Efficient syntheses of 2-(3',5'-difluorophenyl)-3-(4'- methylsulfonylphenyl)-cyclopent-2-enone, a potent COX-2 inhibitor

Dalian Zhao, Xu Feng, Cheng yi Chen, Rich D. Tillyer, Edward J.J. Grabowski, Paul J. Reider, Cameron Black, Nathalie Quimet, Peppi Prasit

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

2-(3',5'-Difluorophenyl)-3-(4'-methylsulfonylphenyl)cyclopent-2-enone (1) displays high selectivity and potency against COX-2. Three efficient syntheses of this diarylcyclopentenone are described. The first approach employs a Suzuki coupling reaction as the key step while the second synthesis features an intramolecular Friedel-Crafts acylation. The third, and preferred route to this compound involves a sequential malonate alkylation and acylation and ring-closure sequence.

Original languageEnglish (US)
Pages (from-to)6001-6018
Number of pages18
JournalTetrahedron
Volume55
Issue number19
DOIs
StatePublished - May 7 1999
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • Acylation
  • Alkylation
  • COX-II inhibitor
  • Suzuki coupling
  • Synthesis

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