Preparation and biological evaluation of BACE1 inhibitors: Leveraging trans-cyclopropyl moieties as

Winneroski, Leonard L.; Erickson, Jon A.; Green, Steven J.; Lopez, Jose E.; Stout, Stephanie L.; Porter, Warren J.; Timm, David E.; Audia, James E.; Barberis, Mario; Beck, James P.; Boggs, Leonard N.; Borders, Anthony R.; Boyer, Robert D.; Brier, Richard A.; Hembre, Erik J.; Hendle, Jorg; Garcia-Losada, Pablo; Minguez, Jose Miguel; Mathes, Brian M.; May, Patrick C.; Monk, Scott A.; Rankovic, Zoran; Shi, Yuan; Watson, Brian M.; Yang, Zhixiang; Mergott, Dustin J.

doi:10.1016/j.bmc.2019.115194

Preparation and biological evaluation of BACE1 inhibitors: Leveraging trans-cyclopropyl moieties as

Journal Article · Wed Jan 01 04:00:00 EST 2020 · Bioorgan. Med. Chem.

DOI:https://doi.org/10.1016/j.bmc.2019.115194· OSTI ID:1767219

Winneroski, Leonard L.; Erickson, Jon A.; Green, Steven J.; Lopez, Jose E.; Stout, Stephanie L.; Porter, Warren J.; Timm, David E.; Audia, James E.; Barberis, Mario; Beck, James P.; Boggs, Leonard N.; Borders, Anthony R.; Boyer, Robert D.; Brier, Richard A.; Hembre, Erik J.; Hendle, Jorg; Garcia-Losada, Pablo; Minguez, Jose Miguel; Mathes, Brian M.; May, Patrick C. more »

Research Organization:: Advanced Photon Source (APS), Argonne National Laboratory (ANL), Argonne, IL (US)

Sponsoring Organization:: DOE - Office Of Science; INDUSTRY

OSTI ID:: 1767219

Journal Information:: Bioorgan. Med. Chem., Journal Name: Bioorgan. Med. Chem. Journal Issue: (1) Vol. 28

Country of Publication:: United States

Language:: ENGLISH

References (24)

Synthesis of BACE Inhibitor LY2886721. Part I. An Asymmetric Nitrone Cycloaddition Strategy Kolis, Stanley P.; Hansen, Marvin M.; Arslantas, Enver Organic Process Research & Development, Vol. 19, Issue 9 https://doi.org/10.1021/op500351q	journal	August 2015
Tough Times for Medicinal Chemists: Are We to Blame? Tsukamoto, Takashi ACS Medicinal Chemistry Letters, Vol. 4, Issue 4 https://doi.org/10.1021/ml400074k	journal	March 2013
New evolutions in the BACE1 inhibitor field from 2014 to 2018 Hsiao, Chien-Chi; Rombouts, Frederik; Gijsen, Harrie J. M. Bioorganic & Medicinal Chemistry Letters, Vol. 29, Issue 6 https://doi.org/10.1016/j.bmcl.2018.12.049	journal	March 2019
Organic-Catalyst-Mediated Cyclopropanation Reaction Papageorgiou, Charles D.; Ley, Steven V.; Gaunt, Matthew J. Angewandte Chemie International Edition, Vol. 42, Issue 7 https://doi.org/10.1002/anie.200390222	journal	February 2003
The Potent BACE1 Inhibitor LY2886721 Elicits Robust Central A Pharmacodynamic Responses in Mice, Dogs, and Humans May, P. C.; Willis, B. A.; Lowe, S. L. Journal of Neuroscience, Vol. 35, Issue 3 https://doi.org/10.1523/JNEUROSCI.4129-14.2015	journal	January 2015
Biochemistry of Amyloid -Protein and Amyloid Deposits in Alzheimer Disease Masters, C. L.; Selkoe, D. J. Cold Spring Harbor Perspectives in Medicine, Vol. 2, Issue 6 https://doi.org/10.1101/cshperspect.a006262	journal	February 2012
Amyloid precursor protein processing and A 42 deposition in a transgenic mouse model of Alzheimer disease Johnson-Wood, K.; Lee, M.; Motter, R. Proceedings of the National Academy of Sciences, Vol. 94, Issue 4 https://doi.org/10.1073/pnas.94.4.1550	journal	February 1997
What Makes a Great Medicinal Chemist? A Personal Perspective: Miniperspective Murcko, Mark A. Journal of Medicinal Chemistry, Vol. 61, Issue 17 https://doi.org/10.1021/acs.jmedchem.7b01445	journal	April 2018
Functional gamma-secretase inhibitors reduce beta-amyloid peptide levels in brain: γ-secretase inhibitors reduce Aβ levels in PDAPP mouse brain Dovey, H. F.; John, V.; Anderson, J. P. Journal of Neurochemistry, Vol. 76, Issue 1 https://doi.org/10.1046/j.1471-4159.2001.00012.x	journal	January 2001
The “Cyclopropyl Fragment” is a Versatile Player that Frequently Appears in Preclinical/Clinical Drug Molecules Talele, Tanaji T. Journal of Medicinal Chemistry, Vol. 59, Issue 19 https://doi.org/10.1021/acs.jmedchem.6b00472	journal	June 2016
Purification and cloning of amyloid precursor protein β-secretase from human brain Sinha, Sukanto; Anderson, John P.; Barbour, Robin Nature, Vol. 402, Issue 6761 https://doi.org/10.1038/990114	journal	December 1999
β-Amyloid protein increases the vulnerability of cultured cortical neurons to excitotoxic damage Koh, Jae-young; Yang, Linda L.; Cotman, Carl W. Brain Research, Vol. 533, Issue 2 https://doi.org/10.1016/0006-8993(90)91355-K	journal	November 1990
Robust Central Reduction of Amyloid- in Humans with an Orally Available, Non-Peptidic -Secretase Inhibitor May, P. C.; Dean, R. A.; Lowe, S. L. Journal of Neuroscience, Vol. 31, Issue 46 https://doi.org/10.1523/JNEUROSCI.3647-11.2011	journal	November 2011
Stereospecific cyclopentane synthesis via intramolecular nitrone cycloaddition Vinick, Fredric J.; Fengler, Ingrid E.; Gschwend, Heinz W. The Journal of Organic Chemistry, Vol. 42, Issue 17 https://doi.org/10.1021/jo00437a037	journal	August 1977
Soluble protein oligomers in neurodegeneration: lessons from the Alzheimer's amyloid β-peptide Haass, Christian; Selkoe, Dennis J. Nature Reviews Molecular Cell Biology, Vol. 8, Issue 2 https://doi.org/10.1038/nrm2101	journal	February 2007
Alzheimer-type neuropathology in transgenic mice overexpressing V717F β-amyloid precursor protein Games, Dora; Adams, David; Alessandrini, Ree Nature, Vol. 373, Issue 6514 https://doi.org/10.1038/373523a0	journal	February 1995
Enantioselective Organocatalytic Cyclopropanation via Ammonium Ylides Papageorgiou, Charles D.; Cubillo de Dios, Maria A.; Ley, Steven V. Angewandte Chemie International Edition, Vol. 43, Issue 35 https://doi.org/10.1002/anie.200460234	journal	September 2004
Biochemical and kinetic characterization of BACE1: investigation into the putative species-specificity for β- and β′-cleavage sites by human and murine BACE1: Species-specific cleavage in APP by BACE1 Yang, Hsiu-Chiung; Chai, Xiyun; Mosior, Marian Journal of Neurochemistry, Vol. 91, Issue 6 https://doi.org/10.1111/j.1471-4159.2004.02764.x	journal	December 2004
The secretases: enzymes with therapeutic potential in Alzheimer disease De Strooper, Bart; Vassar, Robert; Golde, Todd Nature Reviews Neurology, Vol. 6, Issue 2 https://doi.org/10.1038/nrneurol.2009.218	journal	February 2010
Structure, Sythesis and Absolute Configuration of Leptosphaerin, a Metabolite of the Marine Ascomycete Leptosphaeria oraemaris. White, James D.; Badger, Rodney A.; Kezar, Hollis S. Tetrahedron, Vol. 45, Issue 21 https://doi.org/10.1016/S0040-4020(01)89133-X	journal	January 1989
Preparation and biological evaluation of conformationally constrained BACE1 inhibitors Winneroski, Leonard L.; Schiffler, Matthew A.; Erickson, Jon A. Bioorganic & Medicinal Chemistry, Vol. 23, Issue 13 https://doi.org/10.1016/j.bmc.2015.04.062	journal	July 2015
Alzheimer’s Disease Clinical Trials: Moving Toward Successful Prevention Rafii, Michael S.; Aisen, Paul S. CNS Drugs, Vol. 33, Issue 2 https://doi.org/10.1007/s40263-018-0598-1	journal	December 2018
Conformational Restriction Approach to β-Secretase (BACE1) Inhibitors: Effect of a Cyclopropane Ring To Induce an Alternative Binding Mode Yonezawa, Shuji; Yamamoto, Takahiko; Yamakawa, Hidekuni Journal of Medicinal Chemistry, Vol. 55, Issue 20 https://doi.org/10.1021/jm3011405	journal	September 2012
Integration of in Silico and in Vitro Tools for Scaffold Optimization during Drug Discovery: Predicting P-Glycoprotein Efflux Desai, Prashant V.; Sawada, Geri A.; Watson, Ian A. Molecular Pharmaceutics, Vol. 10, Issue 4 https://doi.org/10.1021/mp300555n	journal	March 2013

Similar Records

Preparation and biological evaluation of conformationally constrained BACE1 inhibitors

Journal Article · Wed Jul 01 00:00:00 EDT 2015 · Bioorgan. Med. Chem. · OSTI ID:1856369

Preparation and biological evaluation of conformationally constrained BACE1 inhibitors

Journal Article · Tue Jun 30 20:00:00 EDT 2015 · Bioorganic and Medicinal Chemistry · OSTI ID:1250967

Discovery of potent iminoheterocycle BACE1 inhibitors

Journal Article · Fri Sep 18 00:00:00 EDT 2015 · Bioorg. Med. Chem. Lett. · OSTI ID:1194208

Preparation and biological evaluation of BACE1 inhibitors: Leveraging trans-cyclopropyl moieties as

Citation Formats

References (24)

Similar Records

Related Subjects