Design, synthesis, and biological evaluation of substituted hydrazone and pyrazole derivatives as selective COX-2 inhibitors: Molecular docking study

Magda A.A. El-Sayed, Naglaa I. Abdel-Aziz, Alaa A.M. Abdel-Aziz, Adel S. El-Azab, Yousif A. Asiri, Kamal E.H. Eltahir

Research output: Contribution to journalJournal articlepeer-review

146 Scopus citations

Abstract

New arylhydrazone derivatives and a series of 1,5-diphenyl pyrazoles were designed and synthesized from 1-(4-chlorophenyl)-4,4,4-trifuorobutane-1,3-dione 1. The newly synthesized compounds were investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw oedema model. Moreover, they were tested for their inhibitory activity against ovine COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay. Some of the new compounds (2f, 6a and 6d) showed a reasonable in vitro COX-2 inhibitory activity, with IC50 value of 0.45 μM and selectivity index of 111.1. A virtual screening was carried out through docking the designed compounds into the COX-2 binding site to predict if these compounds have analogous binding mode to the COX-2 inhibitors. Docking study of the synthesized compounds 2f, 6a and 6d into the active site of COX-2 revealed a similar binding mode to SC-558, a selective COX-2 inhibitor.

Original languageEnglish
Pages (from-to)3416-3424
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume19
Issue number11
DOIs
StatePublished - 1 Jun 2011
Externally publishedYes

Keywords

  • Hydrazone and pyrazole derivatives
  • Molecular docking
  • Selective COX-2 inhibitors

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