Stereoselective Synthesis of Homoneryl and Homogeranyl Triazole Bisphosphonates

Robert A Matthiesen; Veronica S Wills; Joseph I Metzger; Sarah A Holstein; David F Wiemer

doi:10.1021/acs.joc.6b01693

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Stereoselective Synthesis of Homoneryl and Homogeranyl Triazole Bisphosphonates

Journal article

Peer reviewed

Stereoselective Synthesis of Homoneryl and Homogeranyl Triazole Bisphosphonates

Robert A Matthiesen, Veronica S Wills, Joseph I Metzger, Sarah A Holstein and David F Wiemer

Journal of organic chemistry, Vol.81(19), pp.9438-9442

10/07/2016

DOI: 10.1021/acs.joc.6b01693

PMCID: PMC5297151

PMID: 27648672

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https://www.ncbi.nlm.nih.gov/pmc/articles/5297151View

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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.

Spectrometry, Mass, Electrospray Ionization

Proton Magnetic Resonance Spectroscopy

Stereoisomerism

Triazoles - chemistry

Diphosphonates - chemistry

Enzyme Inhibitors - chemistry

Carbon-13 Magnetic Resonance Spectroscopy

Enzyme Inhibitors - pharmacology

Farnesyltranstransferase - antagonists & inhibitors

Diphosphonates - pharmacology

Details

Title: Subtitle: Stereoselective Synthesis of Homoneryl and Homogeranyl Triazole Bisphosphonates
Creators: Robert A Matthiesen - Department of Chemistry, University of Iowa , Iowa City, Iowa 52242-1294, United States
Veronica S Wills - Department of Chemistry, University of Iowa , Iowa City, Iowa 52242-1294, United States
Joseph I Metzger - Department of Chemistry, University of Iowa , Iowa City, Iowa 52242-1294, United States
Sarah A Holstein - Division of Oncology and Hematology, Department of Internal Medicine, University of Nebraska Medical Center , Omaha, Nebraska 68198-7680, United States
David F Wiemer - Department of Chemistry, University of Iowa , Iowa City, Iowa 52242-1294, United States
Resource Type: Journal article
Publication Details: Journal of organic chemistry, Vol.81(19), pp.9438-9442
DOI: 10.1021/acs.joc.6b01693
PMID: 27648672
PMCID: PMC5297151
NLM abbreviation: J Org Chem
ISSN: 0022-3263
eISSN: 1520-6904
Publisher: United States
Grant note: T32 GM008365 / NIGMS NIH HHS R01 CA172070 / NCI NIH HHS
Language: English
Date published: 10/07/2016
Academic Unit: Neuroscience and Pharmacology; Chemistry
Record Identifier: 9983985803702771

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