Synthesis and antiproliferative activity of C-3 functionalized Isobenzofuran-1(3H)-ones

Detalhes bibliográficos
Autor(a) principal: Teixeira, Róbson Ricardo
Data de Publicação: 2013
Outros Autores: Bressan, Gustavo Costa, Pereira, Wagner Luiz, Ferreira, Joana Gasperazzo, Oliveira, Fabrício Marques de, Thomaz, Deborah Campos
Tipo de documento: Artigo
Idioma: eng
Título da fonte: LOCUS Repositório Institucional da UFV
Texto Completo: https://doi.org/10.3390/molecules18021881
http://www.locus.ufv.br/handle/123456789/12810
Resumo: A series of thirteen C-3 functionalized isobenzofuran-1(3H)-ones (phtalides) was synthesized via condensation, aromatization, and acetylation reactions. NMR (one and two dimensional experiments), IR, and mass spectrometry analysis allowed confirmation of the identity of the synthesized compounds. The substances were submitted to in vitro bioassays against U937 (lymphoma) and K562 (myeloid leukemia) cancer cell lines using the MTT cytotoxicity assay. Some derivatives inhibited 90% of cell viability at 100 µM. Also, two phtalides presented biological activity superior than that of etoposide (VP16), a commercial drug used as a positive control in the assays. In silico drug properties of the evaluated compounds were calculated and the results are discussed.
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spelling Teixeira, Róbson RicardoBressan, Gustavo CostaPereira, Wagner LuizFerreira, Joana GasperazzoOliveira, Fabrício Marques deThomaz, Deborah Campos2017-11-07T11:09:50Z2017-11-07T11:09:50Z2013-02-0114203049https://doi.org/10.3390/molecules18021881http://www.locus.ufv.br/handle/123456789/12810A series of thirteen C-3 functionalized isobenzofuran-1(3H)-ones (phtalides) was synthesized via condensation, aromatization, and acetylation reactions. NMR (one and two dimensional experiments), IR, and mass spectrometry analysis allowed confirmation of the identity of the synthesized compounds. The substances were submitted to in vitro bioassays against U937 (lymphoma) and K562 (myeloid leukemia) cancer cell lines using the MTT cytotoxicity assay. Some derivatives inhibited 90% of cell viability at 100 µM. Also, two phtalides presented biological activity superior than that of etoposide (VP16), a commercial drug used as a positive control in the assays. In silico drug properties of the evaluated compounds were calculated and the results are discussed.engMolecules18(2), p. 1881-1896, February 2013PhtalidesAntiproliferative activityIsobenzofuran-1(3H)-oneSynthesis and antiproliferative activity of C-3 functionalized Isobenzofuran-1(3H)-onesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfinfo:eu-repo/semantics/openAccessreponame:LOCUS Repositório Institucional da UFVinstname:Universidade Federal de Viçosa (UFV)instacron:UFVORIGINALmolecules-18-01881.pdfmolecules-18-01881.pdfTexto completoapplication/pdf275945https://locus.ufv.br//bitstream/123456789/12810/1/molecules-18-01881.pdf8e57ec5f50e3dff11ca725f94d04ac49MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://locus.ufv.br//bitstream/123456789/12810/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52THUMBNAILmolecules-18-01881.pdf.jpgmolecules-18-01881.pdf.jpgIM Thumbnailimage/jpeg5060https://locus.ufv.br//bitstream/123456789/12810/3/molecules-18-01881.pdf.jpga43fa8eb1c6a2000e1bae5251a6178d4MD53123456789/128102017-11-07 22:00:36.663oai:locus.ufv.br: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Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452017-11-08T01:00:36LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false
dc.title.en.fl_str_mv Synthesis and antiproliferative activity of C-3 functionalized Isobenzofuran-1(3H)-ones
title Synthesis and antiproliferative activity of C-3 functionalized Isobenzofuran-1(3H)-ones
spellingShingle Synthesis and antiproliferative activity of C-3 functionalized Isobenzofuran-1(3H)-ones
Teixeira, Róbson Ricardo
Phtalides
Antiproliferative activity
Isobenzofuran-1(3H)-one
title_short Synthesis and antiproliferative activity of C-3 functionalized Isobenzofuran-1(3H)-ones
title_full Synthesis and antiproliferative activity of C-3 functionalized Isobenzofuran-1(3H)-ones
title_fullStr Synthesis and antiproliferative activity of C-3 functionalized Isobenzofuran-1(3H)-ones
title_full_unstemmed Synthesis and antiproliferative activity of C-3 functionalized Isobenzofuran-1(3H)-ones
title_sort Synthesis and antiproliferative activity of C-3 functionalized Isobenzofuran-1(3H)-ones
author Teixeira, Róbson Ricardo
author_facet Teixeira, Róbson Ricardo
Bressan, Gustavo Costa
Pereira, Wagner Luiz
Ferreira, Joana Gasperazzo
Oliveira, Fabrício Marques de
Thomaz, Deborah Campos
author_role author
author2 Bressan, Gustavo Costa
Pereira, Wagner Luiz
Ferreira, Joana Gasperazzo
Oliveira, Fabrício Marques de
Thomaz, Deborah Campos
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Teixeira, Róbson Ricardo
Bressan, Gustavo Costa
Pereira, Wagner Luiz
Ferreira, Joana Gasperazzo
Oliveira, Fabrício Marques de
Thomaz, Deborah Campos
dc.subject.pt-BR.fl_str_mv Phtalides
Antiproliferative activity
Isobenzofuran-1(3H)-one
topic Phtalides
Antiproliferative activity
Isobenzofuran-1(3H)-one
description A series of thirteen C-3 functionalized isobenzofuran-1(3H)-ones (phtalides) was synthesized via condensation, aromatization, and acetylation reactions. NMR (one and two dimensional experiments), IR, and mass spectrometry analysis allowed confirmation of the identity of the synthesized compounds. The substances were submitted to in vitro bioassays against U937 (lymphoma) and K562 (myeloid leukemia) cancer cell lines using the MTT cytotoxicity assay. Some derivatives inhibited 90% of cell viability at 100 µM. Also, two phtalides presented biological activity superior than that of etoposide (VP16), a commercial drug used as a positive control in the assays. In silico drug properties of the evaluated compounds were calculated and the results are discussed.
publishDate 2013
dc.date.issued.fl_str_mv 2013-02-01
dc.date.accessioned.fl_str_mv 2017-11-07T11:09:50Z
dc.date.available.fl_str_mv 2017-11-07T11:09:50Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv https://doi.org/10.3390/molecules18021881
http://www.locus.ufv.br/handle/123456789/12810
dc.identifier.issn.none.fl_str_mv 14203049
identifier_str_mv 14203049
url https://doi.org/10.3390/molecules18021881
http://www.locus.ufv.br/handle/123456789/12810
dc.language.iso.fl_str_mv eng
language eng
dc.relation.ispartofseries.pt-BR.fl_str_mv 18(2), p. 1881-1896, February 2013
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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dc.publisher.none.fl_str_mv Molecules
publisher.none.fl_str_mv Molecules
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reponame_str LOCUS Repositório Institucional da UFV
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