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【结 构 式】 
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【药物名称】Atracurium besilate, Atracurium besylate, BW-33A, Nimbex, Tracrium 【化学名称】2-(2-Carboxyethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinolinium benzenesulfonate pentamethylene ester 【CA登记号】64228-81-5 【 分 子 式 】C65H82N2O18S2 【 分 子 量 】1243.50889 |
【开发单位】Abbott (Proprietary), GlaxoSmithKline (Originator) 【药理作用】Adjuncts to Anesthesia, ANALGESIC AND ANESTHETIC DRUGS, Neuromuscular Blockers |
合成路线1
The reaction of acryloyl chloride (I) with pentane-1,5-diol (II) by means of triethylamine and pyrogalol in hot benzene gives 1,5-pentamethylene diacrylate (III), which is condensed with tetrahydropapaverine (IV) in refluxing benzene to afford N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-bis(tetrahydropapaverine) (V). Finally, this compound is quaternized by treatment with methyl benzenesulfonate in acetonitrile.
| 【1】 Dewar, G.H.; Dhar, N.C.; Sternlake, J.B.; Urwin, R.J.; Waigh, R.D. (Glaxo Wellcome Inc.); Quarternary ammonium compounds. DE 2655883; FR 2334359; JP 52077069; US 4179507 . |
| 【2】 Serradell, M.N.; Blancafort, P.; Castaner, J.; Hillier, K.; Atracurium Besilate. Drugs Fut 1980, 5, 11, 541. |
| 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) | 11577 | Acryloyl chloride; Acrylyl chloride;2-Propenoyl chloride | 814-68-6 | C3H3ClO | 详情 | 详情 |
| (II) | 15471 | 1,5-pentanediol | 111-29-5 | C5H12O2 | 详情 | 详情 |
| (III) | 15470 | 5-(acryloyloxy)pentyl acrylate; 1,6-Hexanediol Diacrylate | 36840-85-4 | C11H16O4 | 详情 | 详情 |
| (IV) | 15468 | 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; 1-(3,4-dimethoxybenzyl)-6-methoxy-1,2,3,4-tetrahydro-7-isoquinolinyl methyl ether | C20H25NO4 | 详情 | 详情 | |
| (V) | 15473 | 5-([3-[(1R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]propanoyl]oxy)pentyl 3-[(1R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]propanoate | C51H66N2O12 | 详情 | 详情 | |
| (VI) | 15474 | methyl benzenesulfonate | 80-18-2 | C7H8O3S | 详情 | 详情 |