Efficient synthesis of [6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl]-acetic acid, a novel COX-2 inhibitor
Efficient synthesis of [6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl]-acetic acid, a novel COX-2 inhibitor
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DOI：
10.1021/jo034274r
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发表时间：
2003-05-16
影响因子：
3.6
通讯作者：
Murata, Y
中科院分区：
文献类型：
--
作者：
Caron, S;Vazquez, E;Murata, Y
本文报道了选择性环氧合酶2（考克斯-2）抑制剂6-氯-2-（4-氯苯甲酰基）-1H-吲哚-3-乙酸（1）的合成。该合成依赖于一种新的吲哚形成，涉及烷基化/1，4-加成/消除/异构化级联反应。证明了从磺酰胺13和溴酮14到所需吲哚（1）的整个序列可以在一锅中进行。
The synthesis of 6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-ylacetic acid (1), a selective cyclooxygenase 2 (COX-2) inhibitor, is described. The synthesis relied on a novel indole formation that involved an alkylation/1,4-addition/ elimination/isomerization cascade. It was demonstrated that the entire sequence from sulfonamide 13 and bromoketone 14 to the desired indole (1) could be executed in a single pot.