Angular methoxy-substituted furo- and pyranoquinolinones as blockers of the voltage-gated potassium channel Kv1.3

J Med Chem. 2001 Apr 12;44(8):1249-56. doi: 10.1021/jm001007u.

Abstract

The voltage-gated potassium channel Kv1.3 constitutes an attractive target for immunosuppression because of its role in T-lymphocyte activation and its functionally restricted expression to lymphocytes. Blockade of Kv1.3 channels by margatoxin has previously been shown to prevent T-cell activation and attenuate immune responses in vivo. In the present study, several furo- and pyranoquinoline derivatives were synthesized and screened for their blocking activities of Kv1.3 channels, stably expressed in mice-fibroblasts L929. In addition the activities of the compounds on Kv currents of the neuroblastoma cell line N1E-115 were determined. The most potent compounds, the angular furoquinolinone 8-methoxy-2-(1'-methylethyl)-5-methyl-4,5-dihydrofuro[3,2-c]quinolin-4-one (8c) and the angular pyranoquinolinone 9-methoxy-2,2,6-trimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinolin-5-one (9a), inhibited Kv1.3 channels with half-blocking concentrations of 5 and 10 microM, respectively, and displayed 8-fold (8c) and 2-fold (9a) selectivity over Kv currents of N1E-115 cells. Thus, compounds 8c and 9a might function as a template for the development of novel immunosuppressants.

MeSH terms

  • Animals
  • Cell Line
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Furans / pharmacology
  • Immunosuppressive Agents / chemical synthesis*
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / pharmacology
  • Kv1.3 Potassium Channel
  • Mice
  • Potassium Channel Blockers*
  • Potassium Channels*
  • Potassium Channels, Voltage-Gated*
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Quinolines / pharmacology
  • Quinolones / chemical synthesis*
  • Quinolones / chemistry
  • Quinolones / pharmacology
  • Sodium Channel Blockers
  • Structure-Activity Relationship

Substances

  • 8-methoxy-2-(1'-methylethyl)-5-methyl-4,5-dihydrofuro(3,2-c)quinolin-4-one
  • 9-methoxy-2,2,6-trimethyl-2,6-dihydro-5H-pyrrano(3,2-c)quinolin-5-one
  • Furans
  • Immunosuppressive Agents
  • Kcna3 protein, mouse
  • Kv1.3 Potassium Channel
  • Potassium Channel Blockers
  • Potassium Channels
  • Potassium Channels, Voltage-Gated
  • Quinolines
  • Quinolones
  • Sodium Channel Blockers