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【结 构 式】 
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【药物名称】 【化学名称】(±)-cis-1-Hydroxy-6-methoxy-3,3,14-trimethyl-2-(4-pentenoyloxy)-2,3,7,14-tetrahydro-1H-benzo[b]pyrano[3,2-h]acridin-7-one 【CA登记号】 【 分 子 式 】C29H29NO6 【 分 子 量 】487.55758 |
【开发单位】CNRS (Originator), INSERM (Originator), Servier (Originator) 【药理作用】ONCOLYTIC DRUGS, DNA-Damaging Drugs |
合成路线1
Dihydroxylation of the benzo[b]pyrano[3,2-h]acridinone derivative (I) by means of N-methylmorpholine-N-oxide in the presence of OsO4 leads to the cis-diol (II), which upon esterification with 4-pentenoyl chloride in pyridine furnishes a mixture of diester (III) and the title mono-pentenoate ester, which can be separated employing flash chromatography.
| 【1】 Mai, H.D.T.; Gaslonde, T.; Michel, S.; Tillequin, F.; Koch, M.; Bongui, J.-B.; Elomri, A.; Seguin, E.; Pfeiffer, B.; Renard, P.; David-Cordonnier, M.-H.; Laine, W.; Bailly C.; Kraus-Berthier, L.; Leonce, S.; Hickman, J.A.; Pierre, A.; Structure-activity relationships and mechanism of action of antitumor benzo[b]pyrano[3,2-h]acridin-7-one acronycine analogues. J Med Chem 2003, 46, 14, 3072. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 61648 | 4-PENTENOYL CHLORIDE | C5H7ClO | 详情 | 详情 | ||
| (I) | 47435 | 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one | C24H21NO3 | 详情 | 详情 | |
| (II) | 47436 | (1S,2S)-1,2-dihydroxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one | C24H23NO5 | 详情 | 详情 | |
| (III) | 64870 | 3,3,14-trimethyl-6-(methyloxy)-7-oxo-1-(4-pentenoyloxy)-2,3,7,14-tetrahydro-1H-benzo[b]pyrano[3,2-h]acridin-2-yl 4-pentenoate | C34H35NO7 | 详情 | 详情 |