title: The solid-phase Zincke reaction: preparation of omega-hydroxy pyridinium salts in the search for CFTR activation.
abstract: A study of structural modifications of MPB-07 was undertaken as part of a synthetic program aimed at discovering small molecules with CFTR activation potential. Solid-phase synthesis techniques were used to prepare derivatives of MPB-07 employing the Zincke reaction for the construction of aromatic, quaternary ammonium salts such as those found in 2 or 3. In this transformation, primary amines react with highly electrophilic N-2,4-dinitrophenylpyridinium (DNP) salt 4 to afford pyridinium salt 8 with release of 2,4-dinitroaniline 6. Thus, the reaction of 1-(2,4-dinitrophenyl)pyridinium salts with various polymer-bound amino ethers, followed by cleavage from the resin, delivers the desired salts in good yield and high purity.
authors.affiliation: Department of Chemistry, University of California, Davis 95616-5295, USA.
authors.forename: M
authors.initials: M
authors.lastname: Eda
authors.forename: M J
authors.initials: MJ
authors.lastname: Kurth
authors.forename: M H
authors.initials: MH
authors.lastname: Nantz
mesh_terms: D019005:Cystic Fibrosis Transmembrane Conductance Regulator / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011726:Pyridinium Compounds / Q000737:chemistry*
chemical_list: D011726:Pyridinium Compounds; D019005:Cystic Fibrosis Transmembrane Conductance Regulator