title: Synthesis and binding affinities of fluoroalkylated raloxifenes.
abstract: 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.
authors.affiliation: Department of Chemistry, Inha University, 253 Yonghyundong, Namgu, 402-751, Inchon, South Korea.
authors.forename: Kyo Chul
authors.initials: KC
authors.lastname: Lee
authors.forename: Byung Seok
authors.initials: BS
authors.lastname: Moon
authors.forename: Jae Hak
authors.initials: JH
authors.lastname: Lee
authors.forename: Kyoo-Hyun
authors.initials: KH
authors.lastname: Chung
authors.forename: John A
authors.initials: JA
authors.lastname: Katzenellenbogen
authors.forename: Dae Yoon
authors.initials: DY
authors.lastname: Chi
mesh_terms: D005466:Fluorocarbons / Q000138:chemical synthesis* / Q000378:metabolism; D020849:Raloxifene Hydrochloride / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D011960:Receptors, Estrogen / Q000378:metabolism*; D020845:Selective Estrogen Receptor Modulators / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*
chemical_list: D005466:Fluorocarbons; D011960:Receptors, Estrogen; D020845:Selective Estrogen Receptor Modulators; D020849:Raloxifene Hydrochloride