Abstract
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.
MeSH terms
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Alkylation
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Catalysis
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Chlorobenzoates / chemical synthesis*
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Chlorobenzoates / pharmacology
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Combinatorial Chemistry Techniques*
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Cyclooxygenase 2
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / pharmacology
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Indicators and Reagents
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Indoleacetic Acids / chemical synthesis*
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Indoleacetic Acids / pharmacology
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Isoenzymes / antagonists & inhibitors*
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Molecular Structure
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Prostaglandin-Endoperoxide Synthases
Substances
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(6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl)acetic acid
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Chlorobenzoates
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Enzyme Inhibitors
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Indicators and Reagents
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Indoleacetic Acids
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Isoenzymes
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Cyclooxygenase 2
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Prostaglandin-Endoperoxide Synthases