Identification of novel chromenone derivatives as interleukin-5 inhibitors

Eeda Venkateswararao, Min Seok Kim, Vinay K. Sharma, Ki Cheul Lee, Santhosh Subramanian, Eunmiri Roh, Youngsoo Kim, Sang Hun Jung

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

A series of (E)-5-alkoxy-3-(3-phenyl-3-oxoprop-1-enyl)-4H-chromen-4-ones (4) and (E)-5-alkoxy-3-(3-hydroxy-3-phenylprop-1-enyl)-4H-chromen-4-ones (5) were synthesized and evaluated for their IL-5 inhibitory activity. Propenone analogs 4 possess some of the structurally important characteristics of isoflavone 2 and chalcone 3 previously known as potent IL-5 inhibitor. However, the inhibitory activity of 4 was weak and therefore this structural hybridization appears to be ineffective for the design of IL-5 inhibitor. Meanwhile the potent activity profile of compounds 5 was discovered. This enhanced activity of 5 compared to 4 could be due to the effective location of hydroxyl group of allylic alcohol moiety of 5 in the 3D structure. The electron withdrawing substituents at position 4 of phenyl ring of 5 enhances the activity possibly due to an increase in the strength of hydrogen bonding property of hydroxyl group of allylic alcohol moiety.

Original languageEnglish (US)
Pages (from-to)31-38
Number of pages8
JournalEuropean Journal of Medicinal Chemistry
Volume59
DOIs
StatePublished - Jan 1 2013

Keywords

  • Chromenone analogs
  • Eosinophils
  • Inhibitor
  • Interleukin-5

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