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Research Article

Synthesis of new 4-(E)-alkenylpyrrolo[1,2-a]quinoxalines as antileishmanial agents by Suzuki-Miyaura cross-coupling reactions

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Pages 541-549 | Received 18 Oct 2006, Accepted 08 Feb 2007, Published online: 04 Oct 2008

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Jean Guillon, Anita Cohen, Clotilde Boudot, Alessandra Valle, Vittoria Milano, Rabindra Nath Das, Aurore Guédin, Stéphane Moreau, Luisa Ronga, Solène Savrimoutou, Maxime Demourgues, Elodie Reviriego, Sandra Rubio, Sandie Ferriez, Patrice Agnamey, Cécile Pauc, Serge Moukha, Pascale Dozolme, Sophie Da Nascimento, Pierre Laumaillé, Anne Bouchut, Nadine Azas, Jean-Louis Mergny, Catherine Mullié, Pascal Sonnet & Bertrand Courtioux. (2020) Design, synthesis, and antiprotozoal evaluation of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry 35:1, pages 432-459.
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Jean Guillon, Anita Cohen, Nassima Meriem Gueddouda, Rabindra Nath Das, Stéphane Moreau, Luisa Ronga, Solène Savrimoutou, Louise Basmaciyan, Alix Monnier, Myriam Monget, Sandra Rubio, Timothée Garnerin, Nadine Azas, Jean-Louis Mergny, Catherine Mullié & Pascal Sonnet. (2017) Design, synthesis and antimalarial activity of novel bis{N-[(pyrrolo[1,2-a]quinoxalin-4-yl)benzyl]-3-aminopropyl}amine derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry 32:1, pages 547-563.
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Vanessa Desplat, Stéphane Moreau, Solene Belisle-Fabre, Denis Thiolat, Juliette Uranga, Romain Lucas, Laure de Moor, Stéphane Massip, Christian Jarry, Djavad M. Mossalayi, Pascal Sonnet, Gérard Déléris & Jean Guillon. (2011) Synthesis and evaluation of the antiproliferative activity of novel isoindolo[2,1-a]quinoxaline and indolo[1,2-a]quinoxaline derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry 26:5, pages 657-667.
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Vanessa Desplat, Stephane Moreau, Aurore Gay, Solene Belisle Fabre, Denis Thiolat, Stephane Massip, Gregory Macky, Frederic Godde, Djavad Mossalayi, Christian Jarry & Jean Guillon. (2010) Synthesis and evaluation of the antiproliferative activity of novel pyrrolo[1,2-a]quinoxaline derivatives, potential inhibitors of Akt kinase. Part II. Journal of Enzyme Inhibition and Medicinal Chemistry 25:2, pages 204-215.
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Vanessa Desplat, Ambre Geneste, Marc-Antoine Begorre, Solene Belisle Fabre, Stephane Brajot, Stephane Massip, Denis Thiolat, Djavad Mossalayi, Christian Jarry & Jean Guillon. (2008) Synthesis of New Pyrrolo[1,2-a]quinoxaline Derivatives as Potential Inhibitors of Akt Kinase. Journal of Enzyme Inhibition and Medicinal Chemistry 23:5, pages 648-658.
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Simone C. B. Gnoatto, Luciana Dalla Vechia, Claiton L. Lencina, Alexandra Dassonville-Klimpt, Sophie Da Nascimento, Djavad Mossalayi, Jean Guillon, Grace Gosmann & Pascal Sonnet. (2008) Synthesis and preliminary evaluation of new ursolic and oleanolic acids derivatives as antileishmanial agents. Journal of Enzyme Inhibition and Medicinal Chemistry 23:5, pages 604-610.
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Articles from other publishers (23)

Jean Guillon, Solène Savrimoutou, Sandra Albenque-Rubio, Noël Pinaud, Nina Fillová, Stéphane Moreau, Virginie Baylot & Vanessa Desplat. (2023) Synthesis, Crystal Structure and Anti-Leukemic Activity of (E)-Pyrrolo[1,2-a]quinoxalin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one. Molbank 2023:3, pages M1691.
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Yufei Song, Zhaolin Quan, Zhengkai Chen & Xiao-Feng Wu. (2023) Carbonylative Synthesis of Fused Quinoxalinones via Palladium-Catalyzed Cascade Cyclization of 2-Heteroaryl Iodobenzene and NaN 3 . Organic Letters 25:21, pages 3984-3988.
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Dalavai Pavithra, Kannat Radhakrishnan Ethiraj & Fazlur‐Rahman Nawaz Khan. (2020) Cu‐TEMPO Catalyzed Dehydrogenative Friedlander Annulation/sp 3 C–H Functionalization/Spiroannulation towards Spiro[indoline‐3,3'‐pyrrolizin]‐2'‐yl)‐4‐phenylquinoline‐3‐Carboxylates . European Journal of Organic Chemistry 2020:45, pages 7035-7050.
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Soda Prameela & Fazlur-Rahman Nawaz Khan. (2020) Ru-Catalyzed Sequential Dehydrogenative Friedlander Reaction/sp 3 C-H Activation/Knovenagel Condensation in the Regioselective Synthesis of Chimanine B Analogues . European Journal of Organic Chemistry 2020:19, pages 2888-2903.
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Jean Guillon, Shweta Nim, Stéphane Moreau, Luisa Ronga, Solène Savrimoutou, Elisabeth Thivet, Mathieu Marchivie, Attilio Di Pietro, Rajendra Prasad & Marc Le Borgne. (2020) Synthesis of new piperazinyl-pyrrolo[1,2- a ]quinoxaline derivatives as inhibitors of Candida albicans multidrug transporters by a Buchwald–Hartwig cross-coupling reaction . RSC Advances 10:5, pages 2915-2931.
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Sneha H. Meshram, Tungana Ramesh, Jagadeesh Babu Nanubolu, Ajay Kumar Srivastava, Bhaskar Rao Adari & Nivedita Sahu. (2019) Green synthesis of enantiopure quinoxaline alcohols using Daucus carota . Chirality 31:4, pages 312-320.
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Dandugudumula Ramu, Ravi Jain, Ravi R. Kumar, Veena Sharma, Swati Garg, Rajagopal Ayana, Tania Luthra, Preeti Yadav, Subhabrata Sen & Shailja Singh. (2019) Design and synthesis of imidazolidinone derivatives as potent anti‐leishmanial agents by bioisosterism. Archiv der Pharmazie 352:4, pages 1800290.
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Jean Guillon, Anita Cohen, Rabindra Nath Das, Clotilde Boudot, Nassima Meriem Gueddouda, Stéphane Moreau, Luisa Ronga, Solène Savrimoutou, Louise Basmaciyan, Camille Tisnerat, Sacha Mestanier, Sandra Rubio, Sophia Amaziane, Alexandra Dassonville-Klimpt, Nadine Azas, Bertrand Courtioux, Jean-Louis Mergny, Catherine Mullié & Pascal Sonnet. (2018) Design, synthesis, and antiprotozoal evaluation of new 2,9-bis[(substituted-aminomethyl)phenyl]-1,10-phenanthroline derivatives. Chemical Biology & Drug Design 91:5, pages 974-995.
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Karla Fabiola Chacón-Vargas, Sergio Andrade-Ochoa, Benjamín Nogueda-Torres, Dulce Carolina Juárez-Ramírez, Edgar E. Lara-Ramírez, Ricardo Mondragón-Flores, Antonio Monge, Gildardo Rivera & Luvia Enid Sánchez-Torres. (2017) Isopropyl quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives induce regulated necrosis-like cell death on Leishmania (Leishmania) mexicana. Parasitology Research 117:1, pages 45-58.
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Vanessa Desplat, Marian Vincenzi, Romain Lucas, Stéphane Moreau, Solène Savrimoutou, Noël Pinaud, Jordi Lesbordes, Elodie Peyrilles, Mathieu Marchivie, Sylvain Routier, Pascal Sonnet, Filomena Rossi, Luisa Ronga & Jean Guillon. (2016) Synthesis and evaluation of the cytotoxic activity of novel ethyl 4-[4-(4-substitutedpiperidin-1-yl)]benzyl-phenylpyrrolo[1,2-a]quinoxaline-carboxylate derivatives in myeloid and lymphoid leukemia cell lines. European Journal of Medicinal Chemistry 113, pages 214-227.
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Vakhid A. MamedovVakhid A. Mamedov. 2016. Quinoxalines. Quinoxalines 135 210 .
Hidayat Hussain, Ahmed Al-Harrasi, Ahmed Al-Rawahi, Ivan R. Green & Simon Gibbons. (2014) Fruitful Decade for Antileishmanial Compounds from 2002 to Late 2011. Chemical Reviews 114:20, pages 10369-10428.
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Luisa Ronga, Marco Del Favero, Anita Cohen, Claire Soum, Patrice Le Pape, Solène Savrimoutou, Noël Pinaud, Catherine Mullié, Sylvie Daulouede, Philippe Vincendeau, Natacha Farvacques, Patrice Agnamey, Fabrice Pagniez, Sébastien Hutter, Nadine Azas, Pascal Sonnet & Jean Guillon. (2014) Design, synthesis and biological evaluation of novel 4-alkapolyenylpyrrolo[1,2-a]quinoxalines as antileishmanial agents – Part III. European Journal of Medicinal Chemistry 81, pages 378-393.
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Jean Guillon, Marc Le Borgne, Charlotte Rimbault, Stéphane Moreau, Solène Savrimoutou, Noël Pinaud, Sophie Baratin, Mathieu Marchivie, Séverine Roche, Andre Bollacke, Adali Pecci, Lautaro Alvarez, Vanessa Desplat & Joachim Jose. (2013) Synthesis and biological evaluation of novel substituted pyrrolo[1,2-a]quinoxaline derivatives as inhibitors of the human protein kinase CK2. European Journal of Medicinal Chemistry 65, pages 205-222.
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Juan C. Castillo, Rodrigo Abonía, Justo Cobo & Christopher Glidewell. (2013) A chain of π-stacked molecules in 4-(2-chlorophenyl)pyrrolo[1,2- a ]quinoxaline and a hydrogen-bonded sheet in (4 RS )-4-(1,3-1,3-benzodioxol-6-yl)-4,5-dihydropyrrolo[1,2- a ]quinoxaline . Acta Crystallographica Section C Crystal Structure Communications 69:5, pages 544-548.
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Gary A. Molander & Ludivine Jean-Gérard. 2004. Organic Reactions. Organic Reactions 1 316 .
Jean Guillon, Elisabeth Mouray, Stéphane Moreau, Catherine Mullié, Isabelle Forfar, Vanessa Desplat, Solene Belisle-Fabre, Noël Pinaud, François Ravanello, Augustin Le-Naour, Jean-Michel Léger, Grace Gosmann, Christian Jarry, Gérard Déléris, Pascal Sonnet & Philippe Grellier. (2011) New ferrocenic pyrrolo[1,2-a]quinoxaline derivatives: Synthesis, and in vitro antimalarial activity – Part II. European Journal of Medicinal Chemistry 46:6, pages 2310-2326.
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A. A. Kalinin & V. A. Mamedov. (2011) Pyrrolo[1,2-a]quinoxalines based on pyrroles (Review). Chemistry of Heterocyclic Compounds 46:12, pages 1423-1442.
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Alexia Jonet, Alexandra Dassonville-Klimpt, Sophie Da Nascimento, Jean-Michel Leger, Jean Guillon & Pascal Sonnet. (2011) First enantioselective synthesis of 4-aminoalcohol quinoline derivatives through a regioselective SN2 epoxide opening mechanism. Tetrahedron: Asymmetry 22:2, pages 138-148.
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Juan C. Castillo, Rodrigo Abonía, Justo Cobo & Christopher Glidewell. (2010) Pseudomerohedral twinning, pseudosymmetry and complex hydrogen-bonded sheets in 2-methoxy-4-(pyrrolo[1,2- a ]quinoxalin-4-yl)phenol . Acta Crystallographica Section C Crystal Structure Communications 66:8, pages o385-o388.
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Jean GUILLON, Solàne BELISLE FABRE, Vanessa DESPLAT, Jean-Michel LEGER, Isabelle FORFAR & Christian JARRY. (2009) Second Polymorph of 7-Methoxy-4-[(E)-oct-1-enyl]pyrrolo[1,2-a]quinoxaline. X-ray Structure Analysis Online 25, pages 109-110.
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Jean Guillon, Stéphane Moreau, Elisabeth Mouray, Véronique Sinou, Isabelle Forfar, Solene Belisle Fabre, Vanessa Desplat, Pascal Millet, Daniel Parzy, Christian Jarry & Philippe Grellier. (2008) New ferrocenic pyrrolo[1,2-a]quinoxaline derivatives: Synthesis, and in vitro antimalarial activity. Bioorganic & Medicinal Chemistry 16:20, pages 9133-9144.
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Jean GUILLON, Isabelle FORFAR, Vanessa DESPLAT, Solène BELISLE FABRE, Stéphane MASSIP, Djavad MOSSALAYI & Christian JARRY. (2008) Crystal Structure of 7-Methoxy-4-[(E)-oct-1-enyl]pyrrolo[1,2-a]quinoxaline. Analytical Sciences: X-ray Structure Analysis Online 24, pages X35-X36.
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