title: Stereoselective Synthesis of Homoneryl and Homogeranyl Triazole Bisphosphonates.
abstract: Isoprenoid-substituted bisphosphonates are known to serve as inhibitors of the enzyme geranylgeranyl diphosphate synthase, and their activity can be highly sensitive to olefin stereochemistry. A mixture of homogeranyl and homoneryl triazole bisphosphonates has previously demonstrated potent activity, and thus stereocontrolled syntheses of the individual isomers have been developed.
authors.affiliation: Department of Chemistry, University of Iowa , Iowa City, Iowa 52242-1294, United States.
authors.forename: Robert A
authors.initials: RA
authors.lastname: Matthiesen
authors.affiliation: Department of Chemistry, University of Iowa , Iowa City, Iowa 52242-1294, United States.
authors.forename: Veronica S
authors.initials: VS
authors.lastname: Wills
authors.affiliation: Department of Chemistry, University of Iowa , Iowa City, Iowa 52242-1294, United States.
authors.forename: Joseph I
authors.initials: JI
authors.lastname: Metzger
authors.affiliation: Division of Oncology and Hematology, Department of Internal Medicine, University of Nebraska Medical Center , Omaha, Nebraska 68198-7680, United States.
authors.forename: Sarah A
authors.initials: SA
authors.lastname: Holstein
authors.affiliation: Department of Chemistry, University of Iowa , Iowa City, Iowa 52242-1294, United States.
authors.forename: David F
authors.initials: DF
authors.lastname: Wiemer
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D004164:Diphosphonates / Q000737:chemistry* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology; D051231:Farnesyltranstransferase / Q000037:antagonists & inhibitors; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
chemical_list: D004164:Diphosphonates; D004791:Enzyme Inhibitors; D014230:Triazoles; D051231:Farnesyltranstransferase