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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 8, Issue 5, 2011

Page: [347 - 351] Pages: 5

DOI: 10.2174/157017811795685063

Price: $65

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.

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


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