Design and synthesis of novel hydroxyalkylaminomethylchromones for their IL-5 inhibitory activity

Bioorg Med Chem. 2010 Jul 1;18(13):4625-9. doi: 10.1016/j.bmc.2010.05.028. Epub 2010 May 15.

Abstract

A series of hydroxyalkylaminomethylchromone analogs 3 were prepared and evaluated as inhibitors of interleukin-5. The most active analog 3d inhibited interleukin-5 activity with an IC₅₀ of 17.5 μM. The structural requirements of chromone analogs possessing the inhibitory activity against IL-5 could be summarized as: (i) the cyclohexylmethoxy group at 5th position of the A ring, (ii) the planarity of chromone ring, (iii) hydrophobic unit around the B ring with hydroxyl functional group, (iv) the hydrophobic unit which does not have to be a planar and (v) the length of carbon units between amino and hydroxyl group is limited to two.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology
  • Cell Line
  • Chromones / chemical synthesis
  • Chromones / chemistry*
  • Chromones / pharmacology
  • Drug Design
  • Humans
  • Hydrophobic and Hydrophilic Interactions
  • Interleukin-5 / antagonists & inhibitors*
  • Interleukin-5 / metabolism
  • Structure-Activity Relationship

Substances

  • 3-((1-cyclohexyl-3-hydroxypropan-2-ylamino)methyl)-5-(cyclohexylmethoxy)-4H-chromen-4-one
  • Anti-Inflammatory Agents
  • Chromones
  • Interleukin-5