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【结 构 式】 
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【药物名称】 【化学名称】N-[1-[1-(Carbamoyl)cyclopentyl]-2-oxopyrrolidin-3(R)-yl]-L-prolylamide 【CA登记号】 【 分 子 式 】C15H24N4O3 【 分 子 量 】308.38353 |
【开发单位】McMaster University (Originator), University of Minnesota (Originator) 【药理作用】Antidepressants, Antiparkinsonian Drugs, Extrapyramidal Disorders, Treatment of, Mood Disorders, Treatment of, NEUROLOGIC DRUGS, PSYCHOPHARMACOLOGIC DRUGS |
合成路线1
This compound has been obtained by two related ways: 1) The reaction of 1-(tert-butoxycarbonylamino)cyclopentane-1-carboxylic acid (I) with ammonia, EDC and HOBT gives the amide (II), which is deprotected with 4N HCl and condensed with N-(tert-butoxycarbonyl)-D-methionine (III) by means of EDC and HOBT yielding the dipeptide (IV). The cyclization of (IV) with methyl iodide and NaH affords the pyrrolidinone (V), which is deprotected with HCl and condensed with 1-(benzyloxycarbonyl)-L-proline (VI) by means of EDC and HOBT giving the protected seudopeptide (VII). Finally, this compound is deprotected by hydrogenation with H2 over Pd/C. 2) The deprotection of (V) with HCl and its condensation with 1-(tert-butoxycarbonyl)-L-proline (VIII) by means of EDC and HOBT gives the protected seudopeptide (IX), which is finally deprotected with 4N HCl.
| 【1】 Evans, M.C.; et al.; Synthesis and dopamine receptor modulating activity of novel peptidomimetics of L-prolyl-L-leucyl-glycinamide featuring alpha,alpha-disubstituted amino acids. J Med Chem 1999, 42, 8, 1441. |
| 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) | 30890 | 1-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid | C11H19NO4 | 详情 | 详情 | |
| (II) | 30891 | tert-butyl 1-(aminocarbonyl)cyclopentylcarbamate | C11H20N2O3 | 详情 | 详情 | |
| (III) | 26710 | (2R)-2-[(tert-butoxycarbonyl)amino]-4-(methylsulfanyl)butyric acid | 5241-66-7 | C10H19NO4S | 详情 | 详情 |
| (IV) | 30892 | tert-butyl (1R)-1-([[1-(aminocarbonyl)cyclopentyl]amino]carbonyl)-3-(methylsulfanyl)propylcarbamate | C16H29N3O4S | 详情 | 详情 | |
| (V) | 30893 | tert-butyl (3R)-1-[1-(aminocarbonyl)cyclopentyl]-2-oxopyrrolidinylcarbamate | C15H25N3O4 | 详情 | 详情 | |
| (VI) | 19113 | (2S)-1-[(benzyloxy)carbonyl]-2-pyrrolidinecarboxylic acid | 1148-11-4 | C13H15NO4 | 详情 | 详情 |
| (VII) | 30894 | benzyl (2S)-2-[([(3R)-1-[1-(aminocarbonyl)cyclopentyl]-2-oxopyrrolidinyl]amino)carbonyl]-1-pyrrolidinecarboxylate | C23H30N4O5 | 详情 | 详情 | |
| (VIII) | 16734 | (2S)-1-(tert-butoxycarbonyl)tetrahydro-1H-pyrrole-2-carboxylic acid; N-alpha-t-BOC-L-proline; (2S)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid | C10H17NO4 | 详情 | 详情 | |
| (IX) | 30895 | tert-butyl (2S)-2-[([(3R)-1-[1-(aminocarbonyl)cyclopentyl]-2-oxopyrrolidinyl]amino)carbonyl]-1-pyrrolidinecarboxylate | C20H32N4O5 | 详情 | 详情 |