Enhanced potency of perfluorinated thalidomide derivatives for inhibition of LPS-induced tumor necrosis factor-α production is associated with a change of mechanism of action

Satomi Niwayama, Christine Loh, Benjamin E. Turk, Jun O. Liu, Hiroyuki Miyachi, Yuichi Hashimoto

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21 Citations (Scopus)


Perfluorination of phthalimides leads to dramatically increased potency as inhibitors of TNF-α production. We examined the enantiodependence for several tetrafluorophthalimides and α-methylthalidomide, 3. Only 3 exhibited strikingly enantiodependent activity. The key structural determinant for the enhanced activity is the tetrafluorophthaloyl group, which confers enhanced potency and a change in the mechanism of inhibition.

Original languageEnglish
Pages (from-to)1071-1076
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Issue number9
Publication statusPublished - May 1998
Externally publishedYes


ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

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