Synthesis and binding affinities of fluoroalkylated raloxifenes

Kyo Chul Lee, Byung Seok Moon, Jae Hak Lee, Kyoo Hyun Chung, John A. Katzenellenbogen, Dae Yoon Chi

Research output: Contribution to journalArticlepeer-review


Three fluoroalkylated derivatives (1-3) of the selective estrogen receptor modulator (SERM), raloxifene, have been synthesized. The key step in the synthesis is the C-C bond formation of benzo[b]thiophene and a substituted phenyl group (ring C) using a Stille reaction. The in vitro binding affinities of the substituted raloxifenes 1-3 are 45, 60, 89%, respectively, relative to the affinity of estradiol, which is higher than the affinity of raloxifene itself (25%). When labeled with the positron-emitting radionuclide, these compounds might be useful as PET imaging agents for estrogen receptor-positive breast tumors.

Original languageEnglish (US)
Pages (from-to)3649-3658
Number of pages10
JournalBioorganic and Medicinal Chemistry
Issue number17
StatePublished - Aug 15 2003

ASJC Scopus subject areas

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


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