title: Studies on Quinones. Part 38: synthesis and leishmanicidal activity of sesquiterpene 1,4-Quinones.
abstract: The reaction of (+)-euryfuran 1 with several benzo-, naphtho- and benzo[b]thiophene-1,4-quinones in acetic acid yields the corresponding euryfuryl-1,4-quinones 3, 5, 7, 8, 10, 12, and 14. The structure of compounds 7, 8, 12, and 14 was assigned through 2D NMR 1H-13C HMBC experiments. The influence of the acidity of the solvent upon the reactivity and regioselectivity of the quinones to the oxidative coupling reaction, is discussed. The in vitro activity of the euryfurylquinones and their corresponding precursors against Leishmania amazonensis is described.
authors.affiliation: Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago-22, Chile. jvalderr@puc.cl
authors.forename: Jaime A
authors.initials: JA
authors.lastname: Valderrama
authors.forename: Julio
authors.initials: J
authors.lastname: Benites
authors.forename: Manuel
authors.initials: M
authors.lastname: Cortés
authors.forename: Hernán
authors.initials: H
authors.lastname: Pessoa-Mahana
authors.forename: Eric
authors.initials: E
authors.lastname: Prina
authors.forename: Alain
authors.initials: A
authors.lastname: Fournet
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007894:Leishmania mexicana / Q000187:drug effects*; D008264:Macrophages / Q000469:parasitology; D051379:Mice; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D012717:Sesquiterpenes / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000981:Antiprotozoal Agents; D011809:Quinones; D012717:Sesquiterpenes