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【结 构 式】 
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【药物名称】ML-3176 【化学名称】1-[2-[4-(Carboxymethyl)phenoxy]ethyl]-3-(1-dodecanoyl)-1H-indole-2-carboxylic acid 【CA登记号】192182-47-1 【 分 子 式 】C31H39NO6 【 分 子 量 】521.65958 |
【开发单位】Merckle (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, RESPIRATORY DRUGS, Non-Steroidal Antiinflammatory Drugs, Phospholipase A2 Inhibitors |
合成路线1
The condensation of ethyl indole-2-carboxylate (I) with dodecanoic acid (II) in the presence of polyphosphoric acid and trifluoroacetic anhydride produced the corresponding 3-dodecanoylindole (III). Subsequent alkylation of (III) with ethyl 4-(2-bromoethoxy)phenylacetate (IV) using potassium tert-butoxide in DMSO afforded the N-alkylated indole (V). The ethyl ester groups of (V) were finally hydrolyzed with KOH to provide the target diacid compound.
| 【1】 Lehr, M. (Merckle GmbH); Acylpyrroldicarboxylic acids and acylindoldicarboxylic acids and their derivs. and inhibitors of the cytosolic phospholipase A2. EP 0923546; WO 9805637 . |
| 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) | 27783 | Indole-2-carboxylic acid ethyl ester; 2-Carbethoxyindole; 1H-indole-2-carboxylic acid ethyl ester | 3770-50-1 | C11H11NO2 | 详情 | 详情 |
| (II) | 30803 | lauric acid | 143-07-7 | C12H24O2 | 详情 | 详情 |
| (III) | 30804 | ethyl 3-dodecanoyl-1H-indole-2-carboxylate | C23H33NO3 | 详情 | 详情 | |
| (IV) | 30805 | ethyl 2-[4-(2-bromoethoxy)phenyl]acetate | C12H15BrO3 | 详情 | 详情 | |
| (V) | 30806 | ethyl 3-dodecanoyl-1-[2-[4-(2-ethoxy-2-oxoethyl)phenoxy]ethyl]-1H-indole-2-carboxylate | C35H47NO6 | 详情 | 详情 |