【结 构 式】 |
【药物名称】Flavoneacetic acid, Mitoflaxone, CRC-85/31, LM-975, FAA, NSC-347512 【化学名称】4-Oxo-2-phenyl-4H-1-benzopyran-8-acetic acid 【CA登记号】87626-55-9 【 分 子 式 】C17H12O4 【 分 子 量 】280.28279 |
【开发单位】Lipha (Originator) 【药理作用】Oncolytic Drugs |
合成路线1
Treatment of 8-bromomethyl-2-phenylflavone (I) with KCN in EtOH-H2O for 3 h gives the nitrile intermediate (II) (m.p. 165-7 C) in 67% yield, which in diluted acetic-sulfuric acid is hydrolyzed to flavoneacetic acid (III) in 88% yield. On refluxing the potassium salt of the acid with 2-diethylaminoethyl chloride in acetone for 4 h, followed by converting the resulting ester to the hydrochloride salt, the diethylaminoethyl ester of flavoneacetic acid (m.p. 186 C) is produced in 70% yield.
【1】 Briet, P.; Berthelon, J.J.; Collonges, F.; Atassi, G.; Synthesis and antitumor activity of some 8-substit. Eur J Med Chem 1985, 20, 393. |
【2】 Berthelon, J.-J.; Collonges, F.; Briet, P. (Lipha Santé); 8-Haloalkyl-4H-(1)-benzopyran-4-ones and preparati. EP 0080419 . |
【3】 Berthelon, J.-J.; Collonges, F.; Briet, P. (Lipha Santé); (Oxo-4-4H-(1)-benzopyran-8-yl) alkanoic acids, sal. EP 0080934; US 4602034 . |
【4】 Berthelon, J.-J.; Collonges, F.; Briet, P. (Lipha Santé); 8-Haloalkyl-4H-1-benzopyran-4-ones and methods of . FR 2536396 . |
【5】 Cheng, C.C.; Zee-Cheng, R.K.-Y.; Flavoneacetic acid. Drugs Fut 1987, 12, 2, 123. |
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) | 22859 | 8-(bromomethyl)-2-phenyl-4H-chromen-4-one | C16H11BrO2 | 详情 | 详情 | |
(II) | 22860 | 2-(4-oxo-2-phenyl-4H-chromen-8-yl)acetonitrile | C17H11NO2 | 详情 | 详情 | |
(III) | 22861 | 2-(4-oxo-2-phenyl-4H-chromen-8-yl)acetic acid | C17H12O4 | 详情 | 详情 | |
(IV) | 16194 | 2-chloro-N,N-diethyl-1-ethanamine; N-(2-chloroethyl)-N,N-diethylamine | 100-35-6 | C6H14ClN | 详情 | 详情 |
Extended Information