Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFG |
Texto Completo: | http://repositorio.bc.ufg.br/tede/handle/tede/9774 |
Resumo: | In the present work the synthesis, characterization of seven symmetric bischalcones, of which two are unpublished, and the structural elucidation by means of the crystallography of one of them, besides the cytotoxic analysis of all the compounds against 3 different lines of cancer. After synthesizing the compounds were characterized by 1 H Nuclear Magnetic Resonance (NMR), melting point, infrared (IR), Mass Spectrometry (MS) and elemental analysis of C and H (CHN). The compounds were obtained by the reaction of aldol condensation between the acetone and the benzaldehydes for substituted, in a yield of between 81.19 and 26.92%. The results of 1 H NMR, MS and CHN analyzes confirmed that the expected compounds were obtained in high purity. The crystallographic study was chosen as a technique to elucidate crystalline structure because it has been shown to be of fundamental importance to know the molecular arrangement and thus serving as an important tool for pharmacology and other related areas. The data of the unpublished molecule were obtained by X-ray diffraction of monocrystal, thus allowing to evaluate the geometric parameters, the distances and the interatomic angles, intermolecular interactions and the supramolecular arrangement. The selected crystal crystallized in the monoclinic system with four symmetry operations and a 50% disorder in two of its atoms, its interatomic distances and its binding angles were measured and compared with structures previously deposited in the Cambridge Crystallographic Data Center (CCDC). With the aid of 13 C solid-state nuclear magnetic resonance (NMR-s) and theoretical energy analysis, the presence of the mixed anti-syn confomer was detected. Considering the great advance in the studies of bischalcone and its potential tumor inhibitor, these compounds were sent to the Nucleus of Research and Development of Medicines (NRDM) of the Federal University of Ceará (UFC), with the purpose of evaluating its antitumor activity against the human cancer cells (SNB-19) (glioblastoma), PC-3 (prostate) and HCT-116 (colon), obtaining values of inhibition of growth in the 11% to 100%, and the ability to inhibit (IC 50 ) 50% of cell proliferation from 0.48 to 13.17 μg.ml -1 , the best compound being the 5. |
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Noda Pérez, Caridadhttp://lattes.cnpq.br/7849604313803596Martins, Felipe Terrahttp://lattes.cnpq.br/0466799995060671Noda Pérez, CaridadLariucci, CarlitoCosta, Maísa Borgeshttp://lattes.cnpq.br/7849604313803596Almeida, Lívia Oliveira Alves Ferreira de2019-07-02T14:26:20Z2019-06-07FERREIRA, L. O. A. Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas. 2019. 64 f. Dissertação (Mestrado em Química) - Universidade Federal de Goiás, Goiânia, 2019.http://repositorio.bc.ufg.br/tede/handle/tede/9774ark:/38995/001300000886vIn the present work the synthesis, characterization of seven symmetric bischalcones, of which two are unpublished, and the structural elucidation by means of the crystallography of one of them, besides the cytotoxic analysis of all the compounds against 3 different lines of cancer. After synthesizing the compounds were characterized by 1 H Nuclear Magnetic Resonance (NMR), melting point, infrared (IR), Mass Spectrometry (MS) and elemental analysis of C and H (CHN). The compounds were obtained by the reaction of aldol condensation between the acetone and the benzaldehydes for substituted, in a yield of between 81.19 and 26.92%. The results of 1 H NMR, MS and CHN analyzes confirmed that the expected compounds were obtained in high purity. The crystallographic study was chosen as a technique to elucidate crystalline structure because it has been shown to be of fundamental importance to know the molecular arrangement and thus serving as an important tool for pharmacology and other related areas. The data of the unpublished molecule were obtained by X-ray diffraction of monocrystal, thus allowing to evaluate the geometric parameters, the distances and the interatomic angles, intermolecular interactions and the supramolecular arrangement. The selected crystal crystallized in the monoclinic system with four symmetry operations and a 50% disorder in two of its atoms, its interatomic distances and its binding angles were measured and compared with structures previously deposited in the Cambridge Crystallographic Data Center (CCDC). With the aid of 13 C solid-state nuclear magnetic resonance (NMR-s) and theoretical energy analysis, the presence of the mixed anti-syn confomer was detected. Considering the great advance in the studies of bischalcone and its potential tumor inhibitor, these compounds were sent to the Nucleus of Research and Development of Medicines (NRDM) of the Federal University of Ceará (UFC), with the purpose of evaluating its antitumor activity against the human cancer cells (SNB-19) (glioblastoma), PC-3 (prostate) and HCT-116 (colon), obtaining values of inhibition of growth in the 11% to 100%, and the ability to inhibit (IC 50 ) 50% of cell proliferation from 0.48 to 13.17 μg.ml -1 , the best compound being the 5.No presente trabalho foi feita a síntese, caracterização de sete bischalconas simétricas, das quais duas são inéditas, e a elucidação estrutural por meio da cristalografia de uma delas, além da análise cito toxicológica de todos os compostos contra 3 linhagens diferentes de câncer. Após sintetizados os compostos foram caracterizados por Ressonância Magnética Nuclear (RMN) de 1 H, ponto de fusão, infravermelho (IV), Espectrometria de Massas (EM) e análise elementar de C e H (CHN). Os compostos foram obtidos pela reação de condensação aldólica entre a acetona e os benzaldeídos para substituídos, com rendimento entre 81,19 e 26,92%. Os resultados das análises de RMN de 1 H, EM e CHN confirmaram que foram obtidosos compostos esperados com elevada pureza. O estudo cristalográfico foi escolhido como técnica para elucidação da estrutura cristalina pois vem mostrando ser de fundamental importância para conhecer o arranjo molecular e assim servindo como uma ferramenta importantíssima para a farmacologia e demais áreas afins. Os dados da molécula inédita foram obtidos por difração de Raios X de monocristal, assim permitindo avaliar os parâmetros geométricos, as distâncias e os ângulos interatômicos, interações intermoleculares e o arranjo supramolecular. O cristal selecionado cristalizou-se no sistema monoclínico com quatro operações de simetria e uma desordem de 50% em dois de seus átomos, suas distâncias interatômicas e seus ângulos de ligação foram medidos e comparados com estruturas previamente depositadas no banco de dados Cambridge Crystallographic Data Center (CCDC). Com auxílio da Ressonância Magnética Nuclear no estado sólido (RMN-s) de 13 C e análise teórica de energia detectou-se a presença do confôrmero misto anti-syn. Considerando o grande avanço nos estudos das bischalconas e no seu potencial inibidor tumoral esses compostos foram enviados para o Núcleo de Pesquisas e Desenvolvimento de Medicamentos (NPDM) da Universidade Federal do Ceará (UFC), com o intuito de avaliar sua atividade antitumoral contra células de câncer humano, linhagens SNB-19 (glioblastoma), PC-3 (próstata) e HCT-116 (colon), obtendo valores de inibição de crescimento na faixa de 11% a 100% e em relação a capacidade de inibir (CI 50 ) de 50% da proliferação celular de 0,48 a 13,17 μg.ml -1 , sendo o melhor composto o 5.Submitted by Luciana Ferreira (lucgeral@gmail.com) on 2019-07-02T14:15:08Z No. of bitstreams: 2 Dissertação - Lívia Oliveira Alves Ferreira de Almeida - 2019.pdf: 3399574 bytes, checksum: 3e355e8197c71adc42b2ed4f832d2ce3 (MD5) license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5)Approved for entry into archive by Luciana Ferreira (lucgeral@gmail.com) on 2019-07-02T14:26:20Z (GMT) No. of bitstreams: 2 Dissertação - Lívia Oliveira Alves Ferreira de Almeida - 2019.pdf: 3399574 bytes, checksum: 3e355e8197c71adc42b2ed4f832d2ce3 (MD5) license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5)Made available in DSpace on 2019-07-02T14:26:20Z (GMT). No. of bitstreams: 2 Dissertação - Lívia Oliveira Alves Ferreira de Almeida - 2019.pdf: 3399574 bytes, checksum: 3e355e8197c71adc42b2ed4f832d2ce3 (MD5) license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5) Previous issue date: 2019-06-07Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESapplication/pdfporUniversidade Federal de GoiásPrograma de Pós-graduação em Química (IQ)UFGBrasilInstituto de Química - IQ (RG)http://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessBischalconas simétricasAntitumoraisCristalografiaSymmetrical bischalconesAntitumoralsCrystallographyCIENCIAS EXATAS E DA TERRA::QUIMICASíntese, caracterização físico-química e elucidação estrutural de bischalconas simétricasSynthesis, physico-chemical characterization and structural elucidation of symmetric bischalconesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesis663693921325415158600600600600782606674374119727815717003253031171952075167498588264571reponame:Repositório Institucional da UFGinstname:Universidade Federal de Goiás (UFG)instacron:UFGCC-LICENSElicense_urllicense_urltext/plain; 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dc.title.eng.fl_str_mv |
Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas |
dc.title.alternative.eng.fl_str_mv |
Synthesis, physico-chemical characterization and structural elucidation of symmetric bischalcones |
title |
Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas |
spellingShingle |
Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas Almeida, Lívia Oliveira Alves Ferreira de Bischalconas simétricas Antitumorais Cristalografia Symmetrical bischalcones Antitumorals Crystallography CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas |
title_full |
Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas |
title_fullStr |
Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas |
title_full_unstemmed |
Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas |
title_sort |
Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas |
author |
Almeida, Lívia Oliveira Alves Ferreira de |
author_facet |
Almeida, Lívia Oliveira Alves Ferreira de |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Noda Pérez, Caridad |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7849604313803596 |
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 |
Lariucci, Carlito |
dc.contributor.referee3.fl_str_mv |
Costa, Maísa Borges |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/7849604313803596 |
dc.contributor.author.fl_str_mv |
Almeida, Lívia Oliveira Alves Ferreira de |
contributor_str_mv |
Noda Pérez, Caridad Martins, Felipe Terra Noda Pérez, Caridad Lariucci, Carlito Costa, Maísa Borges |
dc.subject.por.fl_str_mv |
Bischalconas simétricas Antitumorais Cristalografia |
topic |
Bischalconas simétricas Antitumorais Cristalografia Symmetrical bischalcones Antitumorals Crystallography CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Symmetrical bischalcones Antitumorals Crystallography |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In the present work the synthesis, characterization of seven symmetric bischalcones, of which two are unpublished, and the structural elucidation by means of the crystallography of one of them, besides the cytotoxic analysis of all the compounds against 3 different lines of cancer. After synthesizing the compounds were characterized by 1 H Nuclear Magnetic Resonance (NMR), melting point, infrared (IR), Mass Spectrometry (MS) and elemental analysis of C and H (CHN). The compounds were obtained by the reaction of aldol condensation between the acetone and the benzaldehydes for substituted, in a yield of between 81.19 and 26.92%. The results of 1 H NMR, MS and CHN analyzes confirmed that the expected compounds were obtained in high purity. The crystallographic study was chosen as a technique to elucidate crystalline structure because it has been shown to be of fundamental importance to know the molecular arrangement and thus serving as an important tool for pharmacology and other related areas. The data of the unpublished molecule were obtained by X-ray diffraction of monocrystal, thus allowing to evaluate the geometric parameters, the distances and the interatomic angles, intermolecular interactions and the supramolecular arrangement. The selected crystal crystallized in the monoclinic system with four symmetry operations and a 50% disorder in two of its atoms, its interatomic distances and its binding angles were measured and compared with structures previously deposited in the Cambridge Crystallographic Data Center (CCDC). With the aid of 13 C solid-state nuclear magnetic resonance (NMR-s) and theoretical energy analysis, the presence of the mixed anti-syn confomer was detected. Considering the great advance in the studies of bischalcone and its potential tumor inhibitor, these compounds were sent to the Nucleus of Research and Development of Medicines (NRDM) of the Federal University of Ceará (UFC), with the purpose of evaluating its antitumor activity against the human cancer cells (SNB-19) (glioblastoma), PC-3 (prostate) and HCT-116 (colon), obtaining values of inhibition of growth in the 11% to 100%, and the ability to inhibit (IC 50 ) 50% of cell proliferation from 0.48 to 13.17 μg.ml -1 , the best compound being the 5. |
publishDate |
2019 |
dc.date.accessioned.fl_str_mv |
2019-07-02T14:26:20Z |
dc.date.issued.fl_str_mv |
2019-06-07 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
FERREIRA, L. O. A. Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas. 2019. 64 f. Dissertação (Mestrado em Química) - Universidade Federal de Goiás, Goiânia, 2019. |
dc.identifier.uri.fl_str_mv |
http://repositorio.bc.ufg.br/tede/handle/tede/9774 |
dc.identifier.dark.fl_str_mv |
ark:/38995/001300000886v |
identifier_str_mv |
FERREIRA, L. O. A. Síntese, caracterização físico-química e elucidação estrutural de bischalconas simétricas. 2019. 64 f. Dissertação (Mestrado em Química) - Universidade Federal de Goiás, Goiânia, 2019. ark:/38995/001300000886v |
url |
http://repositorio.bc.ufg.br/tede/handle/tede/9774 |
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 |
1571700325303117195 |
dc.relation.sponsorship.fl_str_mv |
2075167498588264571 |
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 |
dc.format.none.fl_str_mv |
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) |
instacron_str |
UFG |
institution |
UFG |
reponame_str |
Repositório Institucional da UFG |
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Repositório Institucional da UFG |
bitstream.url.fl_str_mv |
http://repositorio.bc.ufg.br/tede/bitstreams/e75e9a85-49d1-45f6-83ce-e87c838da4c9/download http://repositorio.bc.ufg.br/tede/bitstreams/3c95afb4-d985-4efc-906d-8ba538f5882c/download http://repositorio.bc.ufg.br/tede/bitstreams/e399b1b6-4289-47db-bb0c-19c81f8c96fe/download http://repositorio.bc.ufg.br/tede/bitstreams/25f8671b-113d-481b-8c82-d4eb78ca4270/download http://repositorio.bc.ufg.br/tede/bitstreams/c09c9648-45df-474b-9ed4-1680b16e6c3c/download |
bitstream.checksum.fl_str_mv |
4afdbb8c545fd630ea7db775da747b2f d41d8cd98f00b204e9800998ecf8427e d41d8cd98f00b204e9800998ecf8427e bd3efa91386c1718a7f26a329fdcb468 3e355e8197c71adc42b2ed4f832d2ce3 |
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_ |
1811721447332118528 |