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, Manoel O. de Moraes.

Journal Name: Letters in Organic Chemistry

Volume 8 , Issue 5 , 2011

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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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Article Details

VOLUME: 8
ISSUE: 5
Year: 2011
Page: [347 - 351]
Pages: 5
DOI: 10.2174/157017811795685063
Price: $58

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