In vivo antimalarial activity of novel 2-hydroxy-3-anilino-1,4-naphthoquinones obtained by epoxide ring-opening reaction

Author(s)

Dias de Rezende, Lucas Cunha ^[1] ; Fumagalli, Fernando ^[1] ; Bortolin, Marraiana Schiavon ^[1] ; de Oliveira, Marianne Garcia ^[2] ; de Paula, Murilo Helder ^[1] ; de Andrade-Neto, Valter Ferreira ^[2] ; Emery, Flavio da Silva ^[1]

Affiliation

^[1] Univ Sao Paulo, Dept Ciencias Farmaceut, Fac Ciencias Farmaceut Ribeirao Preto, BR-14040903 Ribeirao Preto, SP - Brazil

^[2] Univ Fed Rio Grande do Norte, Dept Microbiol & Parasitol, Ctr Biociencias, Lab Biol Malaria & Toxoplasmose, BR-59000000 Natal, RN - Brazil

• Document type: Journal article
• Source: Bioorganic & Medicinal Chemistry Letters; v. 23, n. 16, p. 4583-4586, AUG 15 2013.
• Web of Science Citations: 17

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 4 days suppression test. Significant parasitemia reduction and increased survival were observed for some of the compounds. (C) 2013 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 09/14184-0 - Antiinfective compounds: bringing together medicinal chemistry and organic synthesis in search of lead antiparasitic compounds
• Grantee: Flavio da Silva Emery
• Support Opportunities: Regular Research Grants