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【结 构 式】 
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【药物名称】Chandonium iodide, Candocuronium iodide, HS-310 【化学名称】17a,17a-Dimethyl-3beta-(1-methylpyrrolidinio)-17a-azonia-17a-homoandrost-5-ene diiodide 【CA登记号】54278-85-2 【 分 子 式 】C26H46I2N2 【 分 子 量 】640.47872 |
【开发单位】Central Drug Research Institute (Originator), Panjab University (Originator) 【药理作用】Adjuncts to Anesthesia, ANALGESIC AND ANESTHETIC DRUGS, Neuromuscular Blockers |
合成路线1
Dehydroepiandrosterone acetate (I) is converted to the lactam (II), which is hydrolyzed to the alcohol (III). Oppenauer oxidation of (III) gives the a,3-unsaturated ketone (IV). The intermediate (IV) is treated with pyrrolidine in methanol to give the enamine (V) in excellent yield. The latter, on sodium borohydride reduction affords (VI), the 3beta- configuration being assigned on the basis of similar reductions reported elsewhere. Sodium and n-pentanol reduction of (VI) leads to the diamine (VII), the methyl derivative (VIII) of which is prepared and converted into the dimethiodide (HS-310).
| 【1】 Singh, H.; Paul, D.; Steroids and related studies. Part XXV. Chandonium iodide (17alpha-Methyl-3beta-pyrrolidino-17alpha-aza-D-homoandrost-5-ene-Dimethyliodide) and other quaternary ammonium steroid analogues. J Chem Soc - Perkins Trans I 1974, 1476. |
| 【2】 Schmitt, J.; et al.; Recherches sur les amino-stéroïdes. VI. Stéroïdes à restes aminés fixés en C3. Préparation par réduction au borohydrurre de sodium et au diborane des "énamines" derivées de céto-3. Bull Soc Chim France 1963, 807-815. |
| 【3】 Marshall, J.A.; Johnson, W.S.; Reduction od steroidal enamines. J Org Chem 1963, 28, 421-423. |
| 【4】 Arya. V.P.; Chandonium iodide. Drugs Fut 1978, 3, 11, 807. |
| 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) | 20083 | Prasterone acetate;3b-Hydroxy-5-androstene-17-one acetate；Dehydroisoandrosterone acetate;Dehydroepiandrosterone 3-acetate;Dehydroepiandrosterone acetate;(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | 853-23-6 | C21H30O3 | 详情 | 详情 |
| (II) | 39912 | (4aS,4bR,8S,10aR,10bS,12aS)-10a,12a-dimethyl-2-oxo-1,2,3,4,4a,4b,5,7,8,9,10,10a,10b,11,12,12a-hexadecahydronaphtho[2,1-f]quinolin-8-yl acetate | C21H31NO3 | 详情 | 详情 | |
| (III) | 39913 | (4aS,4bR,8S,10aR,10bS,12aS)-8-hydroxy-10a,12a-dimethyl-3,4,4a,4b,5,7,8,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinolin-2(1H)-one | C19H29NO2 | 详情 | 详情 | |
| (IV) | 39914 | (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-1,3,4,4a,4b,5,6,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinoline-2,8-dione | C19H27NO2 | 详情 | 详情 | |
| (V) | 11376 | Pyrrolidine | 123-75-1 | C4H9N | 详情 | 详情 |
| (VI) | 39915 | (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-8-(1-pyrrolidinyl)-3,4,4a,4b,5,9,10,10a,10b,11,12,12a-dodecahydronaphtho[2,1-f]quinolin-2(1H)-one | C23H34N2O | 详情 | 详情 | |
| (VII) | 39916 | (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-8-(1-pyrrolidinyl)-3,4,4a,4b,5,7,8,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinolin-2(1H)-one | C23H36N2O | 详情 | 详情 | |
| (VIII) | 39917 | (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-8-(1-pyrrolidinyl)-1,2,3,4,4a,4b,5,7,8,9,10,10a,10b,11,12,12a-hexadecahydronaphtho[2,1-f]quinoline | C23H38N2 | 详情 | 详情 | |
| (IX) | 39918 | (4aS,4bR,10aR,10bS,12aS)-1,10a,12a-trimethyl-8-(1-pyrrolidinyl)-1,2,3,4,4a,4b,5,7,8,9,10,10a,10b,11,12,12a-hexadecahydronaphtho[2,1-f]quinoline | C24H40N2 | 详情 | 详情 |