2-adamantyl)piperidinium chloride | C15H25Cl2N | 详情 | 详情 | |
| (VII) | 40409 | 2-tricyclo[3.3.1.1(3,7)]dec-2-ylidenepiperidine | C15H23N | 详情 | 详情 | |
| (VIII) | 40410 | 6-(2-adamantyl)-2,3,4,5-tetrahydropyridine | C15H23N | 详情 | 详情 |