1. Synthesis and anti-inflammatory evaluation of N -sulfonyl anthranilic acids via Ir(III)-catalyzed C–H amidation of benzoic acids
- Author
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Byung Mu Lee, Hyo Sun Suh, Sang Hoon Han, Sangil Han, Hyung Sik Kim, Yongguk Oh, Young Hoon Jung, Hyeim Jo, Neeraj Kumar Mishra, and In Su Kim
- Subjects
Lipopolysaccharides ,Lipopolysaccharide ,Nitrogen ,Stereochemistry ,medicine.drug_class ,Interleukin-1beta ,Clinical Biochemistry ,Anti-Inflammatory Agents ,Pharmaceutical Science ,chemistry.chemical_element ,Iridium ,010402 general chemistry ,Benzoates ,01 natural sciences ,Biochemistry ,Catalysis ,Anti-inflammatory ,Mice ,chemistry.chemical_compound ,Drug Discovery ,medicine ,Animals ,Molecule ,ortho-Aminobenzoates ,Molecular Biology ,Sulfonyl ,chemistry.chemical_classification ,Sulfonamides ,010405 organic chemistry ,Chemistry ,Macrophages ,Organic Chemistry ,Biological activity ,In vitro ,0104 chemical sciences ,RAW 264.7 Cells ,Cyclooxygenase 2 ,Molecular Medicine - 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.
- Published
- 2017
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