The Ultrasound-accelerated Synthesis of New 7- Aminocarbohydrate-isoquinoline-5,8-quinone Derivatives

The Ultrasound-accelerated Synthesis of New 7- Aminocarbohydrate-isoquinoline-5,8-quinone Derivatives

Silva, Wanderson Amaral da; Campos, Vinícius Rangel; Santos, Angela Cristina P. B. dos; Jordão, Alessandro K.; Ferreira, Vitor F.; Souza, Maria Cecília B. V. de; Cunha, Anna Claudia

Abstract:

The synthesis of aminoquinones and related compounds has attracted considerable attention, because they exhibit a wide spectrum of pharmaceutical activities including antitumor and antimalarial properties. Two general methods are available for the synthesis of aminoquinones: nucleophilic substitution reaction of halo-derivative quinones with amines and direct 1,4-type addition of amines to quinones, with or without Lewis acid conditions under ultrasonic irradiation. As part of an ongoing research program on the synthesis of new quinone derivatives and on the basis of our experience in the field of the use of carbohydrates in organic synthesis, we herein report an extension of the second approach which led to three novel isoquinoline-5,8-quinone derivatives 1a-c, possessing a carbohydrate chain at C-7position of the quinone ring.

The synthesis of aminoquinones and related compounds has attracted considerable attention, because they exhibit a wide spectrum of pharmaceutical activities including antitumor and antimalarial properties. Two general methods are available for the synthesis of aminoquinones: nucleophilic substitution reaction of halo-derivative quinones with amines and direct 1,4-type addition of amines to quinones, with or without Lewis acid conditions under ultrasonic irradiation. As part of an ongoing research program on the synthesis of new quinone derivatives and on the basis of our experience in the field of the use of carbohydrates in organic synthesis, we herein report an extension of the second approach which led to three novel isoquinoline-5,8-quinone derivatives 1a-c, possessing a carbohydrate chain at C-7position of the quinone ring.

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DOI: 10.5151/chempro-14bmos-R0253-2

Referências bibliográficas

• [1] 1 Franco, C. F. J.; Jordão, A. K.; Ferreira, V. F.; Pinto, A. C.; Souza, M. C. B. V.; Cunha, A. C. J. Braz. Chem. Soc., 2011, 22, 1, 187-193.
• [2] 2 Liu, B.; Ji, S. J., Synt. Commun., 2008, 38, 1201.
• [3] 3 Santos, F. C. ; Abreu, P.; Castro, H. C.; Cirne-Santos, C. C.; Giongo, V.; Barbosa, J. E.; V. ; Bou-Habib, D. C.; Silva, D. O.; Temerozo, J. R.; de Souza, T. M.; Cunha, A. C.; Rodrigues, C. R.; Ferreira, V. F.; Souza, M. C. B. V., Bioorg. Med. Chem. 2009, 17, 5476.
• [4] 4 Valderrama, J. A.; Ibacache, J. A.; Arancibia, V.; Rodriguez, J.;Theoduloz, C., Bioor. Med. Chem., 2009, 17, 2894-2901.
• [5] 5 Cunha, A. C.; Pereira, L. O. R. ; Souza, R. O. P. ; Souza, M. C. B. V.; Ferreira, V. F., Nucleosides, Nucleotides Nucleic Acids, 2001, 20, 1555 .

Como citar:

Silva, Wanderson Amaral da; Campos, Vinícius Rangel; Santos, Angela Cristina P. B. dos; Jordão, Alessandro K.; Ferreira, Vitor F.; Souza, Maria Cecília B. V. de; Cunha, Anna Claudia; "The Ultrasound-accelerated Synthesis of New 7- Aminocarbohydrate-isoquinoline-5,8-quinone Derivatives", p-253-254. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0253-2