Synthesis, in silico studies and cytotoxicity evaluation of novel 1,3,4-oxadiazole derivatives designed as potential mPGES-1 inhibitors

Gizem Erensoy, Kai Ding, Chang Guo Zhan, Ammar Elmezayen, Kemal Yelekçi, Merve Duracik, Özlem Bingöl Özakpinar, İlkay Küçükgüzel

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

A series of new 1,3,4-oxadizole derivatives containing thioether group, has been synthesized to investigate their mPGES-1 inhibitory activities. The synthesized compounds were also evaluated for their anticancer and COX-1/2 inhibitory activities. All compounds were checked for their purity using TLC and HPLC analyses. The melting points, elemental analysis, FT-IR, 1H-/13C-NMR and LR-MS data were utilized for structural characterization. The most potent derivative was 2-[5-{[2-methyl-5-(propan-2-yl)phenoxy]methyl}-1,3,4-oxadiazol-2-yl)sulphanyl]-1(phenyl)ethan-1-one 3a, which showed inhibitory activity against mPGES-1 with an IC50 of 4.95 μM. Docking studies with mPGES-1 and COX-1/2 enzymes revealed their affinity and potential binding mechanism for the tested compounds.

Original languageEnglish
Pages (from-to)436-451
Number of pages16
JournalJournal of Research in Pharmacy
Volume24
Issue number4
DOIs
StatePublished - 2020

Bibliographical note

Funding Information:
Acknowledgements: This study was supported by Marmara University Scientific Research Projects Commission under the grant no: SAG-C-DRP-081117-0616.

Publisher Copyright:
© 2020 Marmara University Press.

Keywords

  • 1,3,4-Oxadiazoles
  • ADME prediction
  • Anticancer activity
  • COX-1/2 inhibition
  • MPGES-1 inhibition
  • Molecular docking
  • Thioethers

ASJC Scopus subject areas

  • Pharmacology, Toxicology and Pharmaceutics (all)
  • Pharmacology (medical)

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