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【结 构 式】 
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【药物名称】BN-81674 【化学名称】1,1-Dipentyl-3(R)-(4-phenyl-1H-imidazol-2-yl)-2,3,4,9-tetrahydro-1H-beta-carboline 【CA登记号】252278-73-2 【 分 子 式 】C30H38N4 【 分 子 量 】454.66416 |
【开发单位】Institut Henri Beaufour (Originator) 【药理作用】PHARMACOLOGICAL TOOLS, Somatostatin srif1C (sst3) Antagonists |
合成路线1
Phenacyl ester (III) was prepared by treatment of the cesium salt of N-Boc-tryptophan (I) with 2-bromoacetophenone (II) in DMF. Cyclization of keto ester (III) with ammonium acetate in refluxing xylene yielded the target imidazole (IV). Acidic Boc group deprotection of (IV) then gave amine (V). Finally, Pictet-Spengler cyclization of (V) with 6-undecanone (VI) provided the desired tetrahydrocarboline.
| 【1】 Poitout, L.; et al.; Identification of potent non-peptide somatostatin antagonists with sst3 selectivity. J Med Chem 2001, 44, 18, 2990. |
| 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) | 16114 | N-alpha-t-BOC-L-tryptophan; (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propionic acid | 13139-14-5 | C16H20N2O4 | 详情 | 详情 |
| (II) | 10315 | 2-Bromo-1-phenyl-ethanone; 2-Bromo-1-phenyl-1-ethanone | 70-11-1 | C8H7BrO | 详情 | 详情 |
| (III) | 50501 | 2-oxo-2-phenylethyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoate | C24H26N2O5 | 详情 | 详情 | |
| (IV) | 50502 | tert-butyl (1R)-2-(1H-indol-3-yl)-1-(4-phenyl-1H-imidazol-2-yl)ethylcarbamate | C24H26N4O2 | 详情 | 详情 | |
| (V) | 50503 | (1R)-2-(1H-indol-3-yl)-1-(4-phenyl-1H-imidazol-2-yl)-1-ethanamine; (1R)-2-(1H-indol-3-yl)-1-(4-phenyl-1H-imidazol-2-yl)ethylamine | C19H18N4 | 详情 | 详情 | |
| (VI) | 50504 | 6-Hendecanone; 6-Undecanone; Di-n-amyl ketone; Diamyl ketone | 927-49-1 | C11H22O | 详情 | 详情 |