title: Fluorinated pyrrolidines and piperidines incorporating tertiary benzenesulfonamide moieties are selective carbonic anhydrase II inhibitors.
abstract: A series of substituted pyrrolidines and piperidines were synthesized using superacid HF/SbF5 chemistry. Investigated as inhibitors of several human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, i.e. the cytosolic hCA I and II as well as the tumor-associated transmembrane isoforms hCA IX and XII, these compounds showed a never yet reported selectivity toward the human carbonic anhydrase hCA II. In the tertiary benzenesulfonamide family, this class of inhibitors points out a new mechanism of action for human carbonic anhydrase II inhibition.
authors.affiliation: a @rtMolecule , Poitiers , France .
authors.forename: Alexandre
authors.initials: A
authors.lastname: Le Darz
authors.forename: Agnès
authors.initials: A
authors.lastname: Mingot
authors.forename: Fodil
authors.initials: F
authors.lastname: Bouazza
authors.forename: Ugo
authors.initials: U
authors.lastname: Castelli
authors.forename: Omar
authors.initials: O
authors.lastname: Karam
authors.forename: Muhammet
authors.initials: M
authors.lastname: Tanc
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
authors.forename: Sébastien
authors.initials: S
authors.lastname: Thibaudeau
mesh_terms: D024402:Carbonic Anhydrase II / Q000037:antagonists & inhibitors* / Q000378:metabolism; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006801:Humans; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry / Q000494:pharmacology*; D011759:Pyrrolidines / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000737:chemistry / Q000494:pharmacology*; D000096926:Benzenesulfonamides
chemical_list: D024402:Carbonic Anhydrase II; D002257:Carbonic Anhydrase Inhibitors; D010880:Piperidines; D011759:Pyrrolidines; D013449:Sulfonamides; D000096926:Benzenesulfonamides
keywords: Carbonic anhydrase; fluorine; selectivity; superacid; tertiary benzenesulfonamides