Literature DB >> 21458112

New ferrocenic pyrrolo[1,2-a]quinoxaline derivatives: synthesis, and in vitro antimalarial activity--Part II.

Jean Guillon1, 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.   

Abstract

Following our search for antimalarial compounds, novel series of ferrocenyl-substituted pyrrolo[1,2-a]quinoxalines 1-2 were synthesized from ferrocene-carboxaldehyde and tested for their in vitro activity upon the erythrocytic development of Plasmodium falciparum strains with different chloroquine-resistance status. The ferrocenic pyrrolo[1,2-a]quinoxalines 1-2 were prepared in 6 or 9 steps through a Barton-Zard reaction. Promising pharmacological results against FcB1, K1 and F32 strains were obtained with ferrocenyl pyrrolo[1,2-a]quinoxalines 1j-l linked by a bis-(3-aminopropyl)piperazine linker substituted by a nitrobenzyl moiety.
Copyright © 2011 Elsevier Masson SAS. All rights reserved.

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Year:  2011        PMID: 21458112     DOI: 10.1016/j.ejmech.2011.03.014

Source DB:  PubMed          Journal:  Eur J Med Chem        ISSN: 0223-5234            Impact factor:   6.514


  9 in total

1.  A facile three- and four-component procedure toward the synthesis of functionalized pyrano- and benzo[f]quinoxaline derivatives.

Authors:  Rahim Ghadari; Fatemeh Hajishaabanha; Morteza Aghaei; Ahmad Shaabani; Seik Weng Ng
Journal:  Mol Divers       Date:  2012-06-24       Impact factor: 2.943

2.  One-pot sequential coupling reactions as a new practical protocol for the synthesis of unsymmetrical 2,3-diethynyl quinoxalines and 4-ethynyl-substituted pyrrolo[1,2-a]quinoxalines.

Authors:  Ali Keivanloo; Saeed Lashkari; Mohammad Bakherad; Mahsa Fakharian; Sima Abbaspour
Journal:  Mol Divers       Date:  2020-04-16       Impact factor: 2.943

3.  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.

Authors:  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
Journal:  J Enzyme Inhib Med Chem       Date:  2020-12       Impact factor: 5.051

4.  α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction.

Authors:  Mayavan Viji; Manjunatha Vishwanath; Jaeuk Sim; Yunjeong Park; Chanhyun Jung; Seohu Lee; Heesoon Lee; Kiho Lee; Jae-Kyung Jung
Journal:  RSC Adv       Date:  2020-10-07       Impact factor: 4.036

5.  Design, synthesis and antimalarial activity of novel bis{N-[(pyrrolo[1,2-a]quinoxalin-4-yl)benzyl]-3-aminopropyl}amine derivatives.

Authors:  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
Journal:  J Enzyme Inhib Med Chem       Date:  2017-12       Impact factor: 5.051

Review 6.  Ferrocene-Based Compounds with Antimalaria/Anticancer Activity.

Authors:  Sijongesonke Peter; Blessing Atim Aderibigbe
Journal:  Molecules       Date:  2019-10-07       Impact factor: 4.411

7.  I2-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot.

Authors:  Lingkai Kong; Jieru Meng; Wenyue Tian; Jiazheng Liu; Xueping Hu; Zhi-Hong Jiang; Wei Zhang; Yanzhong Li; Li-Ping Bai
Journal:  ACS Omega       Date:  2021-12-21

Review 8.  Recent advances in the transition-metal-free synthesis of quinoxalines.

Authors:  Biplob Borah; L Raju Chowhan
Journal:  RSC Adv       Date:  2021-11-19       Impact factor: 4.036

9.  First synthesis of meso-substituted pyrrolo[1,2-a]quinoxalinoporphyrins.

Authors:  Dileep Kumar Singh; Mahendra Nath
Journal:  Beilstein J Org Chem       Date:  2014-04-08       Impact factor: 2.883

  9 in total

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