Novel benzofurane-pyrazole derivatives with anti-inflammatory, cyclooxygenase inhibitory and cytotoxicity evaluation

Sahin Z., Ozhan Y., SİPAHİ H., Biltekin S. N., YURTTAŞ L., BERK B., ...More

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES, vol.77, no.7-8, pp.279-285, 2022 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 77 Issue: 7-8
  • Publication Date: 2022
  • Doi Number: 10.1515/znc-2021-0217
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), BIOSIS, CAB Abstracts, Chemical Abstracts Core, EMBASE, MEDLINE, Veterinary Science Database
  • Page Numbers: pp.279-285
  • Keywords: anti-inflammatory, cox-1, cox-2, cylooxygenase, pyrazolone, DESIGN
  • Anadolu University Affiliated: Yes


Novel benzofurane-pyrazolone hybrids have been synthesized for evaluating their anti-inflammatory and cytotoxic properties. 4-(2-chloroacetyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one were reacted with alpha-hydroxy aldehyde or alpha-hydroxy ketone derivatives to obtain nine novel pyrazolone derivatives. Structures were successfully elucidated by H-1 NMR, C-13 NMR, IR and HRMS. Enzyme inhibitory activity was measured on cyclooxygenases (COXs) as considered to address anti-inflammatory activity. Compound 2 showed the highest activity on both COX-1 and COX-2 subtypes with 12.0 mu M and 8.0 mu M IC50, respectively. This activity was found close to indomethacin COX-2 inhibition measured as 7.4 mu M IC50. Rest of the compounds (1, 3-9) showed 10.4-28.1 mu M IC50 on COX-2 and 17.0-35.6 mu M IC50 on COX-1 (Compound 1 has no activity on COX-1). Tested compounds (1-9) showed activity on NO production. Only compound was the 4, which showed a low inhibition on IL-6 levels. Cell viability was up to 60% at 100 mu M for all compounds (1-9) on RAW 264.7 and NIH3T3 cell lines, thus compounds were reported to be noncytotoxic.