Comprehensive Strategies to Bicyclic Prolines: Applications in the Synthesis of Potent Arginase Inhi

Li, Derun; Zhang, Hongjun; Lyons, Thomas W.; Lu, Min; Achab, Abdelghani; Pu, Qinglin; Childers, Matthew; Mitcheltree, Matthew J.; Wang, Jialiang; Martinot, Theodore A.; McMinn, Spencer E.; Sloman, David L.; Palani, Anandan; Beard, Adam; Nogle, Lisa; Gathiaka, Symon; Sauri, Josep; Kim, Hai-Young; Adpressa, Donovon; Spacciapoli, Peter; Miller, J. Richard; Palte, Rachel L.; Lesburg, Charles A.; Cumming, Jared; Fischer, Christian

doi:10.1021/acsmedchemlett.1c00258

Comprehensive Strategies to Bicyclic Prolines: Applications in the Synthesis of Potent Arginase Inhi

Journal Article · 01 October 2021 · ACS Med. Chem. Lett.

DOI:https://doi.org/10.1021/acsmedchemlett.1c00258· OSTI ID:1844614

Li, Derun; Zhang, Hongjun; Lyons, Thomas W.; Lu, Min; Achab, Abdelghani; Pu, Qinglin; Childers, Matthew; Mitcheltree, Matthew J.; Wang, Jialiang; Martinot, Theodore A.; McMinn, Spencer E.; Sloman, David L.; Palani, Anandan; Beard, Adam; Nogle, Lisa; Gathiaka, Symon; Sauri, Josep; Kim, Hai-Young; Adpressa, Donovon; Spacciapoli, Peter more »

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: DOE - Office Of Science; INDUSTRY

OSTI ID:: 1844614

Journal Information:: ACS Med. Chem. Lett., Vol. 12, Issue (11)

Country of Publication:: United States

Language:: ENGLISH

References (49)

Collagen Structure and Stability Shoulders, Matthew D.; Raines, Ronald T. Annual Review of Biochemistry, Vol. 78, Issue 1 https://doi.org/10.1146/annurev.biochem.77.032207.120833	journal	June 2009
The crystal structure of DL -proline hydrochloride Mitsui, Y.; Tsuboi, M.; Iitaka, Y. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry, Vol. 25, Issue 11 https://doi.org/10.1107/S0567740869005449	journal	November 1969
Collagen Stability: Insights from NMR Spectroscopic and Hybrid Density Functional Computational Investigations of the Effect of Electronegative Substituents on Prolyl Ring Conformations DeRider, Michele L.; Wilkens, Steven J.; Waddell, Michael J. Journal of the American Chemical Society, Vol. 124, Issue 11 https://doi.org/10.1021/ja0166904	journal	February 2002
Arginase Inhibitors: A Rational Approach Over One Century: AN EXHAUSTIVE REVIEW OF ARGINASE INHIBITORS Pudlo, Marc; Demougeot, Céline; Girard-Thernier, Corine Medicinal Research Reviews, Vol. 37, Issue 3 https://doi.org/10.1002/med.21419	journal	November 2016
L-arginine metabolism in myeloid cells controls T-lymphocyte functions Bronte, Vincenzo; Serafini, Paolo; Mazzoni, Alessandra Trends in Immunology, Vol. 24, Issue 6 https://doi.org/10.1016/S1471-4906(03)00132-7	journal	June 2003
Regulation of arginase I activity and expression by both PD-1 and CTLA-4 on the myeloid-derived suppressor cells Liu, Yu; Yu, Yinyan; Yang, Suguang Cancer Immunology, Immunotherapy, Vol. 58, Issue 5 https://doi.org/10.1007/s00262-008-0591-5	journal	October 2008
Inhibition of arginase by CB-1158 blocks myeloid cell-mediated immune suppression in the tumor microenvironment Steggerda, Susanne M.; Bennett, Mark K.; Chen, Jason Journal for ImmunoTherapy of Cancer, Vol. 5, Issue 1 https://doi.org/10.1186/s40425-017-0308-4	journal	December 2017
Binding of α,α-Disubstituted Amino Acids to Arginase Suggests New Avenues for Inhibitor Design Ilies, Monica; Di Costanzo, Luigi; Dowling, Daniel P. Journal of Medicinal Chemistry, Vol. 54, Issue 15 https://doi.org/10.1021/jm200443b	journal	August 2011
Discovery of ( R )-2-Amino-6-borono-2-(2-(piperidin-1-yl)ethyl)hexanoic Acid and Congeners As Highly Potent Inhibitors of Human Arginases I and II for Treatment of Myocardial Reperfusion Injury Van Zandt, Michael C.; Whitehouse, Darren L.; Golebiowski, Adam Journal of Medicinal Chemistry, Vol. 56, Issue 6 https://doi.org/10.1021/jm400014c	journal	March 2013
Discovery of N -Substituted 3-Amino-4-(3-boronopropyl)pyrrolidine-3-carboxylic Acids as Highly Potent Third-Generation Inhibitors of Human Arginase I and II Van Zandt, Michael C.; Jagdmann, G. Erik; Whitehouse, Darren L. Journal of Medicinal Chemistry, Vol. 62, Issue 17 https://doi.org/10.1021/acs.jmedchem.9b00931	journal	August 2019
Discovery and Optimization of Rationally Designed Bicyclic Inhibitors of Human Arginase to Enhance Cancer Immunotherapy Mitcheltree, Matthew J.; Li, Derun; Achab, Abdelghani ACS Medicinal Chemistry Letters, Vol. 11, Issue 4 https://doi.org/10.1021/acsmedchemlett.0c00058	journal	March 2020
Structure-Based Discovery of Proline-Derived Arginase Inhibitors with Improved Oral Bioavailability for Immuno-Oncology Lu, Min; Zhang, Hongjun; Li, Derun ACS Medicinal Chemistry Letters, Vol. 12, Issue 9 https://doi.org/10.1021/acsmedchemlett.1c00195	journal	July 2021
Development of a Zinc-Mediated Approach to a 2,3- cis -Pyrrolidine Arginase Inhibitor Lyons, Thomas W.; Martinot, Theodore A.; He, Cyndi Qixin Organic Process Research & Development, Vol. 24, Issue 8 https://doi.org/10.1021/acs.oprd.0c00171	journal	June 2020
A Spectrophotometric Assay of Arginase Han, Shoufa; Viola, Ronald E. Analytical Biochemistry, Vol. 295, Issue 1 https://doi.org/10.1006/abio.2001.5189	journal	August 2001
Escaping from Flatland: Antimalarial Activity of sp ³ -Rich Bridged Pyrrolidine Derivatives Cox, Brian; Duffy, James; Zdorichenko, Victor ACS Medicinal Chemistry Letters, Vol. 11, Issue 12 https://doi.org/10.1021/acsmedchemlett.0c00486	journal	November 2020
Bicyclic proline analogues as organocatalysts for stereoselective aldol reactions: an in silico DFT study Shinisha, C. B.; Sunoj, Raghavan B. Organic & Biomolecular Chemistry, Vol. 5, Issue 8 https://doi.org/10.1039/b701688c	journal	January 2007
Chiral, bicyclic proline derivatives and their application as ligands for copper in the catalytic asymmetric allylic oxidation of olefins Södergren, Mikael J.; Andersson, Pher G. Tetrahedron Letters, Vol. 37, Issue 42 https://doi.org/10.1016/0040-4039(96)01664-4	journal	October 1996
Synthesis of [ c ]-Fused Bicyclic Proline Analogues: Synthesis of [ c ]-Fused Bicyclic Proline Analogues Calaza, M. Isabel; Sayago, Francisco J.; Laborda, Pedro European Journal of Organic Chemistry, Vol. 2015, Issue 8 https://doi.org/10.1002/ejoc.201403121	journal	January 2015
Asymmetric Synthesis of Unsaturated, Fused Bicyclic Proline Analogues through Amino Alkylation of Cyclic Bis(allylsulfoximine)titanium Complexes and Migratory Cyclization of δ-Amino Alkenyl Aminosulfoxonium Salts Koep, Stefan; Gais, Hans-Joachim; Raabe, Gerhard Journal of the American Chemical Society, Vol. 125, Issue 43 https://doi.org/10.1021/ja030324y	journal	October 2003
Synthesis of Bicyclic Proline Derivatives by the Aza-Cope-Mannich Reaction: Formal Synthesis of (±)-Acetylaranotin Belov, Dmitry S.; Ratmanova, Nina K.; Andreev, Ivan A. Chemistry - A European Journal, Vol. 21, Issue 10 https://doi.org/10.1002/chem.201405811	journal	January 2015
Iridium-catalyzed hydroboration of alkenes with pinacolborane Yamamoto, Yasunori; Fujikawa, Rhyou; Umemoto, Tomokazu Tetrahedron, Vol. 60, Issue 47 https://doi.org/10.1016/j.tet.2004.09.014	journal	November 2004
A new method of synthesis of methyl N-Boc-2,3-dehydropyrrolidine- and piperidine-2-carboxylates Kublitskii, V. S.; Stepanov, A. E.; Trukhan, V. M. Russian Journal of Organic Chemistry, Vol. 44, Issue 6 https://doi.org/10.1134/S1070428008060274	journal	June 2008
Correlations between catalytic reactions of diazo compounds and stoichiometric reactions of transition-metal carbenes with alkenes. Mechanism of the cyclopropanation reaction Doyle, Michael P.; Griffin, John H.; Bagheri, Vahid Organometallics, Vol. 3, Issue 1 https://doi.org/10.1021/om00079a011	journal	January 1984
Asymmetric construction of benzylic quaternary carbons from chiral malonates: Formal synthesis of natural (−)aphanorphine Fadel, Antoine; Arzel, Philippe Tetrahedron: Asymmetry, Vol. 6, Issue 4 https://doi.org/10.1016/0957-4166(95)00097-9	journal	April 1995
A Convenient Two-Step Procedure for the Synthesis of Substituted Allylic Amines from Allylic Alcohols Sen, Stephanie E.; Roach, Steven L. Synthesis, Vol. 1995, Issue 07 https://doi.org/10.1055/s-1995-4012	journal	July 1995
A Novel Class of Tunable Zinc Reagents (RXZnCH ₂ Y) for Efficient Cyclopropanation of Olefins Lorenz, Jon C.; Long, Jiang; Yang, Zhiqiang The Journal of Organic Chemistry, Vol. 69, Issue 2 https://doi.org/10.1021/jo030312v	journal	December 2003
Finding the Perfect Match: A Combined Computational and Experimental Study toward Efficient and Scalable Photosensitized [2 + 2] Cycloadditions in Flow Williams, Jason D.; Nakano, Momoe; Gérardy, Romaric Organic Process Research & Development, Vol. 23, Issue 1 https://doi.org/10.1021/acs.oprd.8b00375	journal	December 2018
Synthesis of Cyclobutane-Fused Angular Tetracyclic Spiroindolines via Visible-Light-Promoted Intramolecular Dearomatization of Indole Derivatives Zhu, Min; Zheng, Chao; Zhang, Xiao Journal of the American Chemical Society, Vol. 141, Issue 6 https://doi.org/10.1021/jacs.8b12965	journal	January 2019
Asymmetric synthesis of S-(−)-cucurbitine Williams, Robert M.; Fegley, Glenn J. Tetrahedron Letters, Vol. 33, Issue 45 https://doi.org/10.1016/S0040-4039(00)61768-9	journal	November 1992
Synthesis of Spirocyclic Pyrrolidines: Advanced Building Blocks for Drug Discovery Chalyk, Bohdan A.; Butko, Maryna V.; Yanshyna, Oksana O. Chemistry - A European Journal, Vol. 23, Issue 66 https://doi.org/10.1002/chem.201702362	journal	October 2017
A novel approach to 2,4-ethanoproline Grygorenko, Oleksandr O.; Komarov, Igor V.; Cativiela, Carlos Tetrahedron: Asymmetry, Vol. 20, Issue 12 https://doi.org/10.1016/j.tetasy.2009.05.003	journal	July 2009
trans-3-n-propyl-L-proline is a highly favorable, conformationally restricted replacement for methionine in the C-terminal tetrapeptide of cholecystokinin. Stereoselective synthesis of 3-allyl- and 3-n-propyl-L-proline derivatives from 4-hydroxy-L-proline Holladay, Mark W.; Lin, Chun Wel; May, Catherine S. Journal of Medicinal Chemistry, Vol. 34, Issue 1 https://doi.org/10.1021/jm00105a068	journal	January 1991
Efficient method for inversion of secondary alcohols by reaction of chloromethanesulfonates with cesium acetate Shimizu, Takeshi; Hiranuma, Sayoko; Nakata, Tadashi Tetrahedron Letters, Vol. 37, Issue 34 https://doi.org/10.1016/0040-4039(96)01333-0	journal	August 1996
Responsive Mn(II) complexes for potential applications in diagnostic Magnetic Resonance Imaging Rolla, Gabriele A.; Tei, Lorenzo; Fekete, Marianna Bioorganic & Medicinal Chemistry, Vol. 19, Issue 3 https://doi.org/10.1016/j.bmc.2010.07.064	journal	February 2011
Synthesis and properties of pinanediol .alpha.-amido boronic esters Matteson, Donald S.; Jesthi, Pradipta K.; Sadhu, Kizhakethil M. Organometallics, Vol. 3, Issue 8 https://doi.org/10.1021/om00086a024	journal	August 1984
Synthesis and Anti-HIV Activity of d - and l -Thietanose Nucleosides Choo, Hyunah; Chen, Xin; Yadav, Vikas Journal of Medicinal Chemistry, Vol. 49, Issue 5 https://doi.org/10.1021/jm050912h	journal	February 2006
Use of hexamethylphosphoramide chmpa in the alkylation of aromatic amines: synthesis of azetidines, pyrrolidines, piperidines and hexahydroazepines Juaristi, Eusebio; Madrigal, Domingo Tetrahedron, Vol. 45, Issue 3 https://doi.org/10.1016/0040-4020(89)80091-2	journal	January 1989
Synthetic Strategy toward the Pentacyclic Core of Melodinus Alkaloids Goli, Navya; Kallepu, Shivakrishna; Mainkar, Prathama S. The Journal of Organic Chemistry, Vol. 83, Issue 4 https://doi.org/10.1021/acs.joc.7b03138	journal	January 2018
Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates Yoneyama, Hiroki; Numata, Masahiro; Uemura, Kenji The Journal of Organic Chemistry, Vol. 82, Issue 11 https://doi.org/10.1021/acs.joc.7b00346	journal	May 2017
Synthesis of Chiral Tetrahydrofuran Building Blocks from Pantolactones: Application in the Synthesis of Empagliflozin and Amprenavir Analogs: Synthesis of Chiral Tetrahydrofuran Building Blocks from Pantolactones: Application in the Synthesis of Empagliflozin and Amprenavir Analogs Athawale, Paresh R.; Kumari, Neeta; Dandawate, Monica R. European Journal of Organic Chemistry, Vol. 2019, Issue 30 https://doi.org/10.1002/ejoc.201900718	journal	July 2019
Total syntheses of the squalene-derived halogenated polyethers ent -dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades Underwood, Brian S.; Tanuwidjaja, Jessica; Ng, Sze-Sze Tetrahedron, Vol. 69, Issue 25 https://doi.org/10.1016/j.tet.2013.04.041	journal	June 2013
A scalable synthesis of (1R,3S,5R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid Wang, Gan; James, Clint A.; Meanwell, Nicholas A. Tetrahedron Letters, Vol. 54, Issue 49 https://doi.org/10.1016/j.tetlet.2013.09.114	journal	December 2013
[2+2] Cycloaddition reaction of cyclic enecarbamates and enamides with ketenes. A short and efficient synthesis of the Geissman-Waiss lactone. de Faria, Antônio R.; Matos, Carlos Roberto R.; Correia, Carlos Roque D. Tetrahedron Letters, Vol. 34, Issue 1 https://doi.org/10.1016/S0040-4039(00)60049-7	journal	January 1993
A new method for the deoxygenation of secondary alcohols Barton, Derek H. R.; McCombie, Stuart W. Journal of the Chemical Society, Perkin Transactions 1, Issue 16 https://doi.org/10.1039/p19750001574	journal	January 1975
Small Molecule Conformational Preferences Derived from Crystal Structure Data. A Medicinal Chemistry Focused Analysis Brameld, Ken A.; Kuhn, Bernd; Reuter, Deborah C. Journal of Chemical Information and Modeling, Vol. 48, Issue 1 https://doi.org/10.1021/ci7002494	journal	December 2007
A Medicinal Chemist’s Guide to Molecular Interactions Bissantz, Caterina; Kuhn, Bernd; Stahl, Martin Journal of Medicinal Chemistry, Vol. 53, Issue 14 https://doi.org/10.1021/jm100112j	journal	July 2010
Enantiospecific Synthesis of Heterocycles from α-Amino Acids Sardina, F. Javier; Rapoport, Henry Chemical Reviews, Vol. 96, Issue 6 https://doi.org/10.1021/cr9300348	journal	January 1996
Organic synthesis provides opportunities to transform drug discovery Blakemore, David C.; Castro, Luis; Churcher, Ian Nature Chemistry, Vol. 10, Issue 4 https://doi.org/10.1038/s41557-018-0021-z	journal	March 2018
The importance of synthetic chemistry in the pharmaceutical industry Campos, Kevin R.; Coleman, Paul J.; Alvarez, Juan C. Science, Vol. 363, Issue 6424 https://doi.org/10.1126/science.aat0805	journal	January 2019

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