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Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine
| 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. |
|---|---|
| Autores principais: | Gomes, P |
| Outros Autores: | Araujo, MJ; Rodrigues, M; Vale, N; Azevedo, Z; Iley, J; Chambel, P; Morais, J; Moreira, R |
| Assunto: | Chemistry, Organic |
| Ano: | 2004 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso a metadados |
| Instituição associada: | Universidade de Lisboa |
| Idioma: | inglês |
| Origem: | Repositório da Universidade de Lisboa |
| _version_ | 1866810499411214336 |
|---|---|
| author | Gomes, P |
| author2 | Araujo, MJ Rodrigues, M Vale, N Azevedo, Z Iley, J Chambel, P Morais, J Moreira, R |
| author2_role | author author author author author author author author |
| author_facet | Gomes, P Araujo, MJ Rodrigues, M Vale, N Azevedo, Z Iley, J Chambel, P Morais, J Moreira, R |
| author_role | author |
| contributor_name_str_mv | Repositório Científico de Acesso Aberto da ULisboa |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Gomes, P\"},{\"Person.name\":\"Araujo, MJ\"},{\"Person.name\":\"Rodrigues, M\"},{\"Person.name\":\"Vale, N\"},{\"Person.name\":\"Azevedo, Z\"},{\"Person.name\":\"Iley, J\"},{\"Person.name\":\"Chambel, P\"},{\"Person.name\":\"Morais, J\"},{\"Person.name\":\"Moreira, R\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Repositório Científico de Acesso Aberto da ULisboa |
| datacite.creators.creator.creatorName.fl_str_mv | Gomes, P Araujo, MJ Rodrigues, M Vale, N Azevedo, Z Iley, J Chambel, P Morais, J Moreira, R |
| datacite.date.Accepted.fl_str_mv | 2004-01-01T00:00:00Z |
| datacite.date.available.fl_str_mv | 2015-12-30T10:17:51Z |
| datacite.date.embargoed.fl_str_mv | 2015-12-30T10:17:51Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_14cb |
| datacite.subjects.subject.fl_str_mv | Chemistry, Organic |
| datacite.titles.title.fl_str_mv | Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine scope and limitations |
| dc.contributor.none.fl_str_mv | Repositório Científico de Acesso Aberto da ULisboa |
| dc.creator.none.fl_str_mv | Gomes, P Araujo, MJ Rodrigues, M Vale, N Azevedo, Z Iley, J Chambel, P Morais, J Moreira, R |
| dc.date.Accepted.fl_str_mv | 2004-01-01T00:00:00Z |
| dc.date.available.fl_str_mv | 2015-12-30T10:17:51Z |
| dc.date.embargoed.fl_str_mv | 2015-12-30T10:17:51Z |
| dc.identifier.none.fl_str_mv | http://hdl.handle.net/10451/21278 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | PERGAMON-ELSEVIER SCIENCE LTD |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_14cb |
| dc.subject.none.fl_str_mv | Chemistry, Organic |
| dc.title.fl_str_mv | Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine scope and limitations |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | 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. |
| dirty | 0 |
| eu_rights_str_mv | metadataOnlyAccess |
| format | article |
| id | ul_f1dfd6fffcbe493a54b8a9b0ccc39f80 |
| identifier.url.fl_str_mv | http://hdl.handle.net/10451/21278 |
| instacron_str | ul |
| institution | Universidade de Lisboa |
| instname_str | Universidade de Lisboa |
| language | eng |
| network_acronym_str | ul |
| network_name_str | Repositório da Universidade de Lisboa |
| oai_identifier_str | oai:repositorio.ulisboa.pt:10451/21278 |
| organization_str_mv | urn:organizationAcronym:ul |
| person_str_mv | Gomes, P Araujo, MJ Rodrigues, M Vale, N Azevedo, Z Iley, J Chambel, P Morais, J Moreira, R |
| publishDate | 2004 |
| publisher.none.fl_str_mv | PERGAMON-ELSEVIER SCIENCE LTD |
| reponame_str | Repositório da Universidade de Lisboa |
| repository_id_str | urn:repositoryAcronym:ul |
| service_str_mv | urn:repositoryAcronym:ul |
| spelling | engPERGAMON-ELSEVIER SCIENCE LTDThe 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.Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquinescope and limitationsGomes, PAraujo, MJRodrigues, MVale, NAzevedo, ZIley, JChambel, PMorais, JMoreira, RHostingInstitutionOrganizationalRepositório Científico de Acesso Aberto da ULisboae-mailmailto:repositorio@reitoria.ulisboa.ptrepositorio@reitoria.ulisboa.ptISSNIsPartOf0040-4020DOIIsPartOfhttp://dx.doi.org/10.1016/j.tet.2004.04.0772015-12-30T10:17:51Z20042004-01-01T00:00:00ZHandlehttp://hdl.handle.net/10451/21278http://purl.org/coar/access_right/c_14cbmetadata only accessChemistry, Organicliteraturehttp://purl.org/coar/resource_type/c_6501journal articleTETRAHEDRONVol. 6055515562 |
| spellingShingle | Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine Gomes, P Chemistry, Organic |
| status | SINGLETON |
| subject.fl_str_mv | Chemistry, Organic |
| title | Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine |
| title_full | Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine |
| title_fullStr | Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine |
| title_full_unstemmed | Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine |
| title_short | Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine |
| title_sort | Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine |
| topic | Chemistry, Organic |
| topic_facet | Chemistry, Organic |
| url | http://hdl.handle.net/10451/21278 |
| visible | 1 |