Design, synthesis, anti-inflammatory activity and molecular docking of potential novel antipyrine and pyrazolone analogs as cyclooxygenase enzyme (COX) inhibitors

Mardia T. El Sayed*, Marwa A.M.Sh El-Sharief, Eman S. Zarie, Nesrin M. Morsy, Ahmed R. Elsheakh, Andrey Voronkov, Vladimir Berishvili, Ghada S. Hassan

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

13 Citations (Scopus)

Abstract

As a part of a directed program for development of new active agents, novel heterocyclic derivatives with antipyrine and pyrazolone moieties -incorporated in- have been designed and synthesized. Starting with 4-arylidene-3-methyl-1-phenyl-5-pyrazolone derivative 2a,b novel Mannich bases derivatives have been synthesized and biologically evaluated for their anti-inflammatory activity. Furthermore, the activity of such compounds has been tested interestingly as COX-1 and COX-2 inhibitors. Structure elucidation of the synthesized compounds was attained by the use of elemental analysis, IR, 1H NMR, 13C NMR, and Mass spectrometry techniques. Compounds 3b, 3d and 4b represent the high % inhibition values for both COX-1 and COX-2. On the other hand, compound 8 showed little selectivity against COX-2 while compound 10 showed good selectivity against COX-1 only. Structure activity relationship has been discussed and the results were confirmed by molecular docking calculations.

Original languageEnglish
Pages (from-to)952-957
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume28
Issue number5
DOIs
Publication statusPublished - 1 Mar 2018
MoE publication typeA1 Journal article-refereed

Keywords

  • Anti-inflammatory activity
  • Antipyrine
  • COX-1
  • COX-2
  • Molecular modeling
  • Pyrazolone derivatives
  • Synthesis

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