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【结 构 式】 
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【分子编号】10817 【品名】(4S)-4,11-Diethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 7-Ethylcamptothecin 【CA登记号】 |
【 分 子 式 】C22H20N2O4 【 分 子 量 】376.41188 【元素组成】C 70.2% H 5.36% N 7.44% O 17% |
合成路线1
该中间体在本合成路线中的序号：(II)A more complete synthesis for CPT-11 has been reported: The reaction of camptothecin (I) with propionaldehyde and FeSO4 in water gives 7-ethylcamptothecin (II), which is oxidized with H2O2 in hot acetic acid yielding 7-ethylcamptothecin 1-oxide (III). The isomerization of (III) with UV light (high-pressure Hg lamp) in dioxane-1 N H2SO4 affords 7-ethyl-10-hydroxycamptothecin (IV), which is treated with phosgene and triethylamine in dioxane to give the corresponding chlorocarbonyl derivative (V). Finally, this compound is condensed with 4-piperidinopiperidine (VI) by means of pyridine in dichloromethane.
| 【1】 Nokata, K.-I.; Furuta, T.; Yokokura, T.; Okajima, S.; Sawada, S.; Sugino, E.; Miyasaka, T.; Aiyama, R.; Yamaguchi, K.; Synthesis and antitumor activity of 20(S)-camptothecin derivatives: Carbamate-linked, water-soluble derivatives of 7-ethyl-10-hydroxycamptothecin. Chem Pharm Bull 1991, 39, 6, 1446-54. |
| 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) | 10816 | Camptothecin; (4S)-4-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 4-et-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo(b,h)fluorene-3,13-dione | 7689-03-4 | C20H16N2O4 | 详情 | 详情 |
| (II) | 10817 | (4S)-4,11-Diethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 7-Ethylcamptothecin | C22H20N2O4 | 详情 | 详情 | |
| (III) | 10818 | (4S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-6-ium-6-olate; 7-Ethylcamptothecin 1-oxide | C22H20N2O5 | 详情 | 详情 | |
| (IV) | 10819 | (4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 7-Ethyl-10-hydroxycamptothecin | C22H20N2O5 | 详情 | 详情 | |
| (V) | 10820 | (4S)-9-[(Chlorocarbonyl)oxy]-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline | C23H19ClN2O6 | 详情 | 详情 | |
| (VI) | 10821 | 4-Piperidinopiperidine | 4897-50-1 | C10H20N2 | 详情 | 详情 |