title: Synthesis of Kappa Opioid Antagonists Based On Pyrrolo[1,2-α]quinoxalinones Using an N-Arylation/Condensation/Oxidation Reaction Sequence.
abstract: The quinoxaline and quinoxalinone family of nitrogen heterocycles is present in molecules of therapeutic relevance for diverse applications ranging from infectious diseases to neuroscience targets. Here, we describe a general synthetic sequence to afford pyrrolo[1,2-α]quinoxalinones from commercially available starting materials and their use in preparing potential kappa opioid receptor antagonists. The biological data obtained from the latter set of compounds is briefly presented and discussed.
authors.affiliation: Division of Chemical Biology and Medicinal Chemistry, University of North Carolina , 125 Mason Farm Road, CB 7363, Chapel Hill, North Carolina 27599, United States.
authors.forename: Sarah M
authors.initials: SM
authors.lastname: Scarry
authors.affiliation: Departments of Molecular Therapeutics and Neuroscience, The Scripps Research Institute , 130 Scripps Way, #2A2, Jupiter, Florida 33458, United States.
authors.forename: Kimberly M
authors.initials: KM
authors.lastname: Lovell
authors.affiliation: Division of Chemical Biology and Medicinal Chemistry, University of North Carolina , 125 Mason Farm Road, CB 7363, Chapel Hill, North Carolina 27599, United States.
authors.forename: Kevin J
authors.initials: KJ
authors.lastname: Frankowski
authors.affiliation: Departments of Molecular Therapeutics and Neuroscience, The Scripps Research Institute , 130 Scripps Way, #2A2, Jupiter, Florida 33458, United States.
authors.forename: Laura M
authors.initials: LM
authors.lastname: Bohn
authors.affiliation: Division of Chemical Biology and Medicinal Chemistry, University of North Carolina , 125 Mason Farm Road, CB 7363, Chapel Hill, North Carolina 27599, United States.
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Aubé
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D066244:Proton Magnetic Resonance Spectroscopy; D011758:Pyrroles / Q000737:chemistry*; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000737:chemistry; D017473:Receptors, Opioid, kappa / Q000037:antagonists & inhibitors*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D011758:Pyrroles; D011810:Quinoxalines; D017473:Receptors, Opioid, kappa