|
【结 构 式】 
|
【药物名称】 【化学名称】2-[2,4-Bis(4-methoxybenzoyl)-1H-pyrrol-1-yl]acetic acid 【CA登记号】 【 分 子 式 】C22H19NO6 【 分 子 量 】393.39983 |
【开发单位】Aristotle University of Thessaloniki (Originator) 【药理作用】ENDOCRINE DRUGS, Symptomatic Antidiabetic Agents, Treatment of Diabetic Complications, AGE Inhibitors (Maillard's Reaction Inhibitors), Aldose Reductase Inhibitors |
合成路线1
Friedel-Crafts acylation of 3-(p-methoxybenzoyl)pyrrole (I) with p-methoxybenzoyl chloride (II) gives rise to diketone (III). Subsequent alkylation of pyrrole (III) with ethyl bromoacetate (IV) in the presence of NaH and tris[(2-methoxyethoxy)ethyl]amine (TDA) furnishes the pyrrolylacetate (V). Finally, saponification of the ethyl ester group of (V) affords the target carboxylic acid.
| 【1】 Nicolaou, I.; Demopoulos, V.J.; Substituted pyrrol-1-ylacetic acids that combine aldose reductase enzyme inhibitory activity and ability to prevent the nonenzymatic irreversible modification of proteins from monosaccharides. J Med Chem 2003, 46, 3, 417. |
| 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) | 64031 | [4-(methyloxy)phenyl](1H-pyrrol-3-yl)methanone | C12H11NO2 | 详情 | 详情 | |
| (II) | 22071 | 2-[1,2-bis[[(E)-(2,6-dichloro-4-methoxyphenyl)methylidene]amino]-2-(2-hydroxyphenyl)ethyl]phenol | C30H24Cl4N2O4 | 详情 | 详情 | |
| (III) | 64032 | [5-(4-methoxybenzoyl)-1H-pyrrol-3-yl](4-methoxyphenyl)methanone | C20H17NO4 | 详情 | 详情 | |
| (IV) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (V) | 64033 | ethyl 2-(2,4-bis{[4-(methyloxy)phenyl]carbonyl}-1H-pyrrol-1-yl)acetate | C24H23NO6 | 详情 | 详情 |
Extended Information