Publications

Scientific Journal Publications

At Paraza, science is at the forefront of everything we do. We are dedicated to developing new technologies that will advance the field of drug discovery. Our work, from client partnerships to academic collaborations and in-house research, is regularly featured in top journals. Explore our latest scientific publications to find out how our scientists contribute to better human health, one discovery at a time.

Discovery of Potent, Selective, and Orally Available IRE1 a Inhibitors Demonstrating Comparable PD Modulation to IRE1 Knockdown in a Multiple Myeloma Model

Marie-Gabrielle Braun, Avi Ashkenazi, Ramsay E. Beveridge, Georgette Castanedo, Heidi Ackerly Wallweber, Maureen H. Beresini, Kevin R. Clark, Tom De Bruyn, Liqiang Fu, Paul Gibbons, Fan Jiang, Susan Kaufman, David Kan, James R. Kiefer, Jean-Philippe Leclerc, Alexandre Lemire, Cuong Ly, Ehud Segal, Jessica Sims, Weiru Wang, Wentao Wei, Liang Zhao, Jacob B. Schwarz, and Joachim Rudolph.  Discovery of Potent, Selective, and Orally Available IRE1α Inhibitors Demonstrating Comparable PD Modulation to IRE1 Knockdown in a Multiple Myeloma Model ACS Med. Chem. Lett., 2024, In Press

https://pubs.acs.org/doi/10.1021/acs.jmedchem.3c02425

Activation/Cyclization of 2H-Azirines and 3-Amino-2-fluoropyridines Towards 2-Aryl-Pyrido[2,3-b]pyrazines

Audrey Belouin, Guillaume Pelletier, Frederic Vuillermet, Joanick Bourret, Tess Fortier. Activation/Cyclization of 2H-Azirines and 3-Amino-2-fluoropyridines Towards 2-Aryl-Pyrido[2,3-b]pyrazinesEur. J. Org. Chem. 2024, In Press

https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202400297

Thermal Nickel-Catalyzed N-Arylation of NH-Sulfoximines with (Hetero)aryl Chlorides Enabled by PhPAd-DalPhos Ligation

Samuel A. Fisher, Connor M. Simon, Peter L. Fox, Michael J. Cotnam, Patrick L. DeRoy, and Mark Stradiotto. Thermal Nickel-Catalyzed N-Arylation of NH-Sulfoximines with (Hetero)aryl Chlorides Enabled by PhPAd-DalPhos Ligation Org. Lett. 2024, ASAP

https://pubs.acs.org/doi/10.1021/acs.orglett.3c04152

Discovery of TRPA1 Antagonist GDC-6599: Derisking Preclinical Toxicity and Aldehyde Oxidase Metabolism with a Potential First-In-Class Therapy for Respiratory Disease

Jack A. Terrett, Justin Q. Ly, Paula Katavolos, Catrin Hasselgren, Steven Laing, Fiona Zhong, Elisia Villemure, Martin Déry, Robin Larouche-Gauthier, Huifen Chen, Daniel G. Shore, Wyne P. Lee, Eric Suto, Kevin Johnson, Marjory Brooks, Alyssa Stablein, Francis Beaumier, Léa Constantineau-Forget, Chantal Grand-Maître, Luce Lépissier, Stéphane Ciblat, Claudio Sturino, Yong Chen, Baihua Hu, Justin Elstrott, Vineela Gandham, Victory Joseph, Helen Booler, Gary Cain, Carolina Chou, Aaron Fullerton, Michelle Lepherd, Shannon Stainton, Elizabeth Torres, Konnie Urban, Lanlan Yu, Yu Zhong, Linda Bao, Kang-Jye Chou, Jessica Lin, Wei Zhang, Hank La, Liling Liu, Teresa Mulder, Jun Chen, Tania Chernov-Rogan, Adam R. Johnson, David H. Hackos, Rebecca Leahey, Shannon D. Shields, Alessia Balestrini, Lorena Riol-Blanco, Brian S. Safina, Matthew Volgraf, Steven Magnuson, and Satoko Kakiuchi-Kiyota. Discovery of TRPA1 Antagonist GDC-6599: Derisking Preclinical Toxicity and Aldehyde Oxidase Metabolism with a Potential First-In-Class Therapy for Respiratory Disease J. Med. Chem. 2024, 67, 3287.

https://pubs.acs.org/doi/10.1021/acs.jmedchem.3c02121

Synthesis of Heterodiarylmethanes via Metallaphotoredox Decarboxylative Arylation

Amanda Yaneza, and Alexandria D. M. Jeanneret. Synthesis of Heterodiarylmethanes via Metallaphotoredox Decarboxylative Arylation Synlett 2024, ASAP

https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0042-1751550

Effect of water and protic solvents on polysaccharide-based column efficiency

Alberto dos Santos Pereira. Effect of water and protic solvents on polysaccharide-based column efficiency J. Sep. Sci. 2023, 2300538

https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/10.1002/jssc.202300538

 

Discovery of Selective Tertiary Amide Inhibitors of Cyclin-Dependent Kinase 2 (CDK2)

https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/10.1002/jssc.202300538Mingshuo Zeng, Jessica M. Grandner, Marian C. Bryan, Vishal Verma, Robin Larouche-Gauthier, Jean-Philippe Leclerc, Liang Zhao, Pouyan Haghshenas, Samuel Aubert-Nicol, Arun Yadav, Melissa Ashley, Jacob Z. Chen, Matthew Durk, Karen E. Samy, Marika Nespi, Elizabeth Levy, Karl Merrick, John G. Moffat, Jeremy Murray, Angela Oh, Christine Orr, Ehud Segal, Jessica Sims, Christopher Sneeringer, Madeleine Prangley, Steffan Vartanian, Steven Magnuson, and Brendan T. Parr. Discovery of Selective Tertiary Amide Inhibitors of Cyclin-Dependent Kinase 2 (CDK2) ACS Med. Chem. Lett. 2023, 14, 1179

https://doi.org/10.1021/acsmedchemlett.3c00142

Nickel-Catalyzed N-Arylation of Sulfinamides: A Comparative Study versus Analogous Sulfonamide Cross-Couplings

Connor M. Simon, Katherine N. Robertson, Patrick L. DeRoy, Arun A. Yadav, Erin R. Johnson, Mark Stradiotto Nickel-Catalyzed N-Arylation of Sulfinamides: A Comparative Study versus Analogous Sulfonamide Cross-Couplings Organometallics 2023, 42, 1704

https://doi.org/10.1021/acs.organomet.2c00545

Palladium catalyzed amidation of phenyl carboxylates and anilines using aqueous micellar catalysis

Wanying Zhang, Juliana Smillovich, Vincent Albert. Palladium Catalyzed Amidation of Phenyl Carboxylates and Anilines Using Aqueous Micellar Catalysis Tet. Lett. 2023, 114, 154242

https://doi.org/10.1016/j.tetlet.2022.154242

Mapping Dual-Base-Enabled Nickel-Catalyzed Aryl Amidations: Application in the Synthesis of 4-Quinolones

Ryan T. McGuire, Travis Lundrigan, Joshua W. M. MacMillan, Katherine N. Robertson, Arun A. Yadav, Mark Stradiotto. Mapping Dual-Base-Enabled Nickel-Catalyzed Aryl Amidations: Application in the Synthesis of 4-Quinolones  Angew. Chem. Int. Ed. 2023, 61, e202200352

https://doi.org/10.1002/anie.202200352

Identification of RP-6685, an Orally Bioavailable Compound that Inhibits the DNA Polymerase Activity of Polθ 

Monica Bubenik, Pavel Mader, Philippe Mochirian, Fréderic Vallée, Jillian Clark, Jean-François Truchon, Alexander L. Perryman, Victor Pau, Igor Kurinov, Karl E. Zahn, Marie-Eve Leclaire, Robert Papp, Marie-Claude Mathieu, Martine Hamel, Nicole M. Duffy, Claude Godbout, Matias Casas-Selves, Jean-Pierre Falgueyret, Prasamit S. Baruah, Olivier Nicolas, Rino Stocco, Hugo Poirier, Giovanni Martino, Alexanne Bonneau Fortin, Anne Roulston, Amandine Chefson, Stéphane Dorich, Miguel St-Onge, Purvish Patel, Charles Pellerin, Stéphane Ciblat, Thomas Pinter, Francis Barabé, Majida El Bakkouri, Paranjay Parikh, Christian Gervais, Agnel Sfeir, Yael Mamane, Stephen J. Morris, W. Cameron Black, Frank Sicheri, Michel Gallant. Identification of RP-6685, an Orally Bioavailable Compound that Inhibits the DNA Polymerase Activity of Polθ  J. Med. Chem. 2022, 65, 13198

https://doi.org/10.1021/acs.jmedchem.2c00998

Synthesis and Characterization of an Orally Bioavailable Small Molecule Agonist of the Apelin Receptor 

Sanju Narayanan, Doughua Dai, Ravi Kumar Vyas Devambatla, Vincent Albert, Nicolas Bruneau-Latour, Vineetha Vasukuttan, Stephane Ciblat, Kenneth Rehder, Scott P. Runyon, Rangan Maitra. Synthesis and Characterization of an Orally Bioavailable Small Molecule Agonist of the Apelin Receptor Bioorg. Med. Chem. 2022, 66, 116789

https://doi.org/10.1016/j.bmc.2022.116789

Discovery of SY-5609: A Selective, Noncovalent Inhibitor of CDK7

Jason J. Marineau, Kristin B. Hamman, Shanhu Hu, Sydney Alnemy, Janessa Mihalich, Anzhelika Kabro, Kenneth Matthew Whitmore, Dana K. Winter, Stephanie Roy, Stephane Ciblat, Nan Ke, Anneli Savinainen, Ashraf Wilsily, Goran Malojcic, Robert Zahler, Darby Schmidt, Michael J. Bradley, Nigel J. Waters, Claudio Chuaqui. Discovery of SY-5609: A Selective, Noncovalent Inhibitor of CDK7 J. Med. Chem. 2022, 65, 1458

https://doi.org/10.1021/acs.jmedchem.1c01171

Synthesis of Imidazo[1,2‑a]pyridines: Triflic Anhydride-Mediated Annulation of 2H‑Azirines with 2‑Chloropyridines

Frédéric Vuillermet, Joanick Bourret, Guillaume Pelletier. Synthesis of Imidazo[1,2a]pyridines: Triflic Anhydride-Mediated Annulation of 2HAzirines with 2Chloropyridines J. Org. Chem. 2021, 86, 388

https://doi.org/10.1021/acs.joc.0c02148

A Retrospective Look at the Impact of Binding Site Environment on the Optimization of TRPA1 Antagonists

Elisia Villemure, Jack A. Terrett, Robin Larouche-Gauthier, Martin Déry, Huifen Chen, Rebecca M. Reese, Shannon D. Shields, Jun Chen, Steven Magnuson, Matthew Volgraf. A Retrospective Look at the Impact of Binding Site Environment on the Optimization of TRPA1 Antagonists ACS Med. Chem. Lett. 2021, 12, 1230

https://doi.org/10.1021/acsmedchemlett.1c00305

Tetrahydrofuran-Based Transient Receptor Potential Ankyrin 1 (TRPA1) Antagonists: Ligand Based Discovery, Activity in a Rodent Asthma Model, and Mechanism-of-Action via Cryogenic Electron Microscopy

Jack A. Terrett, Huifen Chen, Daniel G. Shore, Elisia Villemure, Robin Larouche-Gauthier, Martin Déry, Francis Beaumier, Léa Constantineau-Forget, Chantal Grand-Maître, Luce Lépissier, Stéphane Ciblat, Claudio Sturino, Yong Chen, Baihua Hu, Aijun Lu, Yunli Wang, Andrew P. Cridland, Stuart I. Ward, David H. Hackos, Rebecca M. Reese, Shannon D. Shields, Jun Chen, Alessia Balestrini, Lorena Riol-Blanco, Wyne P. Lee, John Liu, Eric Suto, Xiumin Wu, Juan Zhang, Justin Q. Ly, Hank La, Kevin Johnson, Matt Baumgardner, Kang-Jye Chou, Alexis Rohou, Lionel Rougé, Brian S. Safina, Steven Magnuson, Matthew Volgraf. Tetrahydrofuran-Based Transient Receptor Potential Ankyrin 1 (TRPA1) Antagonists: Ligand Based Discovery, Activity in a Rodent Asthma Model, and Mechanism-of-Action via Cryogenic Electron Microscopy J. Med. Chem. 2021, 64, 3843

https://doi.org/10.1021/acs.jmedchem.0c02023

Cp*Rh(III)-Catalyzed C8 C−H Alkylation of Quinoline N-Oxides with Diazo Meldrum's Acid

Malcolm P. Huestis, Jean-Philippe Leclerc, Robin Larouche-Gauthier, Samuel Aubert-Nicol, Arun Yadav, Koilpitchai Sivamuthuraman. Cp*Rh(III)-Catalyzed C8 C−H Alkylation of Quinoline N-Oxides with Diazo Meldrum’s Acid Eur. J. Org. Chem. 2021, 396

https://doi.org/10.1002/ejoc.202001584

 

Identification of BRaf-Sparing Amino-Thienopyrimidines with Potent IREa Inhibitory Activity

Ramsay E. Beveridge, Heidi Ackerly Wallweber, Avi Ashkenazi, Maureen Beresini, Kevin R. Clark, Paul Gibbons, Élise Ghiro, Susan Kaufman, Alexandre Larivée, Mélissa Leblanc, Jean-Philippe Leclerc, Alexandre Lemire, Cuong Ly, Joachim Rudolph, Jacob B. Schwarz, Sanjay Srivastava, Weiru Wang, Liang Zhao, Marie-Gabrielle Braun. Identification of BRaf-Sparing Amino-Thienopyrimidines with Potent IREa Inhibitory Activity ACS Med. Chem. Lett. 202011, 2389

https://doi.org/10.1021/acsmedchemlett.0c00344

 

 

Selective Inhibition of CDK7 Reveals High-Confidence Targets and New Models for TFIIH Function in Transcription

Jenna K. Rimel, Zachary C. Poss, Benjamin Erickso, Zachary L. Maas, Christopher C. Ebmeier, Jared L. Johnson, Tim-Michael Decker, Tomer M. Yaron, Michael J. Bradley, Kristin B. Hamman, Shanhu Hu, Goran Malojcic, Jason J. Marineau, Peter W. White, Martine Brault, Limei Tao, Patrick DeRoy, Christian Clavette, Shraddha Nayak, Leah J. Damon, Ines H. Kaltheuner, Heeyoun Bunch, Lewis C. Cantley, Matthias Geyer, Janet Iwasa, Robin D. Dowell, David L. Bentley, William M. Old, Dylan J. Taatjes. Selective Inhibition of CDK7 Reveals High-Confidence Targets and New Models for TFIIH Function in Transcription Genes & Dev. 202034, 1452

http://www.genesdev.org/cgi/doi/10.1101/gad.341545.120

 

 

Synthesis of α,α-Disubstituted Benzocyclobutane Amino Acids Through [2+2] Annulation of Benzyne with Dehydroalanine

Audrey Picard , Stéphane Ciblat , Yeeman K. Ramtohul. Synthesis of α,α-Disubstituted Benzocyclobutane Amino Acids Through [2+2] Annulation of Benzyne with Dehydroalanine Synlett 2020, 31, 507

https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0039-1691572

The Development of Tropomyosin Receptor Kinase (Trk) Inhibitors as Targeted Cancer Therapeutics

Abhijit Bhat, Stephane Ciblat, Hong Wang, Kollol Pal. The Development of Tropomyosin Receptor Kinase (Trk) Inhibitors as Targeted Cancer Therapeutics Med. Chem. Rev. 2020, 55, 303

https://www.acsmedchem.org/produits.php?langue=english&cle_menus=1187970214&cle_data=24&cle_data_item=40

 

Design of a Brain-Penetrant CDK4/6 Inhibitor for Glioblastoma

Sarah M. Bronner, Karl A. Merrick, Jeremy Murray, Laurent Salphati, John G. Moffat, Jodie Pang, Christopher J. Sneeringer, Nicholas Dompe, Patrick Cyr, Hans Purkey, Gladys de Leon Boenig, Jun Li, Aleksandr Kolesnikov, Robin Larouche-Gauthier, Kwong Wah Lai, Xiaoli Shen, Samuel Aubert-Nicol, Yi-Chen Chen, Jonathan Cheong, James J. Crawford, Marc Hafner, Pouyan Haghshenas, Araz Jakalian, Jean-Philippe Leclerc, Ngiap-Kie Lim, Tom O’Brien, Emile G. Plise, Hadil Shalan, Claudio Sturino, John Wai, Yang Xiao, Jianping Yin, Liang Zhao, Stephen Gould, Alan Olivero, Timothy P. Heffron. Design of a Brain-Penetrant CDK4/6 Inhibitor for Glioblastoma Bioorg. Med. Chem. Lett. 201929, 2294

https://doi.org/10.1016/j.bmcl.2019.06.021

Discovery and Characterization of SY-1365, a Selective, Covalent Inhibitor of CDK7

Shanhu Hu, Jason J. Marineau, Nisha Rajagopal, Kristin B. Hamman, Yoon Jong Choi, Darby R. Schmidt, Nan Ke, Liv Johannessen, Michael J. Bradley, David A. Orlando, Sydney R. Alnemy, Yixuan Ren, Stéphane Ciblat, Dana K. Winter, Anzhelika Kabro, Kevin T. Sprott, J. Graeme Hodgson, Christian C. Fritz, John P. Carulli, Emmanuelle di Tomaso, Eric R. Olson. Discovery and Characterization of SY-1365, a Selective, Covalent Inhibitor of CDK7 Cancer Res. 201979, 3479

https://doi.org/10.1158/0008-5472.CAN-19-0119

1-Thiazol-2-yl-N-3-methyl-1H-pyrozole-5-carboxylic acid derivatives as antitumor agents

Alan B. Cooper, Stéphane Ciblat, Gerald Shipps, Jedd Levine, Matthew Kostura, Vibha Oza, Léa Constantineau-Forget, Martin Déry, Chantal Grand-Maître, Nicolas Bruneau-Latour, Édith Bellavance, Michael Patane, Arshad Siddiqui, Michael Luther. 1-Thiazol-2-yl-N-3-methyl-1H-pyrozole-5-carboxylic acid derivatives as antitumor agents Bioorg. Med. Chem. Lett. 201727, 4471

https://doi.org/10.1016/j.bmcl.2017.08.003

Preparation of 3-O-aryl chloramphenicol derivatives via chemoselective copper-catalyzed O-arylation of (1R,2R)-(−)-N-BOC-2-amino-1-(4-nitrophenyl)-1,3-propanediol using triarylbismuthines

Tabinda Ahmad, Julien Dansereau, Martin Hébert, Chantal Grand-Maître, Alexandre Larivée, Arshad Siddiqui, Alexandre Gagnon. Preparation of 3-O-aryl chloramphenicol derivatives via chemoselective copper-catalyzed O-arylation of (1R,2R)-(−)-N-BOC-2-amino-1-(4-nitrophenyl)-1,3-propanediol using triarylbismuthines Tet. Lett. 201657, 4284

https://doi.org/10.1016/j.tetlet.2016.08.021

Electrolytic Macrocyclizations: Scalable Synthesis of a Diazonamide-Based Drug Development Candidate

Hui Ding, Patrick L. DeRoy, Christian Perreault, Alexandre Larivée, Arshad Siddiqui, Charles G. Caldwell, Susan Harran, Patrick G. Harran. Electrolytic Macrocyclizations: Scalable Synthesis of a Diazonamide-Based Drug Development Candidate Angew. Chem. Int. Ed. 201554, 4818

https://doi.org/10.1002/anie.201411663

 

 

Give us a call or send us an email

If you want to learn more about the Paraza difference, contact us to discuss your specific needs.