title: Synthesis and anti-inflammatory evaluation of N-sulfonyl anthranilic acids via Ir(III)-catalyzed C-H amidation of benzoic acids.
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.
authors.affiliation: School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
authors.forename: Sang Hoon
authors.initials: SH
authors.lastname: Han
authors.affiliation: School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
authors.forename: Hyo Sun
authors.initials: HS
authors.lastname: Suh
authors.affiliation: School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
authors.forename: Hyeim
authors.initials: H
authors.lastname: Jo
authors.affiliation: School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
authors.forename: Yongguk
authors.initials: Y
authors.lastname: Oh
authors.affiliation: School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
authors.forename: Neeraj Kumar
authors.initials: NK
authors.lastname: Mishra
authors.affiliation: School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
authors.forename: Sangil
authors.initials: S
authors.lastname: Han
authors.affiliation: School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
authors.forename: Hyung Sik
authors.initials: HS
authors.lastname: Kim
authors.affiliation: School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea; Biocenter, Gyeonggido Business & Science Accelerator (GBSA), Suwon 16229, Republic of Korea.
authors.forename: Young Hoon
authors.initials: YH
authors.lastname: Jung
authors.affiliation: School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea. Electronic address: bmlee@skku.edu.
authors.forename: Byung Mu
authors.initials: BM
authors.lastname: Lee
authors.affiliation: School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea. Electronic address: insukim@skku.edu.
authors.forename: In Su
authors.initials: IS
authors.lastname: Kim
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001565:Benzoates / Q000737:chemistry*; D002384:Catalysis; D051546:Cyclooxygenase 2 / Q000378:metabolism; D053583:Interleukin-1beta / Q000378:metabolism; D007495:Iridium / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000633:toxicity; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D009584:Nitrogen / Q000737:chemistry; D000067996:RAW 264.7 Cells; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D062367:ortho-Aminobenzoates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: C000622263:2-(4-bromophenylsulfonamido)-6-methylbenzoic acid; C000622262:2-(4-methoxyphenylsulfonamido)-6-methylbenzoic acid; D000893:Anti-Inflammatory Agents; D001565:Benzoates; D053583:Interleukin-1beta; D008070:Lipopolysaccharides; D013449:Sulfonamides; D062367:ortho-Aminobenzoates; D007495:Iridium; D051546:Cyclooxygenase 2; D009584:Nitrogen
keywords: Anthranilic acids; Anti-inflammatory; Benzoic acids; Iridium; Sulfonyl azides