|
【结 构 式】 
|
【药物名称】PD-188669 【化学名称】4-Benzyl-1-[4-(4-imidazolyl)-3-butynyl]piperidine 【CA登记号】 【 分 子 式 】C19H23N3 【 分 子 量 】293.41526 |
【开发单位】CoCensys (Originator), Pfizer (Originator) 【药理作用】Antiparkinsonian Drugs, Extrapyramidal Disorders, Treatment of, NEUROLOGIC DRUGS, NMDA Antagonists |
合成路线1
Coupling of 3-butyn-1-ol (I) with 4-iodo-1-phenylsulfonylimidazole (II) in the presence of CuI and Pd(PPh3)4 afforded the imidazolylbutynol (III), which was activated as the tosylate (IV) with p-toluenesulfonyl chloride in pyridine. Subsequent displacement of the tosylate group of (IV) by 4-benzylpiperidine (V) using NaHCO3 in hot DMF produced the corresponding N-(imidazolylbutynyl)piperidine with simultaneous cleavage of the benzenesulfonyl protecting group.
| 【1】 Serpa, K.A.; Wise, L.D.; Meltzer, L.T.; Gregory, T.F.; Wright, J.L.; Boxer, P.A.; Discovery of subtype-selective NMDA receptor ligands: 4-benzyl-1-piperidinylalkynylpyrroles, pyrazoles and imidazoles as NR1A/2B antagonists. Bioorg Med Chem Lett 1999, 9, 19, 2815. |
| 【2】 Boxer, P.A.; Woodward, R.M.; Meltzer, L.T.; D'Wise, L.; Gregory, T.F.; Novel series of 4-benzyl-N-(4-imidazole-1-alkynyl)piperidines as potent subtype selective NMDA receptor antagonists. 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 94. |
| 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) | 32507 | 3-butyn-1-ol | 927-74-2 | C4H6O | 详情 | 详情 |
| (II) | 32508 | 4-iodo-1-(phenylsulfonyl)-1H-imidazole | C9H7IN2O2S | 详情 | 详情 | |
| (III) | 32509 | 4-[1-(phenylsulfonyl)-1H-imidazol-4-yl]-3-butyn-1-ol | C13H12N2O3S | 详情 | 详情 | |
| (IV) | 32510 | 4-[1-(phenylsulfonyl)-1H-imidazol-4-yl]-3-butynyl 4-methylbenzenesulfonate | C20H18N2O5S2 | 详情 | 详情 | |
| (V) | 26225 | 4-benzylpiperidine | 31252-42-3 | C12H17N | 详情 | 详情 |
Extended Information