Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands.
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Gu X, Izenwasser S, Wade D, Housman A, Gulasey G, Rhoden JB, Savoie CD, Mobley DL, Lomenzo SA, Trudell ML
Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands.
Bioorg Med Chem. 2010 Dec 1;18(23):8356-64. doi: 10.1016/j.bmc.2010.09.060. Epub 2010 Sep 29.
- PubMed ID
- 20980153 [ View in PubMed]
- 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).
DrugBank Data that Cites this Article
- Drug Targets
Drug Target Kind Organism Pharmacological Action Actions Meperidine Sodium-dependent dopamine transporter Protein Humans UnknownInhibitorDetails Meperidine Sodium-dependent noradrenaline transporter Protein Humans UnknownInhibitorDetails Meperidine Sodium-dependent serotonin transporter Protein Humans UnknownBinderDetails