Quinolinesulfonamides of aryloxy-/arylthio-ethyl piperidines: influence of an arylether fragment on 5-HT1A/5-HT7 receptor selectivity

Arch Pharm (Weinheim). 2013 Mar;346(3):180-8. doi: 10.1002/ardp.201200322. Epub 2013 Feb 4.

Abstract

The solid-phase synthesis of a new series of 19 biomimetics of long-chain arylpiperazines, namely flexible quinoline sulfonamides of aryl(heteroaryl)oxy-/heteroarylthio-ethyl 4-aminomethylpiperidines, is reported. Various structural modifications applied followed by biological evaluation for 5-HT1A, 5-HT6, and 5-HT7 receptors gave further support of a possible replacement of arylpiperazine with aryloxy-/arylthio-ethyl derivatives of alicyclic amines and control of receptor selectivity upon diversification in the aryl(heteroaryl)oxy-/heteroarylthio-ethyl fragment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drug Design
  • Ethers
  • HEK293 Cells
  • Humans
  • Molecular Structure
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Piperidines / pharmacology
  • Protein Binding
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Quinolines / pharmacology
  • Radioligand Assay
  • Receptor, Serotonin, 5-HT1A / genetics
  • Receptor, Serotonin, 5-HT1A / metabolism*
  • Receptors, Serotonin / genetics
  • Receptors, Serotonin / metabolism*
  • Solid-Phase Synthesis Techniques
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology
  • Transfection

Substances

  • Ethers
  • Piperidines
  • Quinolines
  • Receptors, Serotonin
  • Sulfonamides
  • serotonin 7 receptor
  • Receptor, Serotonin, 5-HT1A