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【结 构 式】 
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【药物名称】PST-2107 【化学名称】17beta-(3-Furyl)-3beta-(2-guanidinoethoxy)-5beta-androstan-14beta-ol nitrate 【CA登记号】 【 分 子 式 】C26H42N4O6 【 分 子 量 】506.64784 |
【开发单位】Sigma-Tau (Originator) 【药理作用】CARDIOVASCULAR DRUGS, Heart Failure Therapy, Hypertension, Treatment of, Positive Inotropic Agents, Na+/K+-ATPase Inhibitors |
合成路线1
Reaction of furylandrostanediol (I) (J Chem Soc (C) 1966, 377) with bromoacetaldehyde diethylacetal (II) in the presence of NaH in refluxing tetahydrofuran provided ether (III). Subsequent acid hydrolysis of ethyl acetal of (III) gave aldehyde (IV), which was reduced to alcohol (V) with NaBH4. Coupling of (V) with phthalimide (VI) under Mitsunobu conditions produced the N-alkylated phthalimide (VII), and further hydrazinolysis yielded primary amine (VIII). The required guanidine function was finally introduced by treatment of (VIII) with 3,5-dimethyl-1-pyrazolylformamidinium nitrate (IX) in boiling EtOH.
| 【1】 Quadri, L.; Bernardi, L.; Ferrari, P.; Gobbini, M.; Melloni, P.; Valentino, L. (Sigma-Tau Industrie Farmaceutiche Riunite SpA); Cyclopentanperhydrophenanthren-17beta-(3-furyl)-3-derivs. and pharmaceutical compsns. comprising same for the treatment of cardiovascular disorders. EP 0576915; JP 1994065284; US 5432169 . |
| 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) | 27462 | (3S,5R,8R,9S,10S,13R,17R)-17-(3-furyl)-10,13-dimethylhexadecahydro-14H-cyclopenta[a]phenanthrene-3,14-diol | C23H34O3 | 详情 | 详情 | |
| (II) | 12113 | 2-Bromo-1-ethoxyethyl ethyl ether; 2-Bromo-1,1-diethoxyethane; Bromoacetaldehyde diethylacetal | 2032-35-1 | C6H13BrO2 | 详情 | 详情 |
| (III) | 27463 | (3S,5R,8R,9S,10S,13R,17R)-3-(2,2-diethoxyethoxy)-17-(3-furyl)-10,13-dimethylhexadecahydro-14H-cyclopenta[a]phenanthren-14-ol | C29H46O5 | 详情 | 详情 | |
| (IV) | 27464 | 2-[[(3S,5R,8R,9S,10S,13R,14S,17R)-17-(3-furyl)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]acetaldehyde | C25H36O4 | 详情 | 详情 | |
| (V) | 27465 | (3S,5R,8R,9S,10S,13R,17R)-17-(3-furyl)-3-(2-hydroxyethoxy)-10,13-dimethylhexadecahydro-14H-cyclopenta[a]phenanthren-14-ol | C25H38O4 | 详情 | 详情 | |
| (VI) | 12376 | Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione | 85-41-6 | C8H5NO2 | 详情 | 详情 |
| (VII) | 27466 | 2-(2-[[(3S,5R,8R,9S,10S,13R,14S,17R)-17-(3-furyl)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]ethyl)-1H-isoindole-1,3(2H)-dione | C33H41NO5 | 详情 | 详情 | |
| (VIII) | 27467 | (3S,5R,8R,9S,10S,13R,17R)-3-(2-aminoethoxy)-17-(3-furyl)-10,13-dimethylhexadecahydro-14H-cyclopenta[a]phenanthren-14-ol | C25H39NO3 | 详情 | 详情 | |
| (IX) | 10268 | 3,5-Dimethyl-1H-pyrazole-1-carboximidamide | C6H10N4 | 详情 | 详情 |