Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas
Autor(a) principal: | |
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Data de Publicação: | 2017 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFG |
Texto Completo: | http://repositorio.bc.ufg.br/tede/handle/tede/7922 |
Resumo: | The chalcones are key intermediates for the biosynthesis of flavonoids and have shown an abundance of pharmacological effects including the antitumor effect. Thus, the synthesis and characterization of several chalcones and derivatives become important to develop a new class of compounds having antitumor activity. In the present work, the synthesis of chalcones, nitrochalcone sulfonamides and quinolinones was performed. By adjusting the reaction time and the sequence of the reactions, hybrids of open-chain chalcone sulfonamide whose molecular hybridization occurred at the ortho position of the benzoyl chalcone group through the Claisen- Schmidt condensation of acetophenone sulfonamide and nitrobenzaldehyde can be obtained at shorter reaction times, whereas quinolinone from cyclization at β carbon can be achieved if the reaction is stopped sequentially later. It is also noted that a novel structure, a chalcone (bis) sulfonamide, was prepared when chalcone was first synthesized and then reacted with benzenesulfonyl chloride. From the sulfonamide chalcones prepared with the m- aminoacetophenone sulfonamide and the o-, m- and p-nitrobenzaldehyde, a single product was formed. Among the 21 compounds prepared, five were ketone sulfonamides and sixteen were hybrid compounds (chalcones, chalcones, sulfonamides and quinolinones), which were purified by extraction, recrystallization and column chromatography and characterized by small molecule crystallography, melting point, Proton Nuclear Magnetic Resonance ( 1 H NMR) and infrared IV (IR). The antitumor activity was evaluated against three cancer cell lines: SF-295 (human glioblastoma), PC-3 (prostate) and HCT-116 (colon). Compounds 39, 40, 42, 43, 45a, 48a, 48b, 48c, 49 and 51 were cytotoxic to the three tumor cell lines tested. However, the quinolinones showed no relevant cytotoxic effect. It is also worth noting that compound 45a with a higher cytotoxic effect than doxorubicin, a drug used today against the three cancer cell lines evaluated, was a promising prototype for a new drug. |
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Noda Pérez, Caridadhttp://lattes.cnpq.br/8518548259609686Martins, Felipe Terrahttp://lattes.cnpq.br/0466799995060671Noda Pérez, CaridadMoraes, Manoel Odorico deLee, Chen ChenCamargo, Ademir JoãoVaz, Boniek Gontijohttp://lattes.cnpq.br/3395145363927567Castro, Mirian Rita Carrilho de2017-10-30T10:26:18Z2017-09-01CASTRO, M. R. C. Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas. 2017. 206 f. Tese (Doutorado em Química) - Universidade Federal de Goiás, Goiânia, 2017.http://repositorio.bc.ufg.br/tede/handle/tede/7922The chalcones are key intermediates for the biosynthesis of flavonoids and have shown an abundance of pharmacological effects including the antitumor effect. Thus, the synthesis and characterization of several chalcones and derivatives become important to develop a new class of compounds having antitumor activity. In the present work, the synthesis of chalcones, nitrochalcone sulfonamides and quinolinones was performed. By adjusting the reaction time and the sequence of the reactions, hybrids of open-chain chalcone sulfonamide whose molecular hybridization occurred at the ortho position of the benzoyl chalcone group through the Claisen- Schmidt condensation of acetophenone sulfonamide and nitrobenzaldehyde can be obtained at shorter reaction times, whereas quinolinone from cyclization at β carbon can be achieved if the reaction is stopped sequentially later. It is also noted that a novel structure, a chalcone (bis) sulfonamide, was prepared when chalcone was first synthesized and then reacted with benzenesulfonyl chloride. From the sulfonamide chalcones prepared with the m- aminoacetophenone sulfonamide and the o-, m- and p-nitrobenzaldehyde, a single product was formed. Among the 21 compounds prepared, five were ketone sulfonamides and sixteen were hybrid compounds (chalcones, chalcones, sulfonamides and quinolinones), which were purified by extraction, recrystallization and column chromatography and characterized by small molecule crystallography, melting point, Proton Nuclear Magnetic Resonance ( 1 H NMR) and infrared IV (IR). The antitumor activity was evaluated against three cancer cell lines: SF-295 (human glioblastoma), PC-3 (prostate) and HCT-116 (colon). Compounds 39, 40, 42, 43, 45a, 48a, 48b, 48c, 49 and 51 were cytotoxic to the three tumor cell lines tested. However, the quinolinones showed no relevant cytotoxic effect. It is also worth noting that compound 45a with a higher cytotoxic effect than doxorubicin, a drug used today against the three cancer cell lines evaluated, was a promising prototype for a new drug.As chalconas são compostos intermediários da biossíntese de flavonóides e têm demonstrado uma variedade de efeitos farmacológicos entre eles o efeito antitumoral. Assim a síntese e caracterização de várias chalconas e derivados se tornam importantes para o desenvolvimento de uma nova classe de compostos com atividade antitumoral. No presente trabalho foi realizada a síntese de chalcona, nitro chalconas sulfonamidas e quinolinonas. Ajustando o tempo e a ordem das reações, os híbridos de chalcona sulfonamida de cadeia aberta, cuja hibridação molecularocorreu na posição orto do grupo de chalcona benzoíla através da condensação Claisen-Schmidt da acetofenona sulfonamida e nitrobenzaldeído, podem ser obtidos em tempos de reação mais curtos, enquanto que a quinolinona proveniente da ciclização no carbono β pode ser alcançada se a reação for parada sequencialmente mais tarde. Destaca-se uma nova estrutura, uma chalcona (bis) sulfonamida, foi formada quando se sintetizou a chalcona primeiramente e então reagiu-a com o cloreto de benzenosulfonila. A partir das chalconas sulfonamidas preparadas com a m- aminoacetofenona sulfonamida e o o-, m- e p-nitrobenzaldeído, formou-se apenas um produto. Dos 21 compostos preparados 5 são cetonas-sulfonamidas e 16 compostos híbridos (chalconas, chalconas sulfonamidas e quinolinonas), que foram purificados por extração, recristalização e coluna de separação, e caracterizados por cristalografia de pequenas moléculas, ponto de fusão ressonância magnética de prótons ( 1 H-RMN) e infravermelho (IV). A atividade antitumoral foi avaliada frente a três linhagens de células cancerosas: SF-295 (glioblastoma - humano), PC-3 (próstata) e HCT-116 (colón). Os compostos 39, 40, 42, 43, 45a, 48a, 48b, 48c, 49 e 51, apresentaram citotoxicidade nas três linhagens de células tumorais testadas. Já as quinolinonas não apresentaram efeito citotóxico relevante. Destaca-se ainda que o composto 45a com maior efeito citotóxico do que a doxorrubicina, medicamento utilizado hoje contra as três linhagens celulares de câncer avaliadas, mostra-se como um promissor protótipo a um novo fármaco.Submitted by Luciana Ferreira (lucgeral@gmail.com) on 2017-10-30T10:24:52Z No. of bitstreams: 2 Tese - Mirian Rita Carrilho de Castro - 2017.pdf: 7039906 bytes, checksum: 5d352db979557bb35c672dba708ae0e8 (MD5) license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5)Approved for entry into archive by Luciana Ferreira (lucgeral@gmail.com) on 2017-10-30T10:26:18Z (GMT) No. of bitstreams: 2 Tese - Mirian Rita Carrilho de Castro - 2017.pdf: 7039906 bytes, checksum: 5d352db979557bb35c672dba708ae0e8 (MD5) license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5)Made available in DSpace on 2017-10-30T10:26:18Z (GMT). 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dc.title.eng.fl_str_mv |
Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas |
dc.title.alternative.eng.fl_str_mv |
Synthesis, physical chemical characterization and cytotoxic evaluation of chalcones, sulfonamid chalkones and quinolinones |
title |
Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas |
spellingShingle |
Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas Castro, Mirian Rita Carrilho de Chalcona sulfonamida Chalcone sulfonamide QUIMICA::QUIMICA ORGANICA |
title_short |
Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas |
title_full |
Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas |
title_fullStr |
Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas |
title_full_unstemmed |
Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas |
title_sort |
Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas |
author |
Castro, Mirian Rita Carrilho de |
author_facet |
Castro, Mirian Rita Carrilho de |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Noda Pérez, Caridad |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/8518548259609686 |
dc.contributor.advisor-co1.fl_str_mv |
Martins, Felipe Terra |
dc.contributor.advisor-co1Lattes.fl_str_mv |
http://lattes.cnpq.br/0466799995060671 |
dc.contributor.referee1.fl_str_mv |
Noda Pérez, Caridad |
dc.contributor.referee2.fl_str_mv |
Moraes, Manoel Odorico de |
dc.contributor.referee3.fl_str_mv |
Lee, Chen Chen |
dc.contributor.referee4.fl_str_mv |
Camargo, Ademir João |
dc.contributor.referee5.fl_str_mv |
Vaz, Boniek Gontijo |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/3395145363927567 |
dc.contributor.author.fl_str_mv |
Castro, Mirian Rita Carrilho de |
contributor_str_mv |
Noda Pérez, Caridad Martins, Felipe Terra Noda Pérez, Caridad Moraes, Manoel Odorico de Lee, Chen Chen Camargo, Ademir João Vaz, Boniek Gontijo |
dc.subject.por.fl_str_mv |
Chalcona sulfonamida |
topic |
Chalcona sulfonamida Chalcone sulfonamide QUIMICA::QUIMICA ORGANICA |
dc.subject.eng.fl_str_mv |
Chalcone sulfonamide |
dc.subject.cnpq.fl_str_mv |
QUIMICA::QUIMICA ORGANICA |
description |
The chalcones are key intermediates for the biosynthesis of flavonoids and have shown an abundance of pharmacological effects including the antitumor effect. Thus, the synthesis and characterization of several chalcones and derivatives become important to develop a new class of compounds having antitumor activity. In the present work, the synthesis of chalcones, nitrochalcone sulfonamides and quinolinones was performed. By adjusting the reaction time and the sequence of the reactions, hybrids of open-chain chalcone sulfonamide whose molecular hybridization occurred at the ortho position of the benzoyl chalcone group through the Claisen- Schmidt condensation of acetophenone sulfonamide and nitrobenzaldehyde can be obtained at shorter reaction times, whereas quinolinone from cyclization at β carbon can be achieved if the reaction is stopped sequentially later. It is also noted that a novel structure, a chalcone (bis) sulfonamide, was prepared when chalcone was first synthesized and then reacted with benzenesulfonyl chloride. From the sulfonamide chalcones prepared with the m- aminoacetophenone sulfonamide and the o-, m- and p-nitrobenzaldehyde, a single product was formed. Among the 21 compounds prepared, five were ketone sulfonamides and sixteen were hybrid compounds (chalcones, chalcones, sulfonamides and quinolinones), which were purified by extraction, recrystallization and column chromatography and characterized by small molecule crystallography, melting point, Proton Nuclear Magnetic Resonance ( 1 H NMR) and infrared IV (IR). The antitumor activity was evaluated against three cancer cell lines: SF-295 (human glioblastoma), PC-3 (prostate) and HCT-116 (colon). Compounds 39, 40, 42, 43, 45a, 48a, 48b, 48c, 49 and 51 were cytotoxic to the three tumor cell lines tested. However, the quinolinones showed no relevant cytotoxic effect. It is also worth noting that compound 45a with a higher cytotoxic effect than doxorubicin, a drug used today against the three cancer cell lines evaluated, was a promising prototype for a new drug. |
publishDate |
2017 |
dc.date.accessioned.fl_str_mv |
2017-10-30T10:26:18Z |
dc.date.issued.fl_str_mv |
2017-09-01 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
CASTRO, M. R. C. Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas. 2017. 206 f. Tese (Doutorado em Química) - Universidade Federal de Goiás, Goiânia, 2017. |
dc.identifier.uri.fl_str_mv |
http://repositorio.bc.ufg.br/tede/handle/tede/7922 |
identifier_str_mv |
CASTRO, M. R. C. Síntese, caracterização físico química e avaliação citotóxica de chalconas, chalconas sulfonamidas e quinolinonas. 2017. 206 f. Tese (Doutorado em Química) - Universidade Federal de Goiás, Goiânia, 2017. |
url |
http://repositorio.bc.ufg.br/tede/handle/tede/7922 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.program.fl_str_mv |
663693921325415158 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 |
dc.relation.department.fl_str_mv |
7826066743741197278 |
dc.relation.cnpq.fl_str_mv |
-8194069717282802154 |
dc.relation.sponsorship.fl_str_mv |
-961409807440757778 |
dc.rights.driver.fl_str_mv |
http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
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application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Goiás |
dc.publisher.program.fl_str_mv |
Programa de Pós-graduação em Química (IQ) |
dc.publisher.initials.fl_str_mv |
UFG |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Instituto de Química - IQ (RG) |
publisher.none.fl_str_mv |
Universidade Federal de Goiás |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional da UFG instname:Universidade Federal de Goiás (UFG) instacron:UFG |
instname_str |
Universidade Federal de Goiás (UFG) |
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UFG |
institution |
UFG |
reponame_str |
Repositório Institucional da UFG |
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Repositório Institucional da UFG |
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bitstream.checksum.fl_str_mv |
5d352db979557bb35c672dba708ae0e8 bd3efa91386c1718a7f26a329fdcb468 4afdbb8c545fd630ea7db775da747b2f d41d8cd98f00b204e9800998ecf8427e d41d8cd98f00b204e9800998ecf8427e |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 MD5 MD5 |
repository.name.fl_str_mv |
Repositório Institucional da UFG - Universidade Federal de Goiás (UFG) |
repository.mail.fl_str_mv |
tasesdissertacoes.bc@ufg.br |
_version_ |
1798044410725793792 |