title: Anti-leishmanial and structure-activity relationship of ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives.
abstract: A series of ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives were synthesized and tested for in vitro leishmanicidal activity against amastigotes of Leishmania amazonensis in axenical cultures and murine infected macrophages. Structure-activity relationships demonstrated the importance of a radical methoxy at position R3', R4' and R5'. (2E)-3-(3,4,5-trimethoxy-phenyl)-1-(3,6,7-trimethyl-1,4-dioxy-quinoxalin-2-yl)-propenone was the most active. Cytotoxicity on macrophages revealed that this product was almost six times more active than toxic.
authors.affiliation: Unidad de Investigación y Desarrollo de Medicamentos, Centro de Investigación en Farmacobiología Aplicada, University of Navarra, Campus Universitario, Pamplona, Spain.
authors.forename: Asunción
authors.initials: A
authors.lastname: Burguete
authors.forename: Yannick
authors.initials: Y
authors.lastname: Estevez
authors.forename: Denis
authors.initials: D
authors.lastname: Castillo
authors.forename: Germán
authors.initials: G
authors.lastname: González
authors.forename: Raquel
authors.initials: R
authors.lastname: Villar
authors.forename: Beatriz
authors.initials: B
authors.lastname: Solano
authors.forename: Esther
authors.initials: E
authors.lastname: Vicente
authors.forename: Silvia Pérez
authors.initials: SP
authors.lastname: Silanes
authors.forename: Ignacio
authors.initials: I
authors.lastname: Aldana
authors.forename: Antonio
authors.initials: A
authors.lastname: Monge
authors.forename: Michel
authors.initials: M
authors.lastname: Sauvain
authors.forename: Eric
authors.initials: E
authors.lastname: Deharo
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D003497:Cyclic N-Oxides / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D005260:Female; D007894:Leishmania mexicana / Q000187:drug effects*; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D008807:Mice, Inbred BALB C; D021261:Parasitic Sensitivity Tests; D011810:Quinoxalines / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D013329:Structure-Activity Relationship
chemical_list: D000981:Antiprotozoal Agents; D003497:Cyclic N-Oxides; D011810:Quinoxalines