title: In vivo antimalarial activity of novel 2-hydroxy-3-anilino-1,4-naphthoquinones obtained by epoxide ring-opening reaction.
abstract: 1,4-Naphthoquinone derivatives are known to have relevant activities against several parasites. Among the treatment options for malaria, atovaquone, a 1,4-naphthoquinone derivative, is widely applied in the treatment and prophylaxis of such disease. Based on the structure simplification of atovaquone, we designed and synthesized four novel naphthoquinoidal derivatives. The compounds were obtained by the underexplored epoxide-opening reaction of 1,4-naphthoquinone using aniline derivatives as nucleophiles. The antiplasmodial activity of the synthesized compounds was performed in vivo using Peter's 4days suppression test. Significant parasitemia reduction and increased survival were observed for some of the compounds.
authors.affiliation: Departamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, 14040-903 Ribeirão Preto-SP, Brazil.
authors.forename: Lucas Cunha Dias
authors.initials: LC
authors.lastname: de Rezende
authors.forename: Fernando
authors.initials: F
authors.lastname: Fumagalli
authors.forename: Marraiana Schiavon
authors.initials: MS
authors.lastname: Bortolin
authors.forename: Marianne Garcia
authors.initials: MG
authors.lastname: de Oliveira
authors.forename: Murilo Helder
authors.initials: MH
authors.lastname: de Paula
authors.forename: Valter Ferreira
authors.initials: VF
authors.lastname: de Andrade-Neto
authors.forename: Flavio da Silva
authors.initials: Fda S
authors.lastname: Emery
mesh_terms: D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004852:Epoxy Compounds / Q000737:chemistry*; D008288:Malaria / Q000188:drug therapy; D051379:Mice; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010963:Plasmodium falciparum / Q000187:drug effects*; D016019:Survival Analysis
chemical_list: D000962:Antimalarials; D004852:Epoxy Compounds; D009285:Naphthoquinones; C035342:1,4-naphthoquinone
keywords: Anilines; Epoxides; Naphthoquinones; Plasmodium; Ring-opening