2. Academic Validation
  3. Design, synthesis and biological evaluation of novel 4-alkapolyenylpyrrolo[1,2-a]quinoxalines as antileishmanial agents--part III

Design, synthesis and biological evaluation of novel 4-alkapolyenylpyrrolo[1,2-a]quinoxalines as antileishmanial agents--part III

  • Eur J Med Chem. 2014 Jun 23:81:378-93. doi: 10.1016/j.ejmech.2014.05.037.
Luisa Ronga 1,  Marco Del Favero 1,  Anita Cohen 2,  Claire Soum 1,  Patrice Le Pape 3,  Solène Savrimoutou 1,  Noël Pinaud 4,  Catherine Mullié 5,  Sylvie Daulouede 6,  Philippe Vincendeau 6,  Natacha Farvacques 5,  Patrice Agnamey 7,  Fabrice Pagniez 3,  Sébastien Hutter 2,  Nadine Azas 2,  Pascal Sonnet 5,  Jean Guillon 8
Affiliations

Affiliations

  • 1 Univ. Bordeaux, UFR des Sciences Pharmaceutiques, ARNA Laboratory, F-33076 Bordeaux Cedex, France; INSERM U869, ARNA Laboratory, F-33000 Bordeaux, France.
  • 2 Aix-Marseille Univ., Laboratory of Parasitology, UMR-MD3, Faculty of Pharmacy, 27 Bd Jean Moulin, CS30064, F-13385 Marseille Cedex 5, France.
  • 3 Université de Nantes, Département de Parasitologie et Mycologie Médicale, IICiMed, EA1155, UFR des Sciences Pharmaceutiques, F-44000 Nantes, France.
  • 4 Univ. Bordeaux, ISM - CNRS UMR 5255, 351 cours de la Libération, F-33405 Talence Cedex, France.
  • 5 Université de Picardie Jules Verne, Laboratoire de Glycochimie, des Antimicrobiens et des Agroressouces, CNRS FRE 3517, UFR de Pharmacie, 1 Rue des Louvels, F-80037 Amiens Cedex 01, France.
  • 6 UMR 177 IRD CIRAD, Université de Bordeaux, Laboratoire de Parasitologie, F-33076 Bordeaux Cedex, France.
  • 7 Université de Picardie Jules Verne, Laboratoire de Glycochimie, des Antimicrobiens et des Agroressouces, CNRS FRE 3517, UFR de Pharmacie, 1 Rue des Louvels, F-80037 Amiens Cedex 01, France; CHU Amiens, Laboratoire de Parasitologie-Mycologie, Avenue Laënnec, 80054 Amiens, France.
  • 8 Univ. Bordeaux, UFR des Sciences Pharmaceutiques, ARNA Laboratory, F-33076 Bordeaux Cedex, France; INSERM U869, ARNA Laboratory, F-33000 Bordeaux, France. Electronic address: jean.guillon@u-bordeaux.fr.
PMID: 24858543 DOI: 10.1016/j.ejmech.2014.05.037
Abstract

A series of new 4-alkapolyenylpyrrolo[1,2-a]quinoxaline derivatives, original and structural analogues of alkaloid chimanine B and of previously described 4-alkenylpyrrolo[1,2-a]quinoxalines, was synthesized in good yields using efficient palladium-catalyzed Suzuki-Miyaura cross-coupling reactions. These new compounds were tested for in vitro antiparasitic activity upon three Leishmania spp. strains. Biological results showed activity against the promastigote forms of L. major, L. mexicana and L. donovani with IC50 ranging from 1.2 to 14.7 μM. In attempting to investigate if our pyrrolo[1,2-a]quinoxaline derivatives are broad-spectrum antiprotozoal compounds activities toward one Trypanosoma brucei brucei strain and the W2 and 3D7 Plasmodium falciparum strains were also investigated. In parallel, the in vitro cytotoxicity of these molecules was assessed on the murine J774 and human HepG2 cell lines. Structure-activity relationships of these new synthetic compounds are here discussed.

Keywords

Antileishmanial activity; Antimalarial activity; Antitrypanosomal activity; Pyrrolo[1,2-a]quinoxaline; Suzuki reaction; Synthesis.

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