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Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine: scope and limitations

Gomes, Paula; Araújo, Maria J.; Rodrigues, Manuela; Vale, Nuno; Azevedo, Zelia; Iley, Jim; Chambel, Paula; Morais, Jose and Moreira, Rui (2004). Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine: scope and limitations. Tetrahedron, 60(26) pp. 5551–5562.

DOI (Digital Object Identifier) Link: http://dx.doi.org/10.1016/j.tet.2004.04.077
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Abstract

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 Na-protected amino acids, (ii) removal of the Naprotecting 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[2,1-
a]isoindole-2,5(3H,9bH)-diones were produced in a stereoselective fashion. The compounds hydrolyse very slowly (t1/2 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.

Item Type: Journal Article
ISSN: 0040-4020
Extra Information: Some of the symbols may not have transferred correctly into this bibliographic record.
Keywords: malaria; imidazolidinones; primaquine; Mannich bases; antimalarial; Imidazolidin-4-one; 1H-Imidazo[2,1-a]isoindole-2; 5(3H,9bH)-diones; Primaquine; stereoselectivity
Academic Unit/Department: Science > Life, Health and Chemical Sciences
Item ID: 3994
Depositing User: James Iley
Date Deposited: 04 Jul 2006
Last Modified: 02 Dec 2010 19:50
URI: http://oro.open.ac.uk/id/eprint/3994
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