Synthesis and Evaluation of New β-Carboline-3-(4-benzylidene)-4H-oxazol-5-one Derivatives as Antitumor Agents

In the present work, we report the synthesis and in vitro anticancer and antimicrobial activity evaluation of a new series of 1-substituted-β-carboline derivatives bearing a 4-benzylidene-4H-oxazol-5-one unity at C-3. The compound 2-[1-(4-methoxyphenyl)-9H-β-carbolin-3-yl]-4-(benzylidene)-4H-oxazol-...

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Autores principales: Savariz, Franciele Cristina, Foglio, Mary Ann, de Carvalho, João Ernesto, Ruiz, Ana Lúcia T. G., Duarte, Marta C. T., da Rosa, Mauricio Ferreira, Meyer, Emerson, Sarragiotto, Maria Helena
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268609/
https://www.ncbi.nlm.nih.gov/pubmed/22614863
http://dx.doi.org/10.3390/molecules17056100
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author Savariz, Franciele Cristina
Foglio, Mary Ann
de Carvalho, João Ernesto
Ruiz, Ana Lúcia T. G.
Duarte, Marta C. T.
da Rosa, Mauricio Ferreira
Meyer, Emerson
Sarragiotto, Maria Helena
author_facet Savariz, Franciele Cristina
Foglio, Mary Ann
de Carvalho, João Ernesto
Ruiz, Ana Lúcia T. G.
Duarte, Marta C. T.
da Rosa, Mauricio Ferreira
Meyer, Emerson
Sarragiotto, Maria Helena
author_sort Savariz, Franciele Cristina
collection PubMed
description In the present work, we report the synthesis and in vitro anticancer and antimicrobial activity evaluation of a new series of 1-substituted-β-carboline derivatives bearing a 4-benzylidene-4H-oxazol-5-one unity at C-3. The compound 2-[1-(4-methoxyphenyl)-9H-β-carbolin-3-yl]-4-(benzylidene)-4H-oxazol-5-one (11) was the most active derivative, exhibiting a potent cytotoxic activity against glioma (U251), prostate (PC-3) and ovarian (OVCAR-03) cancer cell lines with IC(50) values of 0.48, 1.50 and 1.07 µM, respectively. An in silico study of the ADME properties of the novel synthesized β-carboline derivatives was also performed.
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spelling pubmed-62686092018-12-20 Synthesis and Evaluation of New β-Carboline-3-(4-benzylidene)-4H-oxazol-5-one Derivatives as Antitumor Agents Savariz, Franciele Cristina Foglio, Mary Ann de Carvalho, João Ernesto Ruiz, Ana Lúcia T. G. Duarte, Marta C. T. da Rosa, Mauricio Ferreira Meyer, Emerson Sarragiotto, Maria Helena Molecules Article In the present work, we report the synthesis and in vitro anticancer and antimicrobial activity evaluation of a new series of 1-substituted-β-carboline derivatives bearing a 4-benzylidene-4H-oxazol-5-one unity at C-3. The compound 2-[1-(4-methoxyphenyl)-9H-β-carbolin-3-yl]-4-(benzylidene)-4H-oxazol-5-one (11) was the most active derivative, exhibiting a potent cytotoxic activity against glioma (U251), prostate (PC-3) and ovarian (OVCAR-03) cancer cell lines with IC(50) values of 0.48, 1.50 and 1.07 µM, respectively. An in silico study of the ADME properties of the novel synthesized β-carboline derivatives was also performed. MDPI 2012-05-21 /pmc/articles/PMC6268609/ /pubmed/22614863 http://dx.doi.org/10.3390/molecules17056100 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Savariz, Franciele Cristina
Foglio, Mary Ann
de Carvalho, João Ernesto
Ruiz, Ana Lúcia T. G.
Duarte, Marta C. T.
da Rosa, Mauricio Ferreira
Meyer, Emerson
Sarragiotto, Maria Helena
Synthesis and Evaluation of New β-Carboline-3-(4-benzylidene)-4H-oxazol-5-one Derivatives as Antitumor Agents
title Synthesis and Evaluation of New β-Carboline-3-(4-benzylidene)-4H-oxazol-5-one Derivatives as Antitumor Agents
title_full Synthesis and Evaluation of New β-Carboline-3-(4-benzylidene)-4H-oxazol-5-one Derivatives as Antitumor Agents
title_fullStr Synthesis and Evaluation of New β-Carboline-3-(4-benzylidene)-4H-oxazol-5-one Derivatives as Antitumor Agents
title_full_unstemmed Synthesis and Evaluation of New β-Carboline-3-(4-benzylidene)-4H-oxazol-5-one Derivatives as Antitumor Agents
title_short Synthesis and Evaluation of New β-Carboline-3-(4-benzylidene)-4H-oxazol-5-one Derivatives as Antitumor Agents
title_sort synthesis and evaluation of new β-carboline-3-(4-benzylidene)-4h-oxazol-5-one derivatives as antitumor agents
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268609/
https://www.ncbi.nlm.nih.gov/pubmed/22614863
http://dx.doi.org/10.3390/molecules17056100
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