Mesoi?nicos 1,3,4-tiadiaz?lio-2-aminidas: s?ntese, solvatocromismo & citotoxidade

Detalhes bibliográficos
Autor(a) principal: Silva, Edson Fernandes da
Data de Publicação: 1998
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/4189
Resumo: Mesoionic compounds are heterocycles with dipolar structure. They have considered interesting because of their diversificating biological activity and other applications like new materiais and colourings. Four news mesoionic compounds of 1,3,4-thiadiazolium-2-aminide class, with p-substituted cinnamoyl group and seven chloridrates of the same class were synthesized. The methodology of the synthesis consisted in the anhidroacylation reaction of thiossemicarbazides with p-substituted cinnamoyl acid chlorides, after that a tratment with base was used. This compounds were characterized by espectroscopic technics, specially NMR 1H and 13C and ultraviolet. The pKa (s) values were determined with spectrophotometric method. A mild acid nature and significant correlationship with dual parameters of substituents, sR, were observed. The solvatochromic properties ofthe synthesized compounds were investigated. New empiric scales of polarity were stablished by a transition energy change in ultraviolet spectro. The ET (BLD) and ET (MIH) scales were correlated with other empiric scales of polarity, where ET (30), ET (26), Z, S, X R, XB and Py were the best correlations showed. Quimiosensibility assays against Ehrlich carcinoma's cells showed significant citotoxic activity for mesoionic compounds and their salts
id UFRRJ-1_4b84cfa49c34549479a3a32633f05c11
oai_identifier_str oai:localhost:jspui/4189
network_acronym_str UFRRJ-1
network_name_str Biblioteca Digital de Teses e Dissertações da UFRRJ
repository_id_str
spelling Lima, Aurea Echevarria Aznar Neveshttp://lattes.cnpq.br/1879077396134052Freitas, Antonio Carlos Carreira deLima, Aurea Echevarria Aznar NevesLima, Marco Edilson Freire deLeon, Leonor Laurahttp://lattes.cnpq.br/3069352193177705Silva, Edson Fernandes da2020-11-24T16:13:50Z1998-01-12SILVA, Edson Fernandes da. Mesoi?nicos 1,3,4-tiadiaz?lio-2-aminidas: s?ntese, solvatocromismo & citotoxidade. 1998. 171 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 1998.https://tede.ufrrj.br/jspui/handle/jspui/4189Mesoionic compounds are heterocycles with dipolar structure. They have considered interesting because of their diversificating biological activity and other applications like new materiais and colourings. Four news mesoionic compounds of 1,3,4-thiadiazolium-2-aminide class, with p-substituted cinnamoyl group and seven chloridrates of the same class were synthesized. The methodology of the synthesis consisted in the anhidroacylation reaction of thiossemicarbazides with p-substituted cinnamoyl acid chlorides, after that a tratment with base was used. This compounds were characterized by espectroscopic technics, specially NMR 1H and 13C and ultraviolet. The pKa (s) values were determined with spectrophotometric method. A mild acid nature and significant correlationship with dual parameters of substituents, sR, were observed. The solvatochromic properties ofthe synthesized compounds were investigated. New empiric scales of polarity were stablished by a transition energy change in ultraviolet spectro. The ET (BLD) and ET (MIH) scales were correlated with other empiric scales of polarity, where ET (30), ET (26), Z, S, X R, XB and Py were the best correlations showed. Quimiosensibility assays against Ehrlich carcinoma's cells showed significant citotoxic activity for mesoionic compounds and their saltsOs compostos mesi?nicos s?o heterociclos com estrutura dipolar. Esses compostos tem apresentado bastante interesse devido ? sua diversificada atividade biol?gica, e tamb?m devido a sua utiliza??o como novos materiais e corantes, entre outras. Sintetizamos 4 novos mesoi?nicos da classe 1,3,4-tiadiaz?lio-2- aminida, contendo um grupamento cinamo?la p-substitu?do, e 7 cloridratos precursores desta mesma classe. A metodologia utilizada envolveu a rea??o de acila??o anidra de tiossemicarbazidas na presen?a de cloretos de ?cido cinamoilsubstitu?dos e posterior tratamento com base. Esses compostos foram caracterizados por t?cnicas espectrosc?picas, principalmente RMN de 1H e 13C e ultra-violeta. Foram determinados, atrav?s de m?todo espectrofotom?trico os valores de pKa (s) dos cloridratos dos mesoi?nicos, indicando natureza moderadamente ?cida, apresentando correla??o significativa com os par?metros duais dos substituintes, sR. As propriedades solvatocr?micas dos compostos sintetizados foram investigadas e, estabeleceu-se novas escalas emp?ricas de polaridade utilizando a varia??o da energia de transi??o entre o estado fundamental e excitado na regi?o do ultra-violeta. As escalas E T (BLD) e ET (MIH) foram correlacionadas com outras escalas emp?ricas de polaridade, apresentando melhores correla??es para E T (30), ET (26), Z, S, XR, XB e Py. Ensaios de quimiosensibilidade frente a c?lulas do carcinoma de Ehrlich foram realizados, indicando significativa atividade citot?xica para os mesoi?nicos e seus respectivos sais.Submitted by Celso Magalhaes (celsomagalhaes@ufrrj.br) on 2020-11-24T16:13:50Z No. of bitstreams: 1 1997 - Edson Fernandes da Silva.pdf: 8144640 bytes, checksum: eb008a4021b35da58b8752e5abbd9f1a (MD5)Made available in DSpace on 2020-11-24T16:13:50Z (GMT). No. of bitstreams: 1 1997 - Edson Fernandes da Silva.pdf: 8144640 bytes, checksum: eb008a4021b35da58b8752e5abbd9f1a (MD5) Previous issue date: 1998-01-12Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior - CAPESapplication/pdfhttps://tede.ufrrj.br/retrieve/63174/1997%20-%20Edson%20Fernandes%20da%20Silva.pdf.jpgporUniversidade Federal Rural do Rio de JaneiroPrograma de P?s-Gradua??o em Qu?micaUFRRJBrasilInstituto de Ci?ncias Exatasqu?mica org?nicacompostos mesi?nicosQu?micaMesoi?nicos 1,3,4-tiadiaz?lio-2-aminidas: s?ntese, solvatocromismo & citotoxidadeinfo: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:UFRRJTHUMBNAIL1997 - Edson Fernandes da Silva.pdf.jpg1997 - Edson Fernandes da Silva.pdf.jpgimage/jpeg2961http://localhost:8080/tede/bitstream/jspui/4189/4/1997+-+Edson+Fernandes+da+Silva.pdf.jpgf642c2332cea0c1bc678089e12da06c5MD54TEXT1997 - Edson Fernandes da Silva.pdf.txt1997 - Edson Fernandes da Silva.pdf.txttext/plain60793http://localhost:8080/tede/bitstream/jspui/4189/3/1997+-+Edson+Fernandes+da+Silva.pdf.txtef8b8382430a4383b206e69e99025060MD53ORIGINAL1997 - Edson Fernandes da Silva.pdf1997 - Edson Fernandes da Silva.pdfapplication/pdf8144640http://localhost:8080/tede/bitstream/jspui/4189/2/1997+-+Edson+Fernandes+da+Silva.pdfeb008a4021b35da58b8752e5abbd9f1aMD52LICENSElicense.txtlicense.txttext/plain; charset=utf-82089http://localhost:8080/tede/bitstream/jspui/4189/1/license.txt7b5ba3d2445355f386edab96125d42b7MD51jspui/41892021-06-08 10:29:02.244oai: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:2021-06-08T13:29:02Biblioteca Digital de Teses e Dissertações da UFRRJ - Universidade Federal Rural do Rio de Janeiro (UFRRJ)false
dc.title.por.fl_str_mv Mesoi?nicos 1,3,4-tiadiaz?lio-2-aminidas: s?ntese, solvatocromismo & citotoxidade
title Mesoi?nicos 1,3,4-tiadiaz?lio-2-aminidas: s?ntese, solvatocromismo & citotoxidade
spellingShingle Mesoi?nicos 1,3,4-tiadiaz?lio-2-aminidas: s?ntese, solvatocromismo & citotoxidade
Silva, Edson Fernandes da
qu?mica org?nica
compostos mesi?nicos
Qu?mica
title_short Mesoi?nicos 1,3,4-tiadiaz?lio-2-aminidas: s?ntese, solvatocromismo & citotoxidade
title_full Mesoi?nicos 1,3,4-tiadiaz?lio-2-aminidas: s?ntese, solvatocromismo & citotoxidade
title_fullStr Mesoi?nicos 1,3,4-tiadiaz?lio-2-aminidas: s?ntese, solvatocromismo & citotoxidade
title_full_unstemmed Mesoi?nicos 1,3,4-tiadiaz?lio-2-aminidas: s?ntese, solvatocromismo & citotoxidade
title_sort Mesoi?nicos 1,3,4-tiadiaz?lio-2-aminidas: s?ntese, solvatocromismo & citotoxidade
author Silva, Edson Fernandes da
author_facet Silva, Edson Fernandes da
author_role author
dc.contributor.advisor1.fl_str_mv Lima, Aurea Echevarria Aznar Neves
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/1879077396134052
dc.contributor.referee1.fl_str_mv Freitas, Antonio Carlos Carreira de
dc.contributor.referee2.fl_str_mv Lima, Aurea Echevarria Aznar Neves
dc.contributor.referee3.fl_str_mv Lima, Marco Edilson Freire de
dc.contributor.referee4.fl_str_mv Leon, Leonor Laura
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/3069352193177705
dc.contributor.author.fl_str_mv Silva, Edson Fernandes da
contributor_str_mv Lima, Aurea Echevarria Aznar Neves
Freitas, Antonio Carlos Carreira de
Lima, Aurea Echevarria Aznar Neves
Lima, Marco Edilson Freire de
Leon, Leonor Laura
dc.subject.por.fl_str_mv qu?mica org?nica
compostos mesi?nicos
topic qu?mica org?nica
compostos mesi?nicos
Qu?mica
dc.subject.cnpq.fl_str_mv Qu?mica
description Mesoionic compounds are heterocycles with dipolar structure. They have considered interesting because of their diversificating biological activity and other applications like new materiais and colourings. Four news mesoionic compounds of 1,3,4-thiadiazolium-2-aminide class, with p-substituted cinnamoyl group and seven chloridrates of the same class were synthesized. The methodology of the synthesis consisted in the anhidroacylation reaction of thiossemicarbazides with p-substituted cinnamoyl acid chlorides, after that a tratment with base was used. This compounds were characterized by espectroscopic technics, specially NMR 1H and 13C and ultraviolet. The pKa (s) values were determined with spectrophotometric method. A mild acid nature and significant correlationship with dual parameters of substituents, sR, were observed. The solvatochromic properties ofthe synthesized compounds were investigated. New empiric scales of polarity were stablished by a transition energy change in ultraviolet spectro. The ET (BLD) and ET (MIH) scales were correlated with other empiric scales of polarity, where ET (30), ET (26), Z, S, X R, XB and Py were the best correlations showed. Quimiosensibility assays against Ehrlich carcinoma's cells showed significant citotoxic activity for mesoionic compounds and their salts
publishDate 1998
dc.date.issued.fl_str_mv 1998-01-12
dc.date.accessioned.fl_str_mv 2020-11-24T16:13:50Z
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 SILVA, Edson Fernandes da. Mesoi?nicos 1,3,4-tiadiaz?lio-2-aminidas: s?ntese, solvatocromismo & citotoxidade. 1998. 171 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 1998.
dc.identifier.uri.fl_str_mv https://tede.ufrrj.br/jspui/handle/jspui/4189
identifier_str_mv SILVA, Edson Fernandes da. Mesoi?nicos 1,3,4-tiadiaz?lio-2-aminidas: s?ntese, solvatocromismo & citotoxidade. 1998. 171 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 1998.
url https://tede.ufrrj.br/jspui/handle/jspui/4189
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 reponame:Biblioteca Digital de Teses e Dissertações da UFRRJ
instname:Universidade Federal Rural do Rio de Janeiro (UFRRJ)
instacron:UFRRJ
instname_str Universidade Federal Rural do Rio de Janeiro (UFRRJ)
instacron_str UFRRJ
institution UFRRJ
reponame_str Biblioteca Digital de Teses e Dissertações da UFRRJ
collection Biblioteca Digital de Teses e Dissertações da UFRRJ
bitstream.url.fl_str_mv http://localhost:8080/tede/bitstream/jspui/4189/4/1997+-+Edson+Fernandes+da+Silva.pdf.jpg
http://localhost:8080/tede/bitstream/jspui/4189/3/1997+-+Edson+Fernandes+da+Silva.pdf.txt
http://localhost:8080/tede/bitstream/jspui/4189/2/1997+-+Edson+Fernandes+da+Silva.pdf
http://localhost:8080/tede/bitstream/jspui/4189/1/license.txt
bitstream.checksum.fl_str_mv f642c2332cea0c1bc678089e12da06c5
ef8b8382430a4383b206e69e99025060
eb008a4021b35da58b8752e5abbd9f1a
7b5ba3d2445355f386edab96125d42b7
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
MD5
MD5
repository.name.fl_str_mv Biblioteca Digital de Teses e Dissertações da UFRRJ - Universidade Federal Rural do Rio de Janeiro (UFRRJ)
repository.mail.fl_str_mv bibliot@ufrrj.br||bibliot@ufrrj.br
_version_ 1800313516878462976

Registros relacionados