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【结 构 式】 
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【药物名称】 【化学名称】2-(Ethylamino)-1-hexadecanol 【CA登记号】 【 分 子 式 】C18H39NO 【 分 子 量 】285.51763 |
【开发单位】Universidad de Salamanca (Originator), Universidad de Valencia (Originator) 【药理作用】Antiarthritic Drugs, ANTIINFECTIVE THERAPY, Antileishmanials, CARDIOVASCULAR DRUGS, GASTROINTESTINAL DRUGS, Pancreatic Disorders, Treatment of, Respiratory Distress Syndrome, Agents for, RESPIRATORY DRUGS, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Treatment of Protozoal Diseases, Treatment of Shock, Phospholipase A2 Inhibitors |
合成路线1
N-Boc-2-Aminohexadecanoic acid (I) was reduced to the Boc-aminoalcohol (III) via conversion to the mixed anhydride (II), which was subsequently reduced with NaBH4. Alcohol (III) was protected as the benzyl ether (IV) by alkylation with benzyl chloride in the presence of NaH. After acid deprotection of the N-Boc group of (IV), the resultant primary amine (V) was monoalkylated with ethyl bromide under controlled conditions to afford (VI). Finally, hydrogenolysis of the benzyl ether function of (VI) over Pd/C furnished the title amino alcohol.
| 【1】 del Olmo, E.; Alves, M.; Lopez, J.L.; Inchaustti, A.; Yaluff, G.; Rojas de Arias, A.; San Feliciano, A.; Leishmanicidal activity of some aliphatic diamines and amino-alcohols. Bioorg Med Chem Lett 2002, 12, 4, 659. |
| 【2】 Alves, M.; del Olmo, E.; Ubeda, A.; López, J.L.; San Feliciano, A.; Lucas, R.; Payá, M.; Synthesis and enzyme inhibitory activities of a series of lipidic diamine and aminoalcohol derivatives on cytosolic and secretory phospholipases A2. Bioorg Med Chem Lett 2000, 10, 3, 285. |
| 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) | 51342 | 2-[(tert-butoxycarbonyl)amino]hexadecanoic acid | C21H41NO4 | 详情 | 详情 | |
| (II) | 51343 | C24H45NO6 | 详情 | 详情 | ||
| (III) | 51344 | tert-butyl 1-(hydroxymethyl)pentadecylcarbamate | C21H43NO3 | 详情 | 详情 | |
| (IV) | 51345 | tert-butyl 1-[(benzyloxy)methyl]pentadecylcarbamate | C28H49NO3 | 详情 | 详情 | |
| (V) | 51346 | 1-(benzyloxy)-2-hexadecanamine; 1-[(benzyloxy)methyl]pentadecylamine | C23H41NO | 详情 | 详情 | |
| (VI) | 51347 | 1-(benzyloxy)-N-ethyl-2-hexadecanamine; N-[1-[(benzyloxy)methyl]pentadecyl]-N-ethylamine | C25H45NO | 详情 | 详情 |