S?ntese de Biginelli aplicada ao desenvolvimento de novas cumarino-Diidropirimidinonas com potencial uso no diagn?stico e tratamento de c?nceres associados ? HSP 90
Autor(a) principal: | |
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Data de Publicação: | 2015 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFRRJ |
Texto Completo: | https://tede.ufrrj.br/jspui/handle/jspui/2892 |
Resumo: | Cancer is a term used for diseases in which abnormal cells divide without control and are able to invade other tissues and can be spread to distant locations in the body through blood and lymph systems through a process known as metastasis, been considered by the World Health Organization as one of the biggest health problems facing humanity at this century. Hsp90 (Heat Shock Proteins ? 90kD) is considered today as one possible therapeutic target in cancer treatment. This enzyme has an important role in the development of tumor cells processes because it is stable, and is present in all organelles, corresponding to 1-2% of the cellular protein content, reaching to 6% stress in stress level. Thus, this work proposes the design and synthesis of a series of novobiocin (24) analogs, and it is known as inhibitor of this enzyme. The molecules described herein belong to the class of dihydropyrimidin-2(1H)-one and was designed by molecular hybridization of this core with coumarin subunit of novobiocin, both compounds have proved activity on tumor cell lines. Therefore this work aims to study the process of synthesis of diidropirimidin-2(1H)-ones planned as inhibitors of Hsp90, its reaction scope and evaluate their fluorescence properties as possible cellular markers. The series was synthesized by multicomponent Biginelli reaction, using ureas (50a-b), aromatic aldehydes (Ar a-n), coumarin beta-ketoesters previously synthesized (105a-b) and HCl as catalyst. All compounds were characterized by physical and chemical methods of analysis. This is the first report of Biginelli adducts bearing a coumarin nucleus in the ?-ketoester moiety and their MCR mechanism seems to pass through a Knoevenagel intermediate, which was considered as unlikely before. A chemical library of dihydropyrimidin-2(1H)-one was obtained with low to excellent yields (25-99%), with its final structure confirmed also by studies of X-ray diffraction. Photophysical analyses of representative compounds in different solvents show good Stokes shifts in water that are associated to a postulated ICT process which, along with the determination of their pKa, make these compounds a good start point for new chemical and biological probes as well as useful pH indicators. |
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K?mmerle, Arthur Eugen053.978.487-78Graebin, Cedric Stephan966.049.800-49K?mmerle, Arthur EugenGraebin, Cedric StephanLacerda, Renata BarbosaBarbosa, Maria Let?cia de CastroFerreira, Aur?lio Baird Buarque124.035.327-89Ribeiro, Felipe Vit?rio2019-09-13T18:16:59Z2015-05-06RIBEIRO, Felipe Vit?rio. S?ntese de Biginelli aplicada ao desenvolvimento de novas cumarino-Diidropirimidinonas com potencial uso no diagn?stico e tratamento de c?nceres associados ? HSP 90. 2015. 210 f. Disserta??o (Mestrado em Qu?mica). Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, RJ, 2015.https://tede.ufrrj.br/jspui/handle/jspui/2892Cancer is a term used for diseases in which abnormal cells divide without control and are able to invade other tissues and can be spread to distant locations in the body through blood and lymph systems through a process known as metastasis, been considered by the World Health Organization as one of the biggest health problems facing humanity at this century. Hsp90 (Heat Shock Proteins ? 90kD) is considered today as one possible therapeutic target in cancer treatment. This enzyme has an important role in the development of tumor cells processes because it is stable, and is present in all organelles, corresponding to 1-2% of the cellular protein content, reaching to 6% stress in stress level. Thus, this work proposes the design and synthesis of a series of novobiocin (24) analogs, and it is known as inhibitor of this enzyme. The molecules described herein belong to the class of dihydropyrimidin-2(1H)-one and was designed by molecular hybridization of this core with coumarin subunit of novobiocin, both compounds have proved activity on tumor cell lines. Therefore this work aims to study the process of synthesis of diidropirimidin-2(1H)-ones planned as inhibitors of Hsp90, its reaction scope and evaluate their fluorescence properties as possible cellular markers. The series was synthesized by multicomponent Biginelli reaction, using ureas (50a-b), aromatic aldehydes (Ar a-n), coumarin beta-ketoesters previously synthesized (105a-b) and HCl as catalyst. All compounds were characterized by physical and chemical methods of analysis. This is the first report of Biginelli adducts bearing a coumarin nucleus in the ?-ketoester moiety and their MCR mechanism seems to pass through a Knoevenagel intermediate, which was considered as unlikely before. A chemical library of dihydropyrimidin-2(1H)-one was obtained with low to excellent yields (25-99%), with its final structure confirmed also by studies of X-ray diffraction. Photophysical analyses of representative compounds in different solvents show good Stokes shifts in water that are associated to a postulated ICT process which, along with the determination of their pKa, make these compounds a good start point for new chemical and biological probes as well as useful pH indicators.C?ncer ? um termo usado para doen?as em que c?lulas anormais se dividem sem controle e s?o capazes de invadir outros tecidos, podendo se espalhar para lugares distantes no corpo atrav?s dos sistemas sangu?neos e linf?ticos por um processo conhecido como met?stase, sendo considerado pela Organiza??o Mundial da Sa?de um dos maiores problemas de sa?de enfrentados pela humanidade neste s?culo. A Hsp90 (Heat Shock Proteins ? 90kD) ? considerada hoje como um poss?vel alvo terap?utico no tratamento contra o c?ncer. Esta enzima possui um papel muito importante no desenvolvimento de processos tumorais das c?lulas porque a mesma est? presente em todas as organelas e ? est?vel, al?m de corresponder a 1-2% do conte?do prot?ico celular, podendo chegar a 6% em n?vel de estresse. Dessa forma, a presente disserta??o prop?e o planejamento e a s?ntese de uma s?rie de an?logos ao novobiocin (24), pois ? um inibidor desta enzima j? descrito na literatura. A s?rie aqui descrita ? da classe das diidropirimidin-2(1H)-onas e foi planejada atrav?s de hibrida??o molecular deste n?cleo com a subunidade cumar?nica do novobiocin. Ambos os n?cleos s?o comprovadamente ativos sobre linhagens de c?lulas tumorais. Portanto este trabalho tem como objetivo estudar o processo de s?ntese das diidropirimidin-2(1H)-onas planejadas como inibidoras da Hsp90, seu escopo reacional e avaliar suas propriedades de fluoresc?ncia como poss?veis marcadores celulares. A s?rie foi sintetizada atrav?s da rea??o multicomponente de Biginelli, utilizando ureias (50a-b), alde?dos arom?ticos (Ar a-n), beta-ceto?steres cumar?nicos sintetizados previamente (105a-b), HCl como catalisador. Toda a s?rie foi caracterizada por m?todos f?sicos e qu?micos de an?lise. Este ? o primeiro relato de adutos de Biginelli contendo um n?cleo cumar?nico e o seu mecanismo reacional multicomponente parece curiosamente passar atrav?s de um intermedi?rio de Knoevenagel, que foi considerado improv?vel pela literatura. A biblioteca de diidropirimidin-2(1H)-onas foi obtida com rendimentos de baixos a excelentes (25-99%), tendo sua estrutura final confirmada, tamb?m, por estudos de difra??o de raios-X. An?lises fotof?sicas de alguns compostos, em diferentes solventes, mostraram bons deslocamentos de Stokes em ?gua, que est?o associados a um processo conhecido como transfer?ncia interna de carga (ICT) que, junto com a determina??o de seu pKa, fazem destes compostos um bom ponto de partida para novas sondas qu?micas e biol?gicas, bem como indicadores de pH.Submitted by Jorge Silva (jorgelmsilva@ufrrj.br) on 2019-09-13T18:16:59Z No. of bitstreams: 1 2015 - Felipe Vit?rio Ribeiro.pdf: 10018372 bytes, checksum: 7bbb4096b83baec2c905b56b06613158 (MD5)Made available in DSpace on 2019-09-13T18:16:59Z (GMT). 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HSP 90info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFRRJinstname:Universidade Federal Rural do Rio de Janeiro (UFRRJ)instacron:UFRRJTHUMBNAIL2015 - Felipe Vit?rio Ribeiro.pdf.jpg2015 - Felipe Vit?rio Ribeiro.pdf.jpgimage/jpeg1949http://localhost:8080/tede/bitstream/jspui/2892/18/2015+-+Felipe+Vit%C3%B3rio+Ribeiro.pdf.jpg5709f16d7bda3c6b37000e61e705ef78MD518TEXT2015 - Felipe Vit?rio Ribeiro.pdf.txt2015 - Felipe Vit?rio Ribeiro.pdf.txttext/plain170144http://localhost:8080/tede/bitstream/jspui/2892/17/2015+-+Felipe+Vit%C3%B3rio+Ribeiro.pdf.txt0427ada47db414a8d4caa3752c34f501MD517ORIGINAL2015 - Felipe Vit?rio Ribeiro.pdf2015 - Felipe Vit?rio Ribeiro.pdfapplication/pdf10018372http://localhost:8080/tede/bitstream/jspui/2892/2/2015+-+Felipe+Vit%C3%B3rio+Ribeiro.pdf7bbb4096b83baec2c905b56b06613158MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-82089http://localhost:8080/tede/bitstream/jspui/2892/1/license.txt7b5ba3d2445355f386edab96125d42b7MD51jspui/28922022-02-11 09:03:06.987oai:localhost: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Biblioteca Digital de Teses e Dissertaçõeshttps://tede.ufrrj.br/PUBhttps://tede.ufrrj.br/oai/requestbibliot@ufrrj.br||bibliot@ufrrj.bropendoar:2022-02-11T11:03:06Biblioteca Digital de Teses e Dissertações da UFRRJ - Universidade Federal Rural do Rio de Janeiro (UFRRJ)false |
dc.title.por.fl_str_mv |
S?ntese de Biginelli aplicada ao desenvolvimento de novas cumarino-Diidropirimidinonas com potencial uso no diagn?stico e tratamento de c?nceres associados ? HSP 90 |
title |
S?ntese de Biginelli aplicada ao desenvolvimento de novas cumarino-Diidropirimidinonas com potencial uso no diagn?stico e tratamento de c?nceres associados ? HSP 90 |
spellingShingle |
S?ntese de Biginelli aplicada ao desenvolvimento de novas cumarino-Diidropirimidinonas com potencial uso no diagn?stico e tratamento de c?nceres associados ? HSP 90 Ribeiro, Felipe Vit?rio C?ncer diidropirimidin-2(1H)-onas, Hsp-90 novobiocin rea??o multicomponente de Biginelli Qu?mica |
title_short |
S?ntese de Biginelli aplicada ao desenvolvimento de novas cumarino-Diidropirimidinonas com potencial uso no diagn?stico e tratamento de c?nceres associados ? HSP 90 |
title_full |
S?ntese de Biginelli aplicada ao desenvolvimento de novas cumarino-Diidropirimidinonas com potencial uso no diagn?stico e tratamento de c?nceres associados ? HSP 90 |
title_fullStr |
S?ntese de Biginelli aplicada ao desenvolvimento de novas cumarino-Diidropirimidinonas com potencial uso no diagn?stico e tratamento de c?nceres associados ? HSP 90 |
title_full_unstemmed |
S?ntese de Biginelli aplicada ao desenvolvimento de novas cumarino-Diidropirimidinonas com potencial uso no diagn?stico e tratamento de c?nceres associados ? HSP 90 |
title_sort |
S?ntese de Biginelli aplicada ao desenvolvimento de novas cumarino-Diidropirimidinonas com potencial uso no diagn?stico e tratamento de c?nceres associados ? HSP 90 |
author |
Ribeiro, Felipe Vit?rio |
author_facet |
Ribeiro, Felipe Vit?rio |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
K?mmerle, Arthur Eugen |
dc.contributor.advisor1ID.fl_str_mv |
053.978.487-78 |
dc.contributor.advisor-co1.fl_str_mv |
Graebin, Cedric Stephan |
dc.contributor.advisor-co1ID.fl_str_mv |
966.049.800-49 |
dc.contributor.referee1.fl_str_mv |
K?mmerle, Arthur Eugen |
dc.contributor.referee2.fl_str_mv |
Graebin, Cedric Stephan |
dc.contributor.referee3.fl_str_mv |
Lacerda, Renata Barbosa |
dc.contributor.referee4.fl_str_mv |
Barbosa, Maria Let?cia de Castro |
dc.contributor.referee5.fl_str_mv |
Ferreira, Aur?lio Baird Buarque |
dc.contributor.authorID.fl_str_mv |
124.035.327-89 |
dc.contributor.author.fl_str_mv |
Ribeiro, Felipe Vit?rio |
contributor_str_mv |
K?mmerle, Arthur Eugen Graebin, Cedric Stephan K?mmerle, Arthur Eugen Graebin, Cedric Stephan Lacerda, Renata Barbosa Barbosa, Maria Let?cia de Castro Ferreira, Aur?lio Baird Buarque |
dc.subject.por.fl_str_mv |
C?ncer diidropirimidin-2(1H)-onas, Hsp-90 novobiocin rea??o multicomponente de Biginelli |
topic |
C?ncer diidropirimidin-2(1H)-onas, Hsp-90 novobiocin rea??o multicomponente de Biginelli Qu?mica |
dc.subject.cnpq.fl_str_mv |
Qu?mica |
description |
Cancer is a term used for diseases in which abnormal cells divide without control and are able to invade other tissues and can be spread to distant locations in the body through blood and lymph systems through a process known as metastasis, been considered by the World Health Organization as one of the biggest health problems facing humanity at this century. Hsp90 (Heat Shock Proteins ? 90kD) is considered today as one possible therapeutic target in cancer treatment. This enzyme has an important role in the development of tumor cells processes because it is stable, and is present in all organelles, corresponding to 1-2% of the cellular protein content, reaching to 6% stress in stress level. Thus, this work proposes the design and synthesis of a series of novobiocin (24) analogs, and it is known as inhibitor of this enzyme. The molecules described herein belong to the class of dihydropyrimidin-2(1H)-one and was designed by molecular hybridization of this core with coumarin subunit of novobiocin, both compounds have proved activity on tumor cell lines. Therefore this work aims to study the process of synthesis of diidropirimidin-2(1H)-ones planned as inhibitors of Hsp90, its reaction scope and evaluate their fluorescence properties as possible cellular markers. The series was synthesized by multicomponent Biginelli reaction, using ureas (50a-b), aromatic aldehydes (Ar a-n), coumarin beta-ketoesters previously synthesized (105a-b) and HCl as catalyst. All compounds were characterized by physical and chemical methods of analysis. This is the first report of Biginelli adducts bearing a coumarin nucleus in the ?-ketoester moiety and their MCR mechanism seems to pass through a Knoevenagel intermediate, which was considered as unlikely before. A chemical library of dihydropyrimidin-2(1H)-one was obtained with low to excellent yields (25-99%), with its final structure confirmed also by studies of X-ray diffraction. Photophysical analyses of representative compounds in different solvents show good Stokes shifts in water that are associated to a postulated ICT process which, along with the determination of their pKa, make these compounds a good start point for new chemical and biological probes as well as useful pH indicators. |
publishDate |
2015 |
dc.date.issued.fl_str_mv |
2015-05-06 |
dc.date.accessioned.fl_str_mv |
2019-09-13T18:16:59Z |
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 |
RIBEIRO, Felipe Vit?rio. S?ntese de Biginelli aplicada ao desenvolvimento de novas cumarino-Diidropirimidinonas com potencial uso no diagn?stico e tratamento de c?nceres associados ? HSP 90. 2015. 210 f. Disserta??o (Mestrado em Qu?mica). Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, RJ, 2015. |
dc.identifier.uri.fl_str_mv |
https://tede.ufrrj.br/jspui/handle/jspui/2892 |
identifier_str_mv |
RIBEIRO, Felipe Vit?rio. S?ntese de Biginelli aplicada ao desenvolvimento de novas cumarino-Diidropirimidinonas com potencial uso no diagn?stico e tratamento de c?nceres associados ? HSP 90. 2015. 210 f. Disserta??o (Mestrado em Qu?mica). Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica, RJ, 2015. |
url |
https://tede.ufrrj.br/jspui/handle/jspui/2892 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal Rural do Rio de Janeiro |
dc.publisher.program.fl_str_mv |
Programa de P?s-Gradua??o em Qu?mica |
dc.publisher.initials.fl_str_mv |
UFRRJ |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Instituto de Ci?ncias Exatas |
publisher.none.fl_str_mv |
Universidade Federal Rural do Rio de Janeiro |
dc.source.none.fl_str_mv |
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Universidade Federal Rural do Rio de Janeiro (UFRRJ) |
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UFRRJ |
institution |
UFRRJ |
reponame_str |
Biblioteca Digital de Teses e Dissertações da UFRRJ |
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Biblioteca Digital de Teses e Dissertações da UFRRJ |
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Biblioteca Digital de Teses e Dissertações da UFRRJ - Universidade Federal Rural do Rio de Janeiro (UFRRJ) |
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