Publicação
Synthesis and in vitro Antiproliferative Activity of Flavone and 6-Hydroxyflavone Oxime Ethers Derivatives
| Resumo: | Herein we report the synthesis of a series of O-alkyl oximes of flavone and 6-hydroxyflavone using a simple experimental protocol under solvent free conditions with yields up to 87%. Cytotoxicity of all compounds was evaluated against MDA-MB-231, PC-3, A-549 and MRC-5 cells. IC50 values for two compounds were determined to be in the range 28.7-47.8 µM against all tested cell lines. Oxime ethers derivatives showed IC50 values between 28.7 and 49.5 µM against MDA-MB-231, while the best activity was obtained for 6-hydroxyflavone with an IC50 of 3.4 µM against this cell line. Compounds containing the substituent hydroxyl at the position six of flavone system displayed the best antiproliferative activity over MDA-MB-231 cells, being necessary this group to improve the sensibility on this type of cells. The antiproliferative activity of 6-hydroxyflavone is drastically diminished when the carbonyl group of flavone is changed by an oxime ether. |
|---|---|
| Autores principais: | Díaz,John E. |
| Outros Autores: | Martinez,Diana C.; López,Lina V.; Mendez,Gina M.; Vera,Ricardo; Loaiza,Alix E. |
| Assunto: | synthesis oxime ethers flavone 6-hydroxyflavone antiproliferative activity |
| Ano: | 2018 |
| País: | Brasil |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | IBICT |
| Idioma: | inglês |
| Origem: | Oasisbr |
| _version_ | 1871506692097703936 |
|---|---|
| author | Díaz,John E. |
| author2 | Martinez,Diana C. López,Lina V. Mendez,Gina M. Vera,Ricardo Loaiza,Alix E. |
| author2_role | author author author author author |
| author_facet | Díaz,John E. Martinez,Diana C. López,Lina V. Mendez,Gina M. Vera,Ricardo Loaiza,Alix E. |
| author_role | author |
| country_str | BR |
| creators_json_txt | [{\"Person.name\":\"Díaz,John E.\"},{\"Person.name\":\"Martinez,Diana C.\"},{\"Person.name\":\"López,Lina V.\"},{\"Person.name\":\"Mendez,Gina M.\"},{\"Person.name\":\"Vera,Ricardo\"},{\"Person.name\":\"Loaiza,Alix E.\"}] |
| datacite.creators.creator.creatorName.fl_str_mv | Díaz,John E. Martinez,Diana C. López,Lina V. Mendez,Gina M. Vera,Ricardo Loaiza,Alix E. |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | synthesis oxime ethers flavone 6-hydroxyflavone antiproliferative activity |
| datacite.titles.title.fl_str_mv | Synthesis and in vitro Antiproliferative Activity of Flavone and 6-Hydroxyflavone Oxime Ethers Derivatives |
| dc.creator.none.fl_str_mv | Díaz,John E. Martinez,Diana C. López,Lina V. Mendez,Gina M. Vera,Ricardo Loaiza,Alix E. |
| dc.format.none.fl_str_mv | text/html |
| dc.identifier.none.fl_str_mv | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000100177 |
| 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.29 n.1 2018 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
| dc.subject.none.fl_str_mv | synthesis oxime ethers flavone 6-hydroxyflavone antiproliferative activity |
| dc.title.fl_str_mv | Synthesis and in vitro Antiproliferative Activity of Flavone and 6-Hydroxyflavone Oxime Ethers Derivatives |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | Herein we report the synthesis of a series of O-alkyl oximes of flavone and 6-hydroxyflavone using a simple experimental protocol under solvent free conditions with yields up to 87%. Cytotoxicity of all compounds was evaluated against MDA-MB-231, PC-3, A-549 and MRC-5 cells. IC50 values for two compounds were determined to be in the range 28.7-47.8 µM against all tested cell lines. Oxime ethers derivatives showed IC50 values between 28.7 and 49.5 µM against MDA-MB-231, while the best activity was obtained for 6-hydroxyflavone with an IC50 of 3.4 µM against this cell line. Compounds containing the substituent hydroxyl at the position six of flavone system displayed the best antiproliferative activity over MDA-MB-231 cells, being necessary this group to improve the sensibility on this type of cells. The antiproliferative activity of 6-hydroxyflavone is drastically diminished when the carbonyl group of flavone is changed by an oxime ether. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| id | oasisbr_4657693c78119d654d2fee8bca3c3dc6 |
| identifier.url.fl_str_mv | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000100177 |
| 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:S0103-50532018000100177 |
| organization_str_mv | urn:organizationAcronym:oasisbr |
| person_str_mv | Díaz,John E. Martinez,Diana C. López,Lina V. Mendez,Gina M. Vera,Ricardo Loaiza,Alix E. |
| publishDate | 2018 |
| publisher.none.fl_str_mv | Sociedade Brasileira de Química |
| repo_facet_str | urn:repositoryAcronym:oasisbr{{{_:::_}}}Oasisbr |
| reponame_str | Oasisbr |
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| service_str_mv | urn:repositoryAcronym:oasisbr |
| spelling | Synthesis and in vitro Antiproliferative Activity of Flavone and 6-Hydroxyflavone Oxime Ethers DerivativesDíaz,John E.Martinez,Diana C.López,Lina V.Mendez,Gina M.Vera,RicardoLoaiza,Alix E.synthesisoxime ethersflavone6-hydroxyflavoneantiproliferative activityopen accesshttp://purl.org/coar/access_right/c_abf2http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000100177URLhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000100177URLHasVersion2018-01-01Herein we report the synthesis of a series of O-alkyl oximes of flavone and 6-hydroxyflavone using a simple experimental protocol under solvent free conditions with yields up to 87%. Cytotoxicity of all compounds was evaluated against MDA-MB-231, PC-3, A-549 and MRC-5 cells. IC50 values for two compounds were determined to be in the range 28.7-47.8 µM against all tested cell lines. Oxime ethers derivatives showed IC50 values between 28.7 and 49.5 µM against MDA-MB-231, while the best activity was obtained for 6-hydroxyflavone with an IC50 of 3.4 µM against this cell line. Compounds containing the substituent hydroxyl at the position six of flavone system displayed the best antiproliferative activity over MDA-MB-231 cells, being necessary this group to improve the sensibility on this type of cells. The antiproliferative activity of 6-hydroxyflavone is drastically diminished when the carbonyl group of flavone is changed by an oxime ether.engtext/htmlSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.29 n.1 2018reponame: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 in vitro Antiproliferative Activity of Flavone and 6-Hydroxyflavone Oxime Ethers Derivatives Díaz,John E. synthesis oxime ethers flavone 6-hydroxyflavone antiproliferative activity |
| status | SINGLETON |
| status_str | VoR |
| subject.fl_str_mv | synthesis oxime ethers flavone 6-hydroxyflavone antiproliferative activity |
| title | Synthesis and in vitro Antiproliferative Activity of Flavone and 6-Hydroxyflavone Oxime Ethers Derivatives |
| title_full | Synthesis and in vitro Antiproliferative Activity of Flavone and 6-Hydroxyflavone Oxime Ethers Derivatives |
| title_fullStr | Synthesis and in vitro Antiproliferative Activity of Flavone and 6-Hydroxyflavone Oxime Ethers Derivatives |
| title_full_unstemmed | Synthesis and in vitro Antiproliferative Activity of Flavone and 6-Hydroxyflavone Oxime Ethers Derivatives |
| title_short | Synthesis and in vitro Antiproliferative Activity of Flavone and 6-Hydroxyflavone Oxime Ethers Derivatives |
| title_sort | Synthesis and in vitro Antiproliferative Activity of Flavone and 6-Hydroxyflavone Oxime Ethers Derivatives |
| topic | synthesis oxime ethers flavone 6-hydroxyflavone antiproliferative activity |
| topic_facet | synthesis oxime ethers flavone 6-hydroxyflavone antiproliferative activity |
| url | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000100177 |
| visible | 1 |
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