title: Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands.
abstract: A series of benzyl esters of meperidine and normeperidine were synthesized and evaluated for binding affinity at serotonin, dopamine and norepinephrine transporters. The 4-methoxybenzyl ester 8b and 4-nitrobenzyl ester 8c in the meperidine series and 4-methoxybenzyl ester 14a in the normeperidine series exhibited low nanomolar binding affinities at the SERT (K(i) values <2nM) and high SERT selectivity (DAT/SERT >1500 and NET/SERT >1500).
authors.affiliation: Department of Chemistry, University of New Orleans, LA 70148, USA.
authors.forename: Xiaobo
authors.initials: X
authors.lastname: Gu
authors.forename: Sari
authors.initials: S
authors.lastname: Izenwasser
authors.forename: Dean
authors.initials: D
authors.lastname: Wade
authors.forename: Amy
authors.initials: A
authors.lastname: Housman
authors.forename: Gerard
authors.initials: G
authors.lastname: Gulasey
authors.forename: Jill B
authors.initials: JB
authors.lastname: Rhoden
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Savoie
authors.forename: David L
authors.initials: DL
authors.lastname: Mobley
authors.forename: Stacey A
authors.initials: SA
authors.lastname: Lomenzo
authors.forename: Mark L
authors.initials: ML
authors.lastname: Trudell
mesh_terms: D004952:Esters; D008024:Ligands; D008614:Meperidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D050486:Serotonin Plasma Membrane Transport Proteins / Q000737:chemistry* / Q000378:metabolism; D017367:Selective Serotonin Reuptake Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D004952:Esters; D008024:Ligands; D008614:Meperidine; D050486:Serotonin Plasma Membrane Transport Proteins; D017367:Selective Serotonin Reuptake Inhibitors; C002752:normeperidine