Natural Furano Naphtoquinones from Lapachol: Hydroxyiso-β -Lapachone, Stenocarpoquinone-B and Avicequinone-C

Title: Natural Furano Naphtoquinones from Lapachol: Hydroxyiso-β -Lapachone, Stenocarpoquinone-B and Avicequinone-C

Volume: 8 Issue: 5

Author(s): Carlos Magno R. Ribeiro, Pablo P. de Souza, L. D.M. Ferreira, Sharlene L. Pereira, Ingrid da S. Martins, Rosangela de A. Epifanio, Leticia V. Costa-Lotufo, Paula C. Jimenez, Claudia Pessoa and Manoel O. de Moraes

Affiliation:

Keywords: Lapachol, natural naphthoquinones, cyclization reactions, anticancer, antibacterial, antimalarial, antifungal, antileishmanial, molluscicidal, antivirus

Abstract: This work describes cheap and simple methods to obtain biological active furano naphthoquinones in good yields. Hydroxyiso-β-lapachone (3) was obtained in 61% yield from the reaction of lapachol (1) and MCPBA in dichloromethane using Na2HPO4 as the base. Reaction of 1 with MCPBA, followed by the addition of KOH/DMSO furnished both stenocarpoquinone-A (2) and avicequinone-C (5) in 20% yield. Using oxone/acetone and NaHCO3, stenocarpoquinone-B (4) was obtained in 50% yield. The biological assays using tumor cell lines showed that 1 is, in general, less toxic than its derivatives. Compounds 4 and 5, on the other hand, were strongly active against the four tested tumor cells.

Cite this article as:

Magno R. Ribeiro Carlos, P. de Souza Pablo, D.M. Ferreira L., L. Pereira Sharlene, da S. Martins Ingrid, de A. Epifanio Rosangela, V. Costa-Lotufo Leticia, C. Jimenez Paula, Pessoa Claudia and O. de Moraes Manoel, Natural Furano Naphtoquinones from Lapachol: Hydroxyiso-β -Lapachone, Stenocarpoquinone-B and Avicequinone-C, Letters in Organic Chemistry 2011; 8 (5) . https://dx.doi.org/10.2174/157017811795685063