Synthesis of Lapachol Analogues through Suzuki-Miyaura Cross-Coupling. Antitumoral Evaluation.

Synthesis of Lapachol Analogues through Suzuki-Miyaura Cross-Coupling. Antitumoral Evaluation.

Gomes, S. L. S.; Costa, A. M.; Militão, G. C. G.; Costa, P. R. R.1; da Silva, A. J. M.

Abstract:

Lapachol (Figure 1) is a naphtoquinone extracted from the bark of Pau d`Arco. This compound presents antineoplasic activity that is associated to the DNA repair inhibition and also acts as an oxidation and phosphorylation inhibitor in the mitochondria. It is believed that the presence of the prenyl group is important to the observed activity. Recently, the molluscicidal, antimalarial, antitrypanosomal and antiviral activities of lapachol and analogues have been reported.

Lapachol (Figure 1) is a naphtoquinone extracted from the bark of Pau d`Arco. This compound presents antineoplasic activity that is associated to the DNA repair inhibition and also acts as an oxidation and phosphorylation inhibitor in the mitochondria. It is believed that the presence of the prenyl group is important to the observed activity. Recently, the molluscicidal, antimalarial, antitrypanosomal and antiviral activities of lapachol and analogues have been reported.

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DOI: 10.5151/chempro-14bmos-R0034-1

Referências bibliográficas

• [1] 1 Hussain, H.; Krohn, K.; Ahmad, V. U.; Miana, G. A.; Green, I. R.; ARKIVOC 2007 (ii), 145.
• [2] 2 L. C. R. M.; Canavez, R. C. P.; Gomes, S. L. S.; da Silva, A. J. M.; Costa, P. R. R.; J. Braz. Chem. Soc. 2009, 1916.
• [3] 3a Suzuki, A.; J. Organomet. Chem. 2002, 653, 83. 3b Watanabe, T.; Miyaura, N.; Suzuki, A.; Synlett 1992, 207. , 3c Pousse, G.; Devineau, A.; Dalla, V.; Humphreys, L.; Lasne, M. C.; Rouden, J.; Blanchet, J.; Tetrahedron 2009, 10617.
• [4] 4 Greene, T. W.; Wuts, P. G. M.; Protective Groups in Organic Synthesis 4th edition, John Wiley And Sons, INC, 2007.

Como citar:

Gomes, S. L. S.; Costa, A. M.; Militão, G. C. G.; Costa, P. R. R.1; da Silva, A. J. M.; "Synthesis of Lapachol Analogues through Suzuki-Miyaura Cross-Coupling. Antitumoral Evaluation.", p-34-34. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0034-1