Synthetic studies on a novel celastrol- fluo-rescent probe for in vivo imaging and novel amination methodologies
Autor(a) principal: | |
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Data de Publicação: | 2017 |
Tipo de documento: | Dissertação |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10362/25873 |
Resumo: | This dissertation was divided into two parts: Part 1 A novel methodology of aminomethylation of alkenes and alkynes was studied. The methodology developed involved the use of TFA to promote iminium formation from tetramethyldiaminomethane, which in turn reacts with a nucleophilic double bond to deliver an amine. A very well-rounded scope was accomplished with examples that range from aliphatic, cyclic and aromatic alkenes. Functional group tolerance was also pursuit with the method showing a great tolerance towards commonly used groups such as halides and esters. A total number of 25 boc-protected amines were synthesized using alkenes with yields up 82 %. Part 2 The second part consisted on the development of a fluorescence probe using a fla-vylium ion for in vivo imaging. In order to develop a fluorescent system that could be used in in vivo imaging for detection cancer cells, the prepared flavilyum was coupled with the theraupeutical relevant Celastrol. A new flavilyum ion was synthesized via condensation of a 7-diethylaminophenol with acetophenone possessing an halogenated alkylic linker at the 4’ position. Different pathways were investigated in order to reach and optimize the synthesis of a C4 functionalized flavylium salt that was prepared in three steps. Attempts were performed to couple the prepared flavylium to Celastrol. |
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Synthetic studies on a novel celastrol- fluo-rescent probe for in vivo imaging and novel amination methodologiesAminomethylationAmine synthesisUnactivated AlkenesFlavylium coumpoundssynthesis of fluorescent compoundscelastrolDomínio/Área Científica::Engenharia e Tecnologia::Engenharia QuímicaThis dissertation was divided into two parts: Part 1 A novel methodology of aminomethylation of alkenes and alkynes was studied. The methodology developed involved the use of TFA to promote iminium formation from tetramethyldiaminomethane, which in turn reacts with a nucleophilic double bond to deliver an amine. A very well-rounded scope was accomplished with examples that range from aliphatic, cyclic and aromatic alkenes. Functional group tolerance was also pursuit with the method showing a great tolerance towards commonly used groups such as halides and esters. A total number of 25 boc-protected amines were synthesized using alkenes with yields up 82 %. Part 2 The second part consisted on the development of a fluorescence probe using a fla-vylium ion for in vivo imaging. In order to develop a fluorescent system that could be used in in vivo imaging for detection cancer cells, the prepared flavilyum was coupled with the theraupeutical relevant Celastrol. A new flavilyum ion was synthesized via condensation of a 7-diethylaminophenol with acetophenone possessing an halogenated alkylic linker at the 4’ position. Different pathways were investigated in order to reach and optimize the synthesis of a C4 functionalized flavylium salt that was prepared in three steps. Attempts were performed to couple the prepared flavylium to Celastrol.Marques, Maria ManuelMaulide, NunoRUNGonçalves, Carlos Rafael Costa2021-01-21T01:30:18Z2017-112017-112017-11-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfhttp://hdl.handle.net/10362/25873enginfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-03-11T04:13:37Zoai:run.unl.pt:10362/25873Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:28:23.819942Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Synthetic studies on a novel celastrol- fluo-rescent probe for in vivo imaging and novel amination methodologies |
title |
Synthetic studies on a novel celastrol- fluo-rescent probe for in vivo imaging and novel amination methodologies |
spellingShingle |
Synthetic studies on a novel celastrol- fluo-rescent probe for in vivo imaging and novel amination methodologies Gonçalves, Carlos Rafael Costa Aminomethylation Amine synthesis Unactivated Alkenes Flavylium coumpounds synthesis of fluorescent compounds celastrol Domínio/Área Científica::Engenharia e Tecnologia::Engenharia Química |
title_short |
Synthetic studies on a novel celastrol- fluo-rescent probe for in vivo imaging and novel amination methodologies |
title_full |
Synthetic studies on a novel celastrol- fluo-rescent probe for in vivo imaging and novel amination methodologies |
title_fullStr |
Synthetic studies on a novel celastrol- fluo-rescent probe for in vivo imaging and novel amination methodologies |
title_full_unstemmed |
Synthetic studies on a novel celastrol- fluo-rescent probe for in vivo imaging and novel amination methodologies |
title_sort |
Synthetic studies on a novel celastrol- fluo-rescent probe for in vivo imaging and novel amination methodologies |
author |
Gonçalves, Carlos Rafael Costa |
author_facet |
Gonçalves, Carlos Rafael Costa |
author_role |
author |
dc.contributor.none.fl_str_mv |
Marques, Maria Manuel Maulide, Nuno RUN |
dc.contributor.author.fl_str_mv |
Gonçalves, Carlos Rafael Costa |
dc.subject.por.fl_str_mv |
Aminomethylation Amine synthesis Unactivated Alkenes Flavylium coumpounds synthesis of fluorescent compounds celastrol Domínio/Área Científica::Engenharia e Tecnologia::Engenharia Química |
topic |
Aminomethylation Amine synthesis Unactivated Alkenes Flavylium coumpounds synthesis of fluorescent compounds celastrol Domínio/Área Científica::Engenharia e Tecnologia::Engenharia Química |
description |
This dissertation was divided into two parts: Part 1 A novel methodology of aminomethylation of alkenes and alkynes was studied. The methodology developed involved the use of TFA to promote iminium formation from tetramethyldiaminomethane, which in turn reacts with a nucleophilic double bond to deliver an amine. A very well-rounded scope was accomplished with examples that range from aliphatic, cyclic and aromatic alkenes. Functional group tolerance was also pursuit with the method showing a great tolerance towards commonly used groups such as halides and esters. A total number of 25 boc-protected amines were synthesized using alkenes with yields up 82 %. Part 2 The second part consisted on the development of a fluorescence probe using a fla-vylium ion for in vivo imaging. In order to develop a fluorescent system that could be used in in vivo imaging for detection cancer cells, the prepared flavilyum was coupled with the theraupeutical relevant Celastrol. A new flavilyum ion was synthesized via condensation of a 7-diethylaminophenol with acetophenone possessing an halogenated alkylic linker at the 4’ position. Different pathways were investigated in order to reach and optimize the synthesis of a C4 functionalized flavylium salt that was prepared in three steps. Attempts were performed to couple the prepared flavylium to Celastrol. |
publishDate |
2017 |
dc.date.none.fl_str_mv |
2017-11 2017-11 2017-11-01T00:00:00Z 2021-01-21T01:30:18Z |
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.uri.fl_str_mv |
http://hdl.handle.net/10362/25873 |
url |
http://hdl.handle.net/10362/25873 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
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.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
repository.mail.fl_str_mv |
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1799137909710782464 |