Publicação
Synthesis and trypanocidal activity of 7, 2'-dioxygenated isoflavones and oxypropanolamine derivatives
| Resumo: | 7, 2'-Dihydroxyisoflavone was shown to be active against the bloodstream trypomastigote form of Trypanosoma cruzi, the etiologic agent of Chagas' disease. Amphiphilic derivatives of this isoflavone were synthezised aiming to obtain hydrosoluble compounds of potential use as prophylactic agents to be added to blood for transfusion. This isoflavone was obtained by demethylation of 7-hydroxy-2'-methoxyisoflavone that was synthesized via the intermediate deoxybenzoin. Its reaction with epichlorohydrin, followed by aminolysis with diethylamine, afforded the 7-oxypropanolamine which on treatment with methyl iodide gave the corresponding ammonium salt. The 7-hydroxy-2'-methoxyisoflavone was inactive in the in vitro assays, the 7-oxypropanolamine was more active than 7, 2'-dihydroxyisoflavone while the ammonium salt has not eliminated the parasite from the blood besides causing total lysis of the erythrocytes. The simple synthetic procedures described in the present paper can be used to provide gram quantities of 7, 2'-dihydroxyisoflavone and its 7-oxypropanolamine derivative that should be further investigated in in vivo murine models as potential chemotherapeutic agents for treatment of Chagas' disease. |
|---|---|
| Autores principais: | Faria,Terezinha de J. |
| Outros Autores: | Silva,Luiz G. Fonseca e; Souza Filho,José D. de; Chiari,Egler; Oliveira,Alaíde B. de |
| Assunto: | isoflavones aryloxypropanolamines trypanocidal activity Trypanosoma cruzi |
| Ano: | 2005 |
| País: | Brasil |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | IBICT |
| Idioma: | inglês |
| Origem: | Oasisbr |
| _version_ | 1871506537079373824 |
|---|---|
| author | Faria,Terezinha de J. |
| author2 | Silva,Luiz G. Fonseca e Souza Filho,José D. de Chiari,Egler Oliveira,Alaíde B. de |
| author2_role | author author author author |
| author_facet | Faria,Terezinha de J. Silva,Luiz G. Fonseca e Souza Filho,José D. de Chiari,Egler Oliveira,Alaíde B. de |
| author_role | author |
| country_str | BR |
| creators_json_txt | [{\"Person.name\":\"Faria,Terezinha de J.\"},{\"Person.name\":\"Silva,Luiz G. Fonseca e\"},{\"Person.name\":\"Souza Filho,José D. de\"},{\"Person.name\":\"Chiari,Egler\"},{\"Person.name\":\"Oliveira,Alaíde B. de\"}] |
| datacite.creators.creator.creatorName.fl_str_mv | Faria,Terezinha de J. Silva,Luiz G. Fonseca e Souza Filho,José D. de Chiari,Egler Oliveira,Alaíde B. de |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | isoflavones aryloxypropanolamines trypanocidal activity Trypanosoma cruzi |
| datacite.titles.title.fl_str_mv | Synthesis and trypanocidal activity of 7, 2'-dioxygenated isoflavones and oxypropanolamine derivatives |
| dc.creator.none.fl_str_mv | Faria,Terezinha de J. Silva,Luiz G. Fonseca e Souza Filho,José D. de Chiari,Egler Oliveira,Alaíde B. de |
| dc.format.none.fl_str_mv | text/html |
| dc.identifier.none.fl_str_mv | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000800020 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Sociedade Brasileira de Química |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.source.none.fl_str_mv | Journal of the Brazilian Chemical Society v.16 n.6b 2005 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
| dc.subject.none.fl_str_mv | isoflavones aryloxypropanolamines trypanocidal activity Trypanosoma cruzi |
| dc.title.fl_str_mv | Synthesis and trypanocidal activity of 7, 2'-dioxygenated isoflavones and oxypropanolamine derivatives |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | 7, 2'-Dihydroxyisoflavone was shown to be active against the bloodstream trypomastigote form of Trypanosoma cruzi, the etiologic agent of Chagas' disease. Amphiphilic derivatives of this isoflavone were synthezised aiming to obtain hydrosoluble compounds of potential use as prophylactic agents to be added to blood for transfusion. This isoflavone was obtained by demethylation of 7-hydroxy-2'-methoxyisoflavone that was synthesized via the intermediate deoxybenzoin. Its reaction with epichlorohydrin, followed by aminolysis with diethylamine, afforded the 7-oxypropanolamine which on treatment with methyl iodide gave the corresponding ammonium salt. The 7-hydroxy-2'-methoxyisoflavone was inactive in the in vitro assays, the 7-oxypropanolamine was more active than 7, 2'-dihydroxyisoflavone while the ammonium salt has not eliminated the parasite from the blood besides causing total lysis of the erythrocytes. The simple synthetic procedures described in the present paper can be used to provide gram quantities of 7, 2'-dihydroxyisoflavone and its 7-oxypropanolamine derivative that should be further investigated in in vivo murine models as potential chemotherapeutic agents for treatment of Chagas' disease. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| id | oasisbr_3fd53208d401cec8a56c3a0286dcd2c1 |
| identifier.url.fl_str_mv | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000800020 |
| inst_facet_str | urn:organizationAcronym:oasisbr{{{_:::_}}}IBICT |
| instacron_str | OASISBR |
| institution | IBICT |
| instname_str | IBICT |
| language | eng |
| network_acronym_str | oasisbr |
| network_name_str | Oasisbr |
| oai_identifier_str | oai:scielo:S0103-50532005000800020 |
| organization_str_mv | urn:organizationAcronym:oasisbr |
| person_str_mv | Faria,Terezinha de J. Silva,Luiz G. Fonseca e Souza Filho,José D. de Chiari,Egler Oliveira,Alaíde B. de |
| publishDate | 2005 |
| publisher.none.fl_str_mv | Sociedade Brasileira de Química |
| repo_facet_str | urn:repositoryAcronym:oasisbr{{{_:::_}}}Oasisbr |
| reponame_str | Oasisbr |
| repository_id_str | urn:repositoryAcronym:oasisbr |
| service_str_mv | urn:repositoryAcronym:oasisbr |
| spelling | Synthesis and trypanocidal activity of 7, 2'-dioxygenated isoflavones and oxypropanolamine derivativesFaria,Terezinha de J.Silva,Luiz G. Fonseca eSouza Filho,José D. deChiari,EglerOliveira,Alaíde B. deisoflavonesaryloxypropanolaminestrypanocidal activityTrypanosoma cruziopen accesshttp://purl.org/coar/access_right/c_abf2http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000800020URLhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000800020URLHasVersion2005-11-017, 2'-Dihydroxyisoflavone was shown to be active against the bloodstream trypomastigote form of Trypanosoma cruzi, the etiologic agent of Chagas' disease. Amphiphilic derivatives of this isoflavone were synthezised aiming to obtain hydrosoluble compounds of potential use as prophylactic agents to be added to blood for transfusion. This isoflavone was obtained by demethylation of 7-hydroxy-2'-methoxyisoflavone that was synthesized via the intermediate deoxybenzoin. Its reaction with epichlorohydrin, followed by aminolysis with diethylamine, afforded the 7-oxypropanolamine which on treatment with methyl iodide gave the corresponding ammonium salt. The 7-hydroxy-2'-methoxyisoflavone was inactive in the in vitro assays, the 7-oxypropanolamine was more active than 7, 2'-dihydroxyisoflavone while the ammonium salt has not eliminated the parasite from the blood besides causing total lysis of the erythrocytes. The simple synthetic procedures described in the present paper can be used to provide gram quantities of 7, 2'-dihydroxyisoflavone and its 7-oxypropanolamine derivative that should be further investigated in in vivo murine models as potential chemotherapeutic agents for treatment of Chagas' disease.engtext/htmlSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.16 n.6b 2005reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQjournal articlehttp://purl.org/coar/resource_type/c_6501literatureVoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85 |
| spellingShingle | Synthesis and trypanocidal activity of 7, 2'-dioxygenated isoflavones and oxypropanolamine derivatives Faria,Terezinha de J. isoflavones aryloxypropanolamines trypanocidal activity Trypanosoma cruzi |
| status | SINGLETON |
| status_str | VoR |
| subject.fl_str_mv | isoflavones aryloxypropanolamines trypanocidal activity Trypanosoma cruzi |
| title | Synthesis and trypanocidal activity of 7, 2'-dioxygenated isoflavones and oxypropanolamine derivatives |
| title_full | Synthesis and trypanocidal activity of 7, 2'-dioxygenated isoflavones and oxypropanolamine derivatives |
| title_fullStr | Synthesis and trypanocidal activity of 7, 2'-dioxygenated isoflavones and oxypropanolamine derivatives |
| title_full_unstemmed | Synthesis and trypanocidal activity of 7, 2'-dioxygenated isoflavones and oxypropanolamine derivatives |
| title_short | Synthesis and trypanocidal activity of 7, 2'-dioxygenated isoflavones and oxypropanolamine derivatives |
| title_sort | Synthesis and trypanocidal activity of 7, 2'-dioxygenated isoflavones and oxypropanolamine derivatives |
| topic | isoflavones aryloxypropanolamines trypanocidal activity Trypanosoma cruzi |
| topic_facet | isoflavones aryloxypropanolamines trypanocidal activity Trypanosoma cruzi |
| url | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000800020 |
| visible | 1 |
Atividades financiadas
Não foram encontrados projetos financiados.