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【结 构 式】 
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【药物名称】 【化学名称】N-[4-(3,20-Dioxopregn-4-en-7alpha-ylsulfanyl)phenyl]-N'-[1(R)-phenylethyl]urea 【CA登记号】 【 分 子 式 】C36H44N2O3S 【 分 子 量 】584.82768 |
【开发单位】Georgetown University (Originator) 【药理作用】Modulators of the Therapeutic Activity of Antineoplastic Agents, Multidrug Resistance Modulators, ONCOLYTIC DRUGS, P-Glycoprotein (MDR-1) Inhibitors |
合成路线1
Progesterone (I) was oxidized to the 6-dehydro derivative (II) using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Conjugate addition of 4-aminothiophenol (III) to dienone (II) furnished the aminophenyl sulfide (IV). The target urea was then obtained by coupling of the amino compound (IV) with (R)-alpha-methylbenzyl isocyanate (V).
| 【1】 Clarke, R.; Leonessa, F.; Ghiorghis, A.; Kulawiec, R.J.; Talebian, A.; Kim, J.-H.; Hammer, C.; C-7 analogues of progesterone as potent inhibitors of the P-glycoprotein efflux pump. J Med Chem 2002, 45, 2, 390. |
| 【2】 Clarke, R.; Talebian, A.H.; Ghiorghis, A.; Leonessa, F.; Hammer, C. (Georgetown University); Progesterone analogs to reverse multidrug resistance. WO 9700683 . |
| 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) | 55957 | (9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one; (S)-Pregn-4-en-3,20-dione; 3,20-pregnene-4; 4-Pregnene-3,20-dione; beta-progesterone; Corlutin; Corlutina; Corluvite; Corporin; Corpus luteum hormone; Flavolutan; Fologenon; Gestone; Gestormone; Glanducorpin; Homoflaveine; Hormoluton; Lipolutin; Lucorteum; Luteal hormone; Lutein; Luteinique; Luteodyn; Luteogan; Luteohormone; Luteol; Luteosan; Luteostab; Luteovis; Lutex; Lutidon; Lutocyclin; Lutocylin; Lutocylol; Lutoform; Lutogyl; Lutren; Lutromone; Piaponon; Pranone; Pregn-4-ene-3,20-dione; pregnendione; Pregnene-3,20-dione; Pregnenedione; Primolut; Progekan; Progesterol; Progesterone; Progesteronum; Progestone; Prolidon; Syntolutan | 57-83-0 | C21H30O2 | 详情 | 详情 |
| (II) | 55958 | (9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | 1162-56-7 | C21H28O2 | 详情 | 详情 |
| (III) | 16490 | 4-aminophenylhydrosulfide; 4-aminothiophenol; 4-aminobenzenethiol | 1193-02-8 | C6H7NS | 详情 | 详情 |
| (IV) | 55959 | (7R,9S,10R,13S,14S,17S)-17-acetyl-7-[(4-aminophenyl)sulfanyl]-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one | C27H35NO2S | 详情 | 详情 | |
| (V) | 30212 | 1-[(1R)-1-isocyanatoethyl]benzene; (1R)-1-phenylethyl isocyanate | 33375-06-3 | C9H9NO | 详情 | 详情 |
Extended Information