title: A new synthesis of difluoromethanesulfonamides--a novel pharmacophore for carbonic anhydrase inhibition.
abstract: Preparation of the key intermediate carboxydifluoromethanesulfonamide provides direct synthetic access to a wide range of novel difluoromethanesulfonamides, including the acetazolamide analogue (2-ethanoylamino-1,3,4-thiadiazol-5-yl)-difluoromethanesulfonamide. Their water solubility and stability, ether partition coefficient, pK(a) and submicromolar dissociation constants for human carbonic anhydrase isozyme II (HCA II) make them promising candidates for topical glaucoma therapy.
authors.affiliation: Krebs Institute, Chemistry Department, Sheffield University, Sheffield, UK S3 7HF.
authors.forename: Nicholas A
authors.initials: NA
authors.lastname: Boyle
authors.forename: W Richard
authors.initials: WR
authors.lastname: Chegwidden
authors.forename: G Michael
authors.initials: GM
authors.lastname: Blackburn
mesh_terms: D024402:Carbonic Anhydrase II / Q000037:antagonists & inhibitors / Q000737:chemistry*; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007527:Isoenzymes / Q000037:antagonists & inhibitors; D015394:Molecular Structure; D012995:Solubility; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D002257:Carbonic Anhydrase Inhibitors; D006845:Hydrocarbons, Fluorinated; D007527:Isoenzymes; D013449:Sulfonamides; D024402:Carbonic Anhydrase II