title: Synthesis and monoamine transporter affinity of 3alpha-arylmethoxy-3beta-arylnortropanes.
abstract: A series of 3-arylnortrop-2-enes and 3alpha-arylmethoxy-3beta-arylnortropanes were synthesized and evaluated for binding affinity at monoamine transporters. The 3-(3,4-dichlorophenyl)nortrop-2-ene (6e) exhibited high affinity for the SERT (K(i)=0.3 nM). The 3alpha-arylmethoxy-3beta-arylnortropanes were generally SERT selective with the 3alpha-(3.4-dichlorophenylmethoxy)-3betaphenylnortrop-2-ene (7c) possessing subnanomolar potency (K(i)=0.061 nM). However, 3alpha-(3,4-dichlorophenylmethoxy)-3beta-phenylnortrop-2-ene (7b) exhibited high affinity at all three transporters [(DAT K(i)=22 nM), (SERT K(i)=6 nM) and (NET K(i)=101 nM)].
authors.affiliation: Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA.
authors.forename: Harneet
authors.initials: H
authors.lastname: Kaur
authors.forename: Sari
authors.initials: S
authors.lastname: Izenwasser
authors.forename: Abha
authors.initials: A
authors.lastname: Verma
authors.forename: Dean
authors.initials: D
authors.lastname: Wade
authors.forename: Amy
authors.initials: A
authors.lastname: Housman
authors.forename: Edwin D
authors.initials: ED
authors.lastname: Stevens
authors.forename: David L
authors.initials: DL
authors.lastname: Mobley
authors.forename: Mark L
authors.initials: ML
authors.lastname: Trudell
mesh_terms: D050483:Dopamine Plasma Membrane Transport Proteins / Q000378:metabolism*; D050484:Norepinephrine Plasma Membrane Transport Proteins / Q000378:metabolism*; D009662:Nortropanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D050486:Serotonin Plasma Membrane Transport Proteins / Q000378:metabolism*
chemical_list: C546972:3-(3,4-dichlorophenyl)nortrop-2-ene; C546973:3-(3,4-dichlorophenylmethoxy)-3-phenylnortrop-2-ene; D050483:Dopamine Plasma Membrane Transport Proteins; D050484:Norepinephrine Plasma Membrane Transport Proteins; D009662:Nortropanes; D050486:Serotonin Plasma Membrane Transport Proteins