Utilize este identificador para referenciar este registo:
https://hdl.handle.net/10216/82076
Autor(es): | Gomes, P Araujo, MJ Rodrigues, M Vale, N Azevedo, Z Iley, J Chambel, P Morais, J Moreira, R |
Título: | Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine: scope and limitations |
Data de publicação: | 2004 |
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. |
Assunto: | Química Chemical sciences |
Áreas do conhecimento: | Ciências exactas e naturais::Química Natural sciences::Chemical sciences |
URI: | https://hdl.handle.net/10216/82076 |
Tipo de Documento: | Artigo em Revista Científica Internacional |
Condições de Acesso: | openAccess |
Licença: | https://creativecommons.org/licenses/by-nc/4.0/ |
Aparece nas coleções: | FCUP - Artigo em Revista Científica Internacional |
Este registo está protegido por Licença Creative Commons