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【结 构 式】 
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【药物名称】NCS-706 【化学名称】2-Iodo-9-(2-methoxybenzyl)-N6-methyladenine hydrochloride 【CA登记号】396653-34-2 【 分 子 式 】C14H15ClIN5O 【 分 子 量 】431.66595 |
【开发单位】CNRS (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, RESPIRATORY DRUGS, Phosphodiesterase IV Inhibitors, TNF-alpha Production Inhibitors |
合成路线1
Alkylation of 2-amino-6-chloropurine (I) with 2-methoxybenzyl chloride (II) in the presence of K2CO3 and Bu4NI gives the 9-substituted purine (III). Amino purine (III) is converted into the corresponding 2-iodo derivative (IV) by treatment with isoamyl nitrite in hot diiodomethane. Finally, displacement of the 6-chloro group of (IV) with methylamine furnishes the desired adenine derivative.
| 【1】 Raboisson, P.; Lugnier, C.; Muller, C.; Reimund, J.-M.; Schultz, D.; Pinna, G.; Le Bec, A.; Basaran, H.; Desaubry, L.; Gaudiot, F.; Seloum, M.; Bourguignon, J.-J.; Design, synthesis and structure-activity relationships of a series of 9-substituted adenine derivatives as selective phosphodiesterase type-4 inhibitors. Eur J Med Chem 2003, 38, 2, 199. |
| 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) | 11644 | 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine | 10310-21-1 | C5H4ClN5 | 详情 | 详情 |
| (II) | 31017 | 2-(chloromethyl)phenyl methyl ether; 1-(chloromethyl)-2-methoxybenzene | 7035-02-1 | C8H9ClO | 详情 | 详情 |
| (III) | 64982 | 6-chloro-9-{[2-(methyloxy)phenyl]methyl}-9H-purin-2-amine; 6-chloro-9-{[2-(methyloxy)phenyl]methyl}-9H-purin-2-ylamine | C13H12ClN5O | 详情 | 详情 | |
| (IV) | 64983 | 2-[(6-chloro-2-iodo-9H-purin-9-yl)methyl]phenyl methyl ether; 6-chloro-2-iodo-9-{[2-(methyloxy)phenyl]methyl}-9H-purine | C13H10ClIN4O | 详情 | 详情 |
Extended Information