Utilize este identificador para referenciar este registo: http://hdl.handle.net/10451/21278
Título: Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine
scope and limitations
Autor: Gomes, P
Araujo, MJ
Rodrigues, M
Vale, N
Azevedo, Z
Iley, J
Chambel, P
Morais, J
Moreira, R
Palavras-chave: Chemistry, Organic
Data: 2004
Editora: PERGAMON-ELSEVIER SCIENCE LTD
Citação: TETRAHEDRON. - Vol. 60, n. 26 (2004), p. 5551-5562
Resumo: The synthesis of imidazolidin-4-one derivatives of primaquine as potential antimalarial agents is described. The target compounds were synthesized in three steps: (i) condensation of (+/-)-primaquine with N-alpha-protected amino acids, (ii) removal of the N-alpha-protecting group, and (iii) reaction of the N-acylprimaquine with a carbonyl compound: acetone, three cyclic ketones and veratraldehyde. Using 2-formylbenzoic acid in the third step afforded 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-diones. All products were isolated in good to excellent yields. Whereas imidazolidin-4-ones were formed as mixtures of all possible diastereomers in equal amounts, 1H-imidazo[2,1a]isoindole-2,5(3H,9bH)-diones were produced in a stereoselective fashion. The compounds hydrolyse very Slowly (t(1/2) 5-30 d) in pH 7.4 buffer to release primaquine. These primaquine derivatives are being submitted to biological assays, and preliminary results of their antimalarial activity are quite encouraging. (C) 2004 Elsevier Ltd. All rights reserved.
URI: http://hdl.handle.net/10451/21278
DOI: http://dx.doi.org/10.1016/j.tet.2004.04.077
ISSN: 0040-4020
Aparece nas colecções:FF - Produção Científica 2000-2009

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