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

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

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
Volume8
Issue number9
DOIs
Publication statusPublished - May 1998
Externally publishedYes

Fingerprint

Phthalimides
Thalidomide
Tumor Necrosis Factor-alpha
Derivatives
3'-methylthalidomide

ASJC Scopus subject areas

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

Cite this

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

In: Bioorganic and Medicinal Chemistry Letters, Vol. 8, No. 9, 05.1998, p. 1071-1076.

Research output: Contribution to journalArticle

Niwayama, Satomi ; Loh, Christine ; Turk, Benjamin E. ; Liu, Jun O. ; Miyachi, Hiroyuki ; Hashimoto, Yuichi. / 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. In: Bioorganic and Medicinal Chemistry Letters. 1998 ; Vol. 8, No. 9. pp. 1071-1076.
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