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【结 构 式】 
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【药物名称】 【化学名称】3-Methyl-7-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-benzopyran-2-one hydrochloride 【CA登记号】 【 分 子 式 】C23H27ClN2O3 【 分 子 量 】414.93624 |
【开发单位】AstraZeneca (Originator) 【药理作用】Drugs Acting on 5-Hydroxytryptamine Receptors, Drugs Acting on Dopamine Receptors |
合成路线1
7-Hydroxy-3-methylcoumarin (III) was obtained by Perkin reaction of 2,4-dihydroxybenzaldehyde (I) and propionic anhydride (II) in the presence of sodium propionate in pyridine. Alkylation of N-phenylpiperazine (IV) with 1-bromo-3-chloropropane (V) and NaOH in acetone provided the chloropropyl compond (VI), which was finally condensed with coumarin (III) using NaH in DMF.
| 【1】 Antonello, C.; et al.; Synthesis and characterization of new methylpsoralens as potential photochemotherapeutic agents. Farmaco 1994, 49, 4, 277. |
| 【2】 Teran, C.; Santana, L.; Uriarte, E.; Fall, Y.; Unelius, L.; Tolf, B.R.; Phenylpiperazine derivatives with strong affinity for 5HT1A, D2A and D3 receptors. Bioorg Med Chem Lett 1998, 8, 24, 3567. |
| 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) | 20094 | 2,4-dihydroxybenzaldehyde | 95-01-2 | C7H6O3 | 详情 | 详情 |
| (II) | 20095 | propionic anhydride | 123-62-6 | C6H10O3 | 详情 | 详情 |
| (III) | 20096 | 7-hydroxy-3-methyl-2H-chromen-2-one | C10H8O3 | 详情 | 详情 | |
| (IV) | 10756 | N-Phenylpiperazine; 1-Phenylpiperazine; Phenyl piperazine | 92-54-6 | C10H14N2 | 详情 | 详情 |
| (V) | 10358 | 1-Bromo-3-chloropropane | 109-70-6 | C3H6BrCl | 详情 | 详情 |
| (VI) | 20099 | 1-(3-chloropropyl)-4-phenylpiperazine | C13H19ClN2 | 详情 | 详情 |
Extended Information