title: Pentafluorosulfanyl-containing flufenamic acid analogs: Syntheses, properties and biological activities.
abstract: Pentafluorosulfanyl-containing analogs of flufenamic acid have been synthesized in high yields. Computationally, pKa, LogP and LogD values have been determined. Initial bioactivity studies reveal effects as ion channel modulators and inhibitory activities on aldo-keto reductase 1C3 (AKR1C3) as well as COX-1 and COX-2.
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056 Aachen, Germany.
authors.forename: Christine M M
authors.initials: CM
authors.lastname: Hendriks
authors.affiliation: Center of Excellence in Environmental Toxicology, Department of Systems Pharmacology and Translational Therapeutics, Perelman School of Medicine, University of Pennsylvania, 1315 BRBII/III, 421 Curie Blvd, Philadelphia, PA 19104-6160, United States.
authors.forename: Trevor M
authors.initials: TM
authors.lastname: Penning
authors.affiliation: Center of Excellence in Environmental Toxicology, Department of Systems Pharmacology and Translational Therapeutics, Perelman School of Medicine, University of Pennsylvania, 1315 BRBII/III, 421 Curie Blvd, Philadelphia, PA 19104-6160, United States.
authors.forename: Tianzhu
authors.initials: T
authors.lastname: Zang
authors.affiliation: Institute of Physiology, Universitätsklinikum Aachen, RWTH Aachen University, Pauwelsstraße 30, D-52074 Aachen, Germany.
authors.forename: Dominik
authors.initials: D
authors.lastname: Wiemuth
authors.affiliation: Institute of Physiology, Universitätsklinikum Aachen, RWTH Aachen University, Pauwelsstraße 30, D-52074 Aachen, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Gründer
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056 Aachen, Germany.
authors.forename: Italo A
authors.initials: IA
authors.lastname: Sanhueza
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056 Aachen, Germany.
authors.forename: Franziska
authors.initials: F
authors.lastname: Schoenebeck
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056 Aachen, Germany.
authors.forename: Carsten
authors.initials: C
authors.lastname: Bolm
mesh_terms: D015096:3-Hydroxysteroid Dehydrogenases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D000074425:Aldo-Keto Reductase Family 1 Member C3; D051545:Cyclooxygenase 1 / Q000378:metabolism*; D051546:Cyclooxygenase 2 / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D005439:Flufenamic Acid / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D006911:Hydroxyprostaglandin Dehydrogenases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D004791:Enzyme Inhibitors; D013438:Sulfhydryl Compounds; D005439:Flufenamic Acid; D015096:3-Hydroxysteroid Dehydrogenases; D006911:Hydroxyprostaglandin Dehydrogenases; C487341:AKR1C3 protein, human; D000074425:Aldo-Keto Reductase Family 1 Member C3; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2
keywords: AKR1C3 inhibitor; Bile acid-sensitive ion channel; Computational conformational analyses; Flufenamic acid; Ion channel modulator; Pentafluorosulfanyl group