Synthesis and anti-inflammatory evaluation of N-sulfonyl anthranilic acids via Ir(III)-catalyzed C–H amidation of benzoic acids. Issue 10 (15th May 2017)

• Record Type: Journal Article
• Authors: Han, Sang Hoon; Suh, Hyo Sun; Jo, Hyeim; Oh, Yongguk; Mishra, Neeraj Kumar; Han, Sangil; Kim, Hyung Sik; Jung, Young Hoon; Lee, Byung Mu; Kim, In Su
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 27:Issue 10(2017)
• Page Start: 2129
• Page End: 2134
• Publication Date: 2017-05-15
• Subjects: Anthranilic acids -- Anti-inflammatory -- Benzoic acids -- Sulfonyl azides -- Iridium; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2017.03.072
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: The iridium(III)-catalyzed ortho -C–H amidation of benzoic acids with sulfonyl azides is described. 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, compounds4c and4d were found to display potent anti-inflammatory property stronger than that of NSAIDs ibuprofen. Highlights: The iridium(III)-catalyzed ortho -C–H amidation of benzoic acids is described. Anti-inflammatory activity of synthetic anthranilic acids is evaluated. Some synthetic products display anti-inflammatory effect competitive with ibuprofen. 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, compounds4c and4d, 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.