Studies on Quinones. Part 38: synthesis and leishmanicidal activity of sesquiterpene 1,4-Quinones.
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.
Valderrama
Jaime A
JA
Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago-22, Chile. jvalderr@puc.cl
Benites
Julio
J
Cortés
Manuel
M
Pessoa-Mahana
Hernán
H
Prina
Eric
E
Fournet
Alain
A
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
D000981:Antiprotozoal Agents; D011809:Quinones; D012717:Sesquiterpenes