Publications

Front COVER

2023

Development of LM-41 and AF-2112, two flufenamic acid-derived TEAD inhibitors obtained through the replacement of the trifluoromethyl group by aryl rings

Ahmed Fnaiche, Léa Mélin, Narjara González Suárez, Alexis Paquin, Victoria Vu, Fengling Li, Abdellah Allali-Hassani, Albina Bolotokova, Frédéric Allemand, Muriel Gelin, Philippe Cotelle, Simon Woo, Steven R. LaPlante, Dalia Barsyte-Lovejoy, Vijayaratnam Santhakumar, Masoud Vedadi, Jean-François Guichou, Borhane Annabi, Alexandre Gagnon

2023, Bioorganic & Medicinal Chemistry Letters, In Press, doi.org/10.1016/j.bmcl.2023.129488

BMCL TEAD Gagnon Graphical Abstract.tiff

Synthesis of 1-Methylcyclopropyl Aryl Ethers from Phenols using an Alkenylation-Cyclopropanation Sequence

Bianca Bueno, Suzanne Heurtaux and Alexandre Gagnon

2023, Journal of Organic Chemistry, 13351-13357 DOI: doi.org/10.1021/acs.joc.3c01289

On the Barton Copper-Catalyzed C3-Arylation of Indoles using Triarylbismuth bis(trifluoroacetate) Reagents

Ahmed Fnaiche, Bianca Bueno, Claire L. McMullin, Alexandre Gagnon

ChemPlusChem, 2023 e202200465 DOI: 10.1002/cplu.202200465

2023

2022

On the Copper-Promoted Backbone Arylation of Histidine-Containing Peptides using Triarylbismuthines

Hwai-Chien Chan, Alexandre Gagnon

Synthesis, 2022, 54, 16, 3568-3587 DOI: 10.1055/a-1786-6578

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2021

Copper-Promoted N-Arylation of the Imidazole Side Chain of Protected Histidine by Using Triarylbismuth Reagents

Hwai-Chien Chan, Bianca Bueno, Adrien Le Roch, Alexandre Gagnon

ChemEurJ, 2021, 27, 53, 13330-13336 DOI: 10.1002/chem.202102186

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Development of LM98, a Small-Molecule TEAD Inhibitor Derived from Flufenamic Acid

Léa Mélin, Shuay Abdullayev, Ahmed Fnaiche, Victoria Vu, Narjara Gonzalez Suarez, Hong Zeng, Magdalena Szewczyk, Fengling Li, Guillermo Sinisterra, Abdellah Allali-Hassani, Irene Chau, Aiping Dong, Simon Woo, Borhane Annabi, Levon Halabelian, Steven LaPlante, Masoud Vedadi, Dalia Barsyte-Lovejoy, Vijayaratnam Santhakumar, Alexandre Gagnon

ChemMedChem, 2021, 16, 19, 2982-3002 DOI: 10.1002/cmdc.202100432

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Design and Synthesis of LM146, a Potent Inhibitor of PB1 with an Improved Selectivity Profile over SMARCA2

Léa Mélin, Emily Gesner, Sarah Attwell, Olesya A. Kharenko, Edward H. Van Der Horst, Henrik C. Hansen, Alexandre Gagnon

ACS Omega, 2021, 6, 33, 21327-21338 DOI: 10.1021/acsomega.1c01555

Synthesis of NVS-BPTF-1 and evaluation of its biological activity

Léa Mélin, Cyrus Calosing,Olesya A. Kharenko, Henrik C. Hansen, Alexandre Gagnon

BMCL, 2021, 47, 128208 DOI: 10.1016/j.bmcl.2021.128208

2020

Copper-Promoted O‐Arylation of the Phenol Side Chain of Tyrosine using Triarylbismuthines

Adrien Le Roch, Martin Hébert, Alexandre Gagnon

EurJOC, 2020, 33, 5363 DOI: 10.1002/ejoc.202000790

Copper-Promoted N‐Arylation of the Indole Side Chain of Tryptophan using Triarylbismuthines

Adrien Le Roch, Hwai-Chien Chan, Alexandre Gagnon

EurJOC, 2020, 36, 5815 DOI: 10.1002/ejoc.202000667

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Heavy metal orchestration

Adrien Le Roch, Alexandre Gagnon

Nature Chemistry, 2020, 12, 223-224 DOI: 10.1038/s41557-020-0434-3

2019

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acids

Emeline Benoit, Ahmed Fnaiche, Alexandre Gagnon

Beilstein J. Org. Chem., 2019, 15, 1162 DOI: 10.3762/bjoc.15.113

First use of an organobismuth reagent in C(sp3)–S bond formation: Access to aryl cyclopropyl sulfides via copper-catalyzed S-cyclopropylation of thiophenols using tricyclopropylbismuth

Emeline Benoit, Bianca Bueno, Catherine Choinière, Alexandre Gagnon

J. Organomet. Chem., 2019, 893, 72 DOI: 10.1016/j.jorganchem.2019.04.032

Synthesis of NSC 106084 and NSC 14778 and evaluation of their DNMT inhibitory activity

Maxime Leroy, Léa Mélin, Steven R. LaPlante, José L. Medina-Franco, Alexandre Gagnon

Bioorg. Med. Chem. Lett., 2019, 29, 826 DOI: 10.1016/j.bmcl.2019.01.022

2018

Copper-Catalyzed Beta-Iodovinylation of Carbamates: Expedient Access to Highly Functionalized Vinyl-Carbamates

Simon Ricard, Alexandre Gagnon, Benoit Daoust

ChemistrySelect, 2018, 4923 DOI: 10.1002/slct.201800824

Bismuth Compounds

Alexandre Gagnon, Emeline Benoit, Adrien Le Roch

Science of synthesis knowledge updates 2018/4

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2017

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction between Aryl(Heteroaryl)iodides and Tricyclopropylbismuth: Expedient Access to Aryl Cyclopropylketones

Emeline Benoit, Julien Dansereau, Alexandre Gagnon

Synlett, 2017, 2833 DOI: 10.1055/s-0036-1590832

Synthesis of Highly Functionalized Diaryl Ketones by Palladium-Catalyzed Carbonylative Cross-Coupling Reaction Between Triarylbismuthines and Aryl(Heteroaryl) Iodides

Julien Dansereau, Stéphane Gautreau, Alexandre Gagnon

Chemistry Select, 2017, 2593 DOI: 10.1002/slct.201700438

Organobismuth Reagents: Synthesis, Properties and Applications in Organic Synthesis

Alexandre Gagnon, Julien Dansereau, Adrien Le Roch

Synthesis, 2017, 49, 1707 DOI: 10.1055/s-0036-1589482

2016

Preparation of 3-O-aryl chloramphenicol derivatives via 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

Tetrahedron Lett., 2016, 57, 4284 DOI: 10.1016/j.tetlet.2016.08.021

Synthesis of Highly Functionalized Triarylbismuthines by Functional Group Manipulation and Use in Palladium- and Copper-Catalyzed Arylation Reactions

Martin Hébert, Pauline Petiot, Emeline Benoit, Julien Dansereau, Tabinda Ahmad, Adrien Le Roch, Xavier Ottenwaelder, Alexandre Gagnon

J. Org. Chem., 2016, 81, 5401 DOI: 10.1021/acs.joc.6b00767

Chapter 3: Drug Discovery Methods

Marie Lopez, Maxime Leroy, Chantal Etievant, Frédéric Ausseil, Alexandre Gagnon, Paola Arimondo

Drug Discovery in Cancer Epigenetics, 2016, 63 DOI: 10.1016/B978-0-12-802208-5.00003-5

2015

Mechanism-Driven Elaboration of an Enantioselective Bromocyclopropanation Reaction of Allylic Alcohols

Sylvain Taillemaud, Nicolas Diercxsens, Alexandre Gagnon, André B. Charette

Angew. Chem. Int. Ed., 2015, 54, 14108 DOI: 10.1002/anie.201506083

Discovery, design and synthesis of indole-based EZH2 inhibitors

Victor S. Gehling, Rishi G. Vaswani, Christopher G. Nasveschuk, Martin Duplessis, Priyadarshini Iyer, Srividya Balasubramanian, Feng Zhao, Andrew C. Good, Robert Campbell, Christina Lee, Les A. Dakin, Andrew S. Cook, Alexandre Gagnon, Jean-Christophe Harmange, James E. Audia, Richard T. Cummings, Emmanuel Normant, Patrick Trojer, Brian K. Albrecht

Bioorg. Med. Chem. Lett., 2015, 25, 3644 DOI: 10.1016/j.bmcl.2015.06.056

Aza Follow-ups to BI 207524, a Thumb Pocket 1 HCV NS5B Polymerase Inhibitor. Part 1: Mitigating the Genotoxic Liability of an Aniline Metabolite

Pierre Beaulieu, Gordon Bolger, Martin Duplessis, Alexandre Gagnon, Michel Garneau, Timothy Stammers, George Kukolj, Jianmin Duan

Bioorg. Med. Chem. Lett., 2015, 25, 1135 DOI: 10.1016/j.bmcl.2014.12.028

Multi-Parameter Optimization of Aza-follow-ups to BI 207524, a thumb pocket 1 HCV NS5B Polymerase Inhibitor. Part 2: Impact of Lipophilicity on Promiscuity and in vivo Toxicity

Pierre Beaulieu, Gordon Bolger, Dan Deon, Martin Duplessis, Gulrez Fazal, Alexandre Gagnon, Michel Garneau, Steven LaPlante, Timothy Stammers, George Kukolj, Jianmin Duan

Bioorg. Med. Chem. Lett., 2015, 25, 1140 DOI: 10.1016/j.bmcl.2014.12.078

Spontaneous grafting of 9,10-phenanthrenequinone on porous carbon as active electrode material in electrochemical capacitor in alkaline electrolyte

Annaïg Le Comte, Danny Chhin, Alexandre Gagnon, Richard Retoux and Daniel Bélanger

J. Mater. Chem. A., 2015, 4, 1562 DOI: 10.1039/C4TA05536E

Copper-Catalyzed O-arylation of N-protected 1,2-aminoalcohols using functionalized trivalent organobismuth reagents

Pauline Petiot, Julien Dansereau, Martin Hébert, Imene Khene, Tabinda Ahmad, Samira Samaali, Maxime Leroy, Francis Pinsonneault, Claude Y. Legault and Alexandre Gagnon

Org. Biomol. Chem., 2015, 13, 1322 DOI: 10.1039/C4OB02497D

2014

Copper-Catalyzed N-Arylation of Azoles and Diazoles using Highly Functionalized Trivalent Organobismuth Reagents

Pauline Petiot, Julien Dansereau and Alexandre Gagnon

RSC Advances, 2014, 22255 DOI: 10.1039/C4RA02467B

Discovery and Optimization of Tetramethylpiperidinyl Benzamides as Inhibitors of EZH2

Christopher G. Nasveschuk*, Alexandre Gagnon, Shivani Garapaty-Rao, Srividya Balasubramanian, Robert Campbell, Christina Lee, Feng Zhao, Louise Bergeron, Richard Cummings, Patrick Trojer, James E. Audia, Brian K. Albrecht and Jean-Christophe P. Harmange

ACS Med. Chem. Lett., 2014, 378 DOI: 10.1021/ml400494b

Synthesis of Highly Functionalized Diaryl Ethers by Copper-Mediated O-Arylation of Phenols using Trivalent Arylbismuth Reagents

Cynthia Crifar, Pauline Petiot, Tabinda Ahmad and Alexandre Gagnon

Chem. Eur. J., 2014, 20, 2755 DOI: 10.1002/chem.201303684

Palladium-Catalyzed Cross-Coupling Reaction of Trialkylbismuthines with 2-Haloazines and Diazines

Pauline Petiot and Alexandre Gagnon

Heterocycles, 2014, 1615 DOI: 10.3987/COM-13-S(S)114

2013

Anthranilic acid-based Thumb Pocket 2 HCV NS5B polymerase inhibitors with sub-micromolar potency in the cell-based replicon assay

Timothy A. Stammers,* René Coulombe, Martin Duplessis, Gulrez Fazal, Alexandre Gagnon, Michel Garneau, Sylvie Goulet, Araz Jakalian, Steven LaPlante, Jean Rancourt, Bounkham Thavonekham, Dominik Wernic, George Kulolg and Pierre Beaulieu

Bioorg. Med. Chem. Lett., 2013, 23, 6879 DOI: 10.1016/j.bmcl.2013.09.102

Identification of EZH2 and EZH1 Small Molecule Inhibitors with Selective Impact on Diffuse Large B Cell Lymphoma Cell Growth

Shivani Garapaty-Rao, Christopher Nasveschuk, Alexandre Gagnon, Eric Y. Chan, Peter Sandy, Jennifer Busby, Srividya Balasubramanian, Robert Campbell, Feng Zhao, Louise Bergeron, James E. Audia, Brian K. Albrecht, Jean-Christophe Harmange, Richard Cummings and Patrick Trojer

Chem. & Biol., 2013, 20, 1329 DOI: 10.1016/j.chembiol.2013.09.013

Preparation of phenylethylbenzamide derivatives as modulators of DNMT3 activity

Anzhelika Kabro, Hugo Lachance, Iris Marcoux-Archambault, Valérie Perrier, Vicky Doré, Christina Gros, Véronique Masson, Jean-Marc Gregoire, Frédéric Ausseil, David Cheishvili, Nathalie Bibens Laulan, Yves St-Pierre, Moshe Szyf, Paola B. Arimondo and Alexandre Gagnon

Med. Chem. Commun., 2013, 1562 DOI: 10.1039/C3MD00214D

Palladium-Catalyzed Cross-Coupling Reaction of Functionalized Aryl- and Heteroarylbismuthanes with 2-Halo(or 2-Triflyl)azines and -diazines

Pauline Petiot and Alexandre Gagnon

Eur. J. Org. Chem., 2013, 5282 DOI: 10.1002/ejoc.201300850

Tributyl(2-methoxyethynyl)stannane

Alexandre Gagnon

Encyclopedia of Reagents for Organic Synthesis (eROS), 2013 DOI: 10.1002/047084289.rn01539

2012

Inhibition of HIV-1 capsid assembly: Optimization of the antiviral potency by site selective modifications at N1, C2 and C16 of a 5-(5-furan-2-ylpyrazoly-1-yl)-1H-benzimidazole scaffold

Martin Tremblay, Pierre Bonneau, Yves Bousquet, Patrick DeRoy, Jianmin Duan, Martin Duplessis, Alexandre Gagnon, Michel Garneau, Nathalie Goudreau, Ingrid Guse, Oliver Hucke, Stephen H. Kawai, Christopher T. Lemke, Stephen W. Mason, Bruno Simoneau, Simon Surprenant, Steve Titolo, Christiane Yoakim

Bioorg. Med. Chem. Lett., 2012, 22, 7512 DOI: 10.1016/j.bmcl.2012.10.034

Highly Enantioselective Synthesis of 1,2,3-Substituted Cyclopropanes by Using α-Iodo and α-Chloromethylzinc Carbenoids

Louis-Philippe B. Beaulieu, Lucie E. Zimmer, Alexandre Gagnon and André B. Charette

Chem. Eur. J., 2012, 14784 DOI: 10.1002/chem.201202528

Distinct effects of two HIV-1 capsid assembly inhibitor families that bind the same site within the N-terminal domain of the viral CA protein

Christopher Lemke, Steve Titolo, Uta von Schwedler, Nathalie Goudreau, Jean-François Mercier, Elizabeth Wardrop, Anne-Marie Faucher, René Coulombe, Soma S. R. Banik, Lee Fader, Alexandre Gagnon, Stephen H. Kawai, Jean Rancourt, Martin Tremblay, Christiane Yoakim, Bruno Simoneau, Jacques Archambault, Wesley I. Sundquist and Stephen W. Mason

J. Virol., 2012, 86, 6643 DOI: 10.1128/JVI.00493-12

2011

Tricyclopropylbismuth

Alexandre Gagnon

Encyclopedia of Reagents for Organic Synthesis (Online), 2011, www.mrw.interscience.willey.com/eros/, 15 mars 2011 DOI: 10.1002/047084289X.m01272

Discovery of a 1,5-Dihydrobenzo[b][1,4]diazepine-2,4-dione Series of Inhibitors of HIV-1 Capsid Assembly

Lee Fader,* Richard Bethell, Pierre Bonneau, Michael Bös, Yves Bousquet, Michael G. Cordingley, René Coulombe, Patrick Deroy, Anne-Marie Faucher, Alexandre Gagnon, Nathalie Goudreau, Chantal Grand-Maître, Ingrid Guse, Oliver Hucke, Stephen H. Kawai, Jean-Eric Lacoste, Serge Landry, Christopher T. Lemke, Eric Malenfant, Stephen Mason, Sébastien Morin, Jeff O’Meara, Bruno Simoneau, Steve Titolo and Christiane Yoakim

Bioorg. Med. Chem. Lett., 2011, 21, 398 DOI: 10.1016/j.bmcl.2010.10.131

2010

Csp3-Csp2 Palladium-Catalyzed Cross-Coupling Reaction of Trialkylbismuth Reagents With Aryl, Heteroaryl, and Vinyl Halides and Triflates

Alexandre Gagnon,* Vincent Albert and Martin Duplessis

Synlett, 2010, 19, 2936 DOI: 10.1055/s-0030-1259023

Arylcyclopropanes: Properties, Synthesis and use in Medicinal Chemistry

Alexandre Gagnon,* Martin Duplessis and Lee Fader

Org. Prep. Proc. Int., Invited Review, 2010, 42, 1–69 DOI: 10.1080/00304940903507788

2009

Investigation on the role of the tetrazole in the binding of thiotetrazolylacetanilides with HIV-1 wild type and K103N/Y181C double mutant reverse transcriptases

Alexandre Gagnon,* Serge Landry, René Coulombe, Araz Jakalian, Ingrid Guse, Bounhkham Thavonekham, Pierre R. Bonneau, Christiane Yoakim and Bruno Simoneau

Bioorg. Med. Chem. Lett. 2009, 19, 1199 DOI: 10.1016/j.bmcl.2008.12.074

2008

Palladium-catalyzed cross-coupling reaction of tricyclopropylbismuth with aryl halides and triflates

Alexandre Gagnon,* Martin Duplessis, Pamela Alsabeh and Francis Barabé

J. Org. Chem., 2008, 73, 3604 (Highlighted in Synfacts 2008, 7, 744)

DOI: 10.1021/jo702377h

2007

Thiotetrazole alkynylacetanilides as potent and bioavailable non-nucleoside inhibitors of the HIV-1 wild-type and K103N/Y181C double mutant reverse transcriptases

Alexandre Gagnon,* Ma’an H. Amad, Pierre R. Bonneau, René Coulombe, Patrick L. DeRoy, Louise Doyon, Jianmin Duan, Michel Garneau, Ingrid Guse, Araz Jakalian, Eric Jolicoeur, Serge Landry, Eric Malenfant, Bruno Simoneau and Christiane Yoakim

Bioorg. Med. Chem. Lett. 2007, 17, 4437 DOI: 10.1016/j.bmcl.2007.06.012

Direct N-cyclopropylation of cyclic amides and azoles employing a cyclopropylbismuth reagent

Alexandre Gagnon,* Miguel St-Onge, Kelly Little, Martin Duplessis, Francis Barabé

J. Am. Chem. Soc. 2007, 129, 44 (Highlighted in Synfacts 2007, 3, 302) DOI: 10.1021/ja0676758

2006

Toward the synthesis of Xestocyclamine A: Investigation on the double-Michael reaction and direct aza Diels-Alder reaction

Heedong Yun, Alexandre Gagnon and Samuel J. Danishefsky

Tetrahedron Lett. 2006, 47, 5311 DOI: 10.1016/j.tetlet.2006.05.126

2002

Evaluation of diene hierarchies for Diels-Alder reactions en route to Xestocyclamine A: elaboration of the ansa bridge by B-Alkyl Suzuki macrocyclization

Alexandre Gagnon and Samuel J. Danishefsky

Angew. Chem. Int. Ed. 2002, 41, 1581

DOI: 10.1002/1521-3773(20020503)41:9<1581::AID-ANIE1581>3.0.CO;2-F

First evidence for the formation of a geminal dizinc carbenoid: a highly stereoselective synthesis of 1,2,3-substituted cyclopropanes

André B. Charette,* Alexandre Gagnon and Jean-François Fournier

J. Am. Chem. Soc. 2002, 124, 386 DOI: 10.1021/ja017230d

2000

(Z)bis-μ-[1-(2-naphthylmethyloxy)propan-2-iminato-O,N:N]bis[bromobis(tetrahydrofuran-O)magnesium] ditoluene solvate

André B. Charette,* Alexandre Gagnon and Francine Bélanger-Gariépy

Acta Cryst. 2000, C56, 538 DOI: 10.1107/S0108270100001281

1999

The stereoselective cyclopropanation of chiral allylic alcohols using a chiral dioxaborolane ligand: A new route to anti-cyclopropylmethanol derivatives

André B. Charette,* Hélène Lebel and Alexandre Gagnon

Tetrahedron, 1999, 55, 8845 DOI: 10.1016/S0040-4020(99)00448-2