Synthesis, characterization and in vitro anticancer activity of Novel 8,4’ : oxyneolignan analogues
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| Autor principal: | |
|---|---|
| Data de Publicação: | 2017 |
| Outros Autores: | , , , , , |
| Formato: | Artigo |
| Idioma: | eng |
| Fonte: | Repositório Institucional da UnB |
| Texto Completo: | http://repositorio.unb.br/handle/10482/30697 http://dx.doi.org/10.21577/0103-5053.20170075 |
Resumo: | Neolignans are a class of natural products with a wide range of biological effects. These substances are of great synthetic and biological interest, especially in searching for novel anticancer agents. In this paper, we report the synthesis of a new subclass of 8,4’-oxyneolignan analogues (β-ketoethers and β-ketoesters) and their cell viability assay on twenty four different cancer cells, among leukemias and carcinomas. Three compounds inhibited the growth of most human cancer cells. 2-Oxo-2-phenylethyl(2E)-3-[4-(2-oxo-2-phenylethoxy) phenyl]prop-2-enoate showed an antiproliferative activity superior to doxorubicin for U-87, U-138 MG and H1299 cell types and (E)-2-oxo-2-phenylethyl 3-(3-methoxy-4-(2-oxo-2-phenylethoxy)phenyl)acrylate was found to be very selective, demonstrating a growth inhibition of 92.0% against KG-1 cells. Furthermore, 1-oxo-1-phenylpropan-2-yl cinnamate exhibited significant inhibition activity in a range of 52.2 to 91.2% against twelve kinds of leukemia cell lines, revealing excellent results and very comparable to the reference drug. |
| _version_ | 1871442374876463104 |
|---|---|
| author | Souza, Gisele C. |
| author2 | Franchi Jr., Gilberto C. Nowill, Alexandre E. Santos, Lourivaldo S. Alves, Cláudio N. Barata, Lauro E. S. Andrade, Carlos Kleber Zago de |
| author2_role | author author author author author author |
| author_browse | Alves, Cláudio N. Andrade, Carlos Kleber Zago de Barata, Lauro E. S. Franchi Jr., Gilberto C. Nowill, Alexandre E. Santos, Lourivaldo S. Souza, Gisele C. |
| author_facet | Souza, Gisele C. Franchi Jr., Gilberto C. Nowill, Alexandre E. Santos, Lourivaldo S. Alves, Cláudio N. Barata, Lauro E. S. Andrade, Carlos Kleber Zago de |
| author_role | author |
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| bitstream.url.fl_str_mv | http://repositorio2.unb.br/jspui/bitstream/10482/30697/1/ARTIGO_SynthesisCharacterizationVitro.pdf |
| collection | Repositório Institucional da UnB |
| dc.contributor.author.fl_str_mv | Souza, Gisele C. Franchi Jr., Gilberto C. Nowill, Alexandre E. Santos, Lourivaldo S. Alves, Cláudio N. Barata, Lauro E. S. Andrade, Carlos Kleber Zago de |
| dc.date.accessioned.fl_str_mv | 2018-01-04T19:14:43Z |
| dc.date.available.fl_str_mv | 2018-01-04T19:14:43Z |
| dc.date.issued.fl_str_mv | 2017-11 |
| dc.identifier.citation.fl_str_mv | SOUZA, Gisele C. et al. Synthesis, characterization and in vitro anticancer activity of Novel 8,4’-Oxyneolignan Analogues. Journal of the Brazilian Chemical Society, São Paulo, v. 28, n. 11, p. 2229-2243, nov. 2017. Disponível em: <http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017001102229&lng=en&nrm=iso>. Acesso em: 1 fev. 2018. doi: http://dx.doi.org/10.21577/0103-5053.20170075. |
| dc.identifier.doi.pt_BR.fl_str_mv | http://dx.doi.org/10.21577/0103-5053.20170075 |
| dc.identifier.uri.fl_str_mv | http://repositorio.unb.br/handle/10482/30697 |
| dc.language.iso.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Sociedade Brasileira de Química |
| dc.rights.driver.fl_str_mv | info:eu-repo/semantics/openAccess |
| dc.source.none.fl_str_mv | reponame:Repositório Institucional da UnB instname:Universidade de Brasília (UnB) instacron:UNB |
| dc.subject.keyword.pt_BR.fl_str_mv | Compostos orgânicos Câncer - tratamento Síntese |
| dc.title.pt_BR.fl_str_mv | Synthesis, characterization and in vitro anticancer activity of Novel 8,4’ : oxyneolignan analogues |
| dc.type.driver.fl_str_mv | info:eu-repo/semantics/article |
| dc.type.status.fl_str_mv | info:eu-repo/semantics/publishedVersion |
| description | Neolignans are a class of natural products with a wide range of biological effects. These substances are of great synthetic and biological interest, especially in searching for novel anticancer agents. In this paper, we report the synthesis of a new subclass of 8,4’-oxyneolignan analogues (β-ketoethers and β-ketoesters) and their cell viability assay on twenty four different cancer cells, among leukemias and carcinomas. Three compounds inhibited the growth of most human cancer cells. 2-Oxo-2-phenylethyl(2E)-3-[4-(2-oxo-2-phenylethoxy) phenyl]prop-2-enoate showed an antiproliferative activity superior to doxorubicin for U-87, U-138 MG and H1299 cell types and (E)-2-oxo-2-phenylethyl 3-(3-methoxy-4-(2-oxo-2-phenylethoxy)phenyl)acrylate was found to be very selective, demonstrating a growth inhibition of 92.0% against KG-1 cells. Furthermore, 1-oxo-1-phenylpropan-2-yl cinnamate exhibited significant inhibition activity in a range of 52.2 to 91.2% against twelve kinds of leukemia cell lines, revealing excellent results and very comparable to the reference drug. |
| eu_rights_str_mv | openAccess |
| format | article |
| id | UNB_7b7d5653a44cb89d26bc82e2deed3a2a |
| identifier_str_mv | SOUZA, Gisele C. et al. Synthesis, characterization and in vitro anticancer activity of Novel 8,4’-Oxyneolignan Analogues. Journal of the Brazilian Chemical Society, São Paulo, v. 28, n. 11, p. 2229-2243, nov. 2017. Disponível em: <http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017001102229&lng=en&nrm=iso>. Acesso em: 1 fev. 2018. doi: http://dx.doi.org/10.21577/0103-5053.20170075. |
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| language | eng |
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| oai_identifier_str | oai:repositorio.unb.br:10482/30697 |
| publishDate | 2017 |
| publishDateSort | 2017 |
| publisher.none.fl_str_mv | Sociedade Brasileira de Química |
| reponame_str | Repositório Institucional da UnB |
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| spelling | Souza, Gisele C.Franchi Jr., Gilberto C.Nowill, Alexandre E.Santos, Lourivaldo S.Alves, Cláudio N.Barata, Lauro E. S.Andrade, Carlos Kleber Zago de2018-01-04T19:14:43Z2018-01-04T19:14:43Z2017-11SOUZA, Gisele C. et al. Synthesis, characterization and in vitro anticancer activity of Novel 8,4’-Oxyneolignan Analogues. Journal of the Brazilian Chemical Society, São Paulo, v. 28, n. 11, p. 2229-2243, nov. 2017. Disponível em: <http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017001102229&lng=en&nrm=iso>. Acesso em: 1 fev. 2018. doi: http://dx.doi.org/10.21577/0103-5053.20170075.http://repositorio.unb.br/handle/10482/30697http://dx.doi.org/10.21577/0103-5053.20170075Sociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society - This is an Open Access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0). Fonte: http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017001102229&lng=en&nrm=iso. Acesso em: 1 fev. 2017.info:eu-repo/semantics/openAccessSynthesis, characterization and in vitro anticancer activity of Novel 8,4’ : oxyneolignan analoguesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleCompostos orgânicosCâncer - tratamentoSínteseNeolignans are a class of natural products with a wide range of biological effects. These substances are of great synthetic and biological interest, especially in searching for novel anticancer agents. In this paper, we report the synthesis of a new subclass of 8,4’-oxyneolignan analogues (β-ketoethers and β-ketoesters) and their cell viability assay on twenty four different cancer cells, among leukemias and carcinomas. Three compounds inhibited the growth of most human cancer cells. 2-Oxo-2-phenylethyl(2E)-3-[4-(2-oxo-2-phenylethoxy) phenyl]prop-2-enoate showed an antiproliferative activity superior to doxorubicin for U-87, U-138 MG and H1299 cell types and (E)-2-oxo-2-phenylethyl 3-(3-methoxy-4-(2-oxo-2-phenylethoxy)phenyl)acrylate was found to be very selective, demonstrating a growth inhibition of 92.0% against KG-1 cells. Furthermore, 1-oxo-1-phenylpropan-2-yl cinnamate exhibited significant inhibition activity in a range of 52.2 to 91.2% against twelve kinds of leukemia cell lines, revealing excellent results and very comparable to the reference drug.Instituto de Química (IQ)engreponame:Repositório Institucional da UnBinstname:Universidade de Brasília (UnB)instacron:UNBORIGINALARTIGO_SynthesisCharacterizationVitro.pdfARTIGO_SynthesisCharacterizationVitro.pdfapplication/pdf1063769http://repositorio2.unb.br/jspui/bitstream/10482/30697/1/ARTIGO_SynthesisCharacterizationVitro.pdf95faf7c9a2baff7e84379ceb3a207b54MD51open access10482/306972023-10-20 11:01:19.498open accessoai:repositorio.unb.br:10482/30697Repositório InstitucionalPUBhttps://repositorio.unb.br/oai/requestrepositorio@unb.bropendoar:2023-10-20T14:01:19Repositório Institucional da UnB - Universidade de Brasília (UnB) |
| spellingShingle | Synthesis, characterization and in vitro anticancer activity of Novel 8,4’ : oxyneolignan analogues Souza, Gisele C. Compostos orgânicos Câncer - tratamento Síntese |
| status_str | publishedVersion |
| title | Synthesis, characterization and in vitro anticancer activity of Novel 8,4’ : oxyneolignan analogues |
| title_full | Synthesis, characterization and in vitro anticancer activity of Novel 8,4’ : oxyneolignan analogues |
| title_fullStr | Synthesis, characterization and in vitro anticancer activity of Novel 8,4’ : oxyneolignan analogues |
| title_full_unstemmed | Synthesis, characterization and in vitro anticancer activity of Novel 8,4’ : oxyneolignan analogues |
| title_short | Synthesis, characterization and in vitro anticancer activity of Novel 8,4’ : oxyneolignan analogues |
| title_sort | Synthesis, characterization and in vitro anticancer activity of Novel 8,4’ : oxyneolignan analogues |
| topic | Compostos orgânicos Câncer - tratamento Síntese |
| url | http://repositorio.unb.br/handle/10482/30697 http://dx.doi.org/10.21577/0103-5053.20170075 |