Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition

Bioorg Med Chem. 2008 Sep 15;16(18):8607-18. doi: 10.1016/j.bmc.2008.08.006. Epub 2008 Aug 7.

Abstract

In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC(50) value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC(50) value of 400 nM. In order to reduce its CYP2D6 inhibitory activity, we performed further systematic structural modifications on 1. In particular, we focused on reducing the number of lipophilic moieties in the biphenyl part of 1, using ClogD(7.4) values as the reference index of lipophilicity. This research led to the identification of N-{(3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3-yl}-3-(piperidin-1-ylcarbonyl)isonicotinamide 1-oxide (30) which showed comparable CCR3 inhibitory activity (IC(50)=23 nM) with much reduced CYP2D6 inhibitory activity (IC(50)=29,000 nM) compared with 1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Calcium / chemistry
  • Calcium / metabolism
  • Cytochrome P-450 CYP2D6 Inhibitors*
  • Cytoplasm / chemistry
  • Cytoplasm / metabolism
  • Drug Design*
  • Humans
  • Hydrocarbons, Fluorinated / chemical synthesis
  • Hydrocarbons, Fluorinated / pharmacology*
  • Inhibitory Concentration 50
  • Naphthalenes / chemical synthesis
  • Naphthalenes / pharmacology*
  • Receptors, CCR3 / antagonists & inhibitors*
  • Receptors, CCR3 / metabolism
  • Structure-Activity Relationship

Substances

  • CCR3 protein, human
  • Cytochrome P-450 CYP2D6 Inhibitors
  • Hydrocarbons, Fluorinated
  • Naphthalenes
  • Receptors, CCR3
  • Calcium