Abstract
The iridium(III)-catalyzed ortho-C-H amidation of benzoic acids with sulfonyl azides is described. These transformations allow the facile generation of N-sulfonyl anthranilic acids, which are known as crucial scaffolds found in biologically active molecules. In addition, all synthetic products were evaluated for in vitro anti-inflammatory activity against interleukin-1β (IL-1β) and cyclooxygenase-2 (COX-2) with lipopolysaccharide (LPS)-induced RAW264.7 cells. Notably, compounds 4c and 4d, generated from p-OMe- and p-Br-sulfonyl azides, were found to display potent anti-inflammatory property stronger than that of well-known NSAIDs ibuprofen.
Keywords:
Anthranilic acids; Anti-inflammatory; Benzoic acids; Iridium; Sulfonyl azides.
Copyright © 2017 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Anti-Inflammatory Agents / chemical synthesis*
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Anti-Inflammatory Agents / pharmacology
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Benzoates / chemistry*
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Catalysis
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Cyclooxygenase 2 / metabolism
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Interleukin-1beta / metabolism
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Iridium / chemistry*
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Lipopolysaccharides / toxicity
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Macrophages / drug effects
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Mice
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Nitrogen / chemistry
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RAW 264.7 Cells
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Sulfonamides / chemical synthesis*
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Sulfonamides / chemistry
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Sulfonamides / pharmacology
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ortho-Aminobenzoates / chemical synthesis
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ortho-Aminobenzoates / chemistry*
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ortho-Aminobenzoates / pharmacology
Substances
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2-(4-bromophenylsulfonamido)-6-methylbenzoic acid
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2-(4-methoxyphenylsulfonamido)-6-methylbenzoic acid
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Anti-Inflammatory Agents
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Benzoates
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Interleukin-1beta
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Lipopolysaccharides
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Sulfonamides
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ortho-Aminobenzoates
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Iridium
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Cyclooxygenase 2
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Nitrogen