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Synthesis, characterization and in vitro anticancer activity of Novel 8,4’ : oxyneolignan analogues

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-ketoeth...

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Main Authors: 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
Format: Artigo
Language: English
Published: Sociedade Brasileira de Química 2018
Subjects:
Compostos orgânicos
Câncer - tratamento
Síntese
Online Access: http://repositorio.unb.br/handle/10482/30697
http://dx.doi.org/10.21577/0103-5053.20170075
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spelling ir-10482-306972019-11-12T12:10:35Z Synthesis, characterization and in vitro anticancer activity of Novel 8,4’ : oxyneolignan analogues 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 Compostos orgânicos Câncer - tratamento Síntese 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. 2018-01-04T19:14:43Z 2018-01-04T19:14:43Z 2017-11 Artigo 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. http://repositorio.unb.br/handle/10482/30697 http://dx.doi.org/10.21577/0103-5053.20170075 en Acesso Aberto Journal 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. application/pdf Sociedade Brasileira de Química
institution REPOSITORIO UNB
collection REPOSITORIO UNB
language English
topic Compostos orgânicos
Câncer - tratamento
Síntese
spellingShingle Compostos orgânicos
Câncer - tratamento
Síntese
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
Synthesis, characterization and in vitro anticancer activity of Novel 8,4’ : oxyneolignan analogues
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.
format Artigo
author 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_sort Souza, Gisele C.
title 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_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_sort synthesis, characterization and in vitro anticancer activity of novel 8,4’ : oxyneolignan analogues
publisher Sociedade Brasileira de Química
publishDate 2018
url http://repositorio.unb.br/handle/10482/30697
http://dx.doi.org/10.21577/0103-5053.20170075
_version_ 1672205438123245568
score 13.657419

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