Synthesis of naphthoxazole derivates from lapachol and their isolation by countercurrent chromatography

Synthesis of naphthoxazole derivates from lapachol and their isolation by countercurrent chromatography

Rio, Karina P. DeI; Leitão, Gilda G.; Moura., Kelly C. Gallan de

Abstract:

In recent years, a number of studies showed that the heterofunctionalization of the quinone structure of β-lapachone in the preparation of bioactive imidazoles and oxazoles were of great value in the treatment of Chagas`s disease. The use of other natural quinones, such as lapachol (1), in the synthesis of new heterocycles becomes important in the development of new bioactive substances, either in the combat of Chagas`s disease or in the treatment of other diseases. Silica gel column chromatography is the chromatographic method conventionally used for the purification of these derivates, however it consumes much time and large amounts of solvent. In order to improve the isolation procedure, high speed countercurrent chromatography was used instead.

In recent years, a number of studies showed that the heterofunctionalization of the quinone structure of β-lapachone in the preparation of bioactive imidazoles and oxazoles were of great value in the treatment of Chagas`s disease. The use of other natural quinones, such as lapachol (1), in the synthesis of new heterocycles becomes important in the development of new bioactive substances, either in the combat of Chagas`s disease or in the treatment of other diseases. Silica gel column chromatography is the chromatographic method conventionally used for the purification of these derivates, however it consumes much time and large amounts of solvent. In order to improve the isolation procedure, high speed countercurrent chromatography was used instead.

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DOI: 10.5151/chempro-15bmos-BMOS2013_201381611490

Referências bibliográficas

• [1] 1 de Moura, K.C.G., Emery, F.S., Pinto, C.N., Pinto, M.C.F.R., Dantas, A.P., Salomão, K., de Castro, S.L., Pinto, A.V. J. Braz. Chem. Soc. 2001, 12, 325-338.
• [2] 2 de Moura, K.C.G., Salomão, K., Menna-Barreto, R.F.S., Emery, F.S., Pinto, M.C.F.R., Pinto, A.V., Castro, S.L, Eur. J. Med. Chem. 2004, 39, 639-645.
• [3] 3 Silva, R. S. F.; Leitão, G. G.; Brum, T. B.; Lobato, A. P. G.; Pinto, M. C. F. R.; Pinto, A. V. J. Chromatogr. A. 2007, 1151, 197.

Como citar:

Rio, Karina P. DeI; Leitão, Gilda G.; Moura., Kelly C. Gallan de; "Synthesis of naphthoxazole derivates from lapachol and their isolation by countercurrent chromatography", p-39-39. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201381611490