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【结 构 式】 
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【药物名称】BKM-570 【化学名称】O-(2,6-Dichlorobenzyl)-N2-[3-(pentafluorophenyl)-2-propenoyl]-N1-(2,2,6,6-tetramethylpiperidin-4-yl)-L-tyrosinamide 【CA登记号】259885-54-6, 259886-28-7 (hydrochloride), 259886-27-6 (trifluoroacetate) 【 分 子 式 】C34H34Cl2F5N3O3 【 分 子 量 】698.56638 |
【开发单位】University of Colorado (Originator) 【药理作用】ONCOLYTIC DRUGS, Bradykinin Receptor Antagonists |
合成路线1
N-Boc-O-(2,6-Dichlorobenzyl)-L-tyrosine (I) is coupled to 4-amino-2,2,6,6-tetramethylpiperidine (II) using BOP in DMF to provide amide (III). The N-Boc protecting group of (III) is then removed by trifluoroacetic acid, yielding amine (IV). This is finally acylated with pentafluorocinnamic acid (V) in the presence of BOP/i-Pr2NEt to furnish the title compound (1,2).
| 【1】 Stewart, J.M.; et al.; Bradykinin-related compounds as new drugs for cancer and inflammation. Can J Physiol Pharmacol 2002, 80, 4, 275. |
| 【2】 Stewart, J.M.; Gera, L.; Chan, D.C.F.; York, E.; Bunn, P.; Anti-cancer cpds. and methods related thereto. WO 0011022 . |
| 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) | 64526 | (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(2,6-dichlorobenzyl)oxy]phenyl}propanoic acid | C21H23Cl2NO5 | 详情 | 详情 | |
| (II) | 25596 | 2,2,6,6-tetramethyl-4-piperidinamine | 36768-62-4 | C9H20N2 | 详情 | 详情 |
| (III) | 64527 | tert-butyl (1S)-1-{4-[(2,6-dichlorobenzyl)oxy]benzyl}-2-oxo-2-[(2,2,6,6-tetramethyl-4-piperidinyl)amino]ethylcarbamate | C30H41Cl2N3O4 | 详情 | 详情 | |
| (IV) | 64528 | (2S)-2-amino-3-{4-[(2,6-dichlorobenzyl)oxy]phenyl}-N-(2,2,6,6-tetramethyl-4-piperidinyl)propanamide | C25H33Cl2N3O2 | 详情 | 详情 | |
| (V) | 64529 | (E)-3-(2,3,4,5,6-pentafluorophenyl)-2-propenoic acid | C9H3F5O2 | 详情 | 详情 |
Extended Information