Publication
Steroselective synthesis of imidazolidin-4-ones from α-amino amides of the antimalarial primaquine and substituted benzaldehydes
| dc.contributor.author | Ferraz, Ricardo | |
| dc.contributor.author | Gomes, José R. B. | |
| dc.contributor.author | Passo, Joana | |
| dc.contributor.author | Oliveira, Eliandre | |
| dc.contributor.author | Moreira, Rui | |
| dc.contributor.author | Gomes, Paula | |
| dc.date.accessioned | 2013-09-24T15:36:19Z | |
| dc.date.available | 2013-09-24T15:36:19Z | |
| dc.date.issued | 2006 | |
| dc.description.abstract | Imidazolidin-4-ones are commonly employed as skeletal modifications in bioactive oligopeptides, either as proline surrogates or for protection of the N-terminal amino acid against aminopeptidase-catalysed hydrolysis . We have been working on the synthesis of imidazolidin-4-ones of the antimalarial primaquine , through acylation of primaquine with an α-amino acid and subsequent reaction of the resulting α-aminoamide with a ketone or aldehyde. Thus, when using racemic primaquine, an optically pure chiral α-amino acid and an aldehyde as starting materials, four imidazolidin-4-one diastereomers are to be expected (Scheme 1). However, we have recently observed that imidazolidin-4-one synthesis was stereoselective when 2-carboxybenzaldehyde (2CBA)* was used, as only two diastereomers were produced2. Computational studies have shown that the imine formed prior to ring closure had, for structures derived from 2CBA, a quasi-cyclic rigid structure2. This rigid conformation is stabilized by an intramolecular hydrogen bond involving the C=O oxygen atom of the 2-carboxyl substituent in 2CBA and the N-H group of the α-amino amide moiety2. These findings led us to postulate that the 2-carbonyl substituent in the benzaldehyde moiety was the key for the stereoselective synthesis of the imidazolidin-4-ones2. | por |
| dc.identifier.uri | http://hdl.handle.net/10400.22/2007 | |
| dc.language.iso | eng | por |
| dc.peerreviewed | yes | por |
| dc.publisher | Instituto Politécnico do Porto. Escola Superior de Tecnologia da Saúde do Porto | por |
| dc.publisher | Universidade do Porto. Faculdade de Ciências da Universidade do Porto | |
| dc.publisher | Universidade do Porto. Faculdade de Farmácia da Universidade do Porto | |
| dc.publisher | Barcelona Science Park | |
| dc.title | Steroselective synthesis of imidazolidin-4-ones from α-amino amides of the antimalarial primaquine and substituted benzaldehydes | por |
| dc.type | conference object | |
| dspace.entity.type | Publication | |
| oaire.citation.conferencePlace | Santiago de Compostela, Espanha | por |
| oaire.citation.title | 4th Spanish-Portuguese-Japanese Organic Chemistry Symposium | por |
| person.familyName | Ferraz | |
| person.givenName | Ricardo | |
| person.identifier.ciencia-id | 001E-71CE-F92D | |
| person.identifier.orcid | 0000-0002-1761-117X | |
| person.identifier.rid | G-5639-2011 | |
| person.identifier.scopus-author-id | 24464208500 | |
| rcaap.rights | openAccess | por |
| rcaap.type | conferenceObject | por |
| relation.isAuthorOfPublication | a5a8faa7-12a5-4b1c-bced-44c895677397 | |
| relation.isAuthorOfPublication.latestForDiscovery | a5a8faa7-12a5-4b1c-bced-44c895677397 |