Síntese, Caracterização e Avaliação Biológica de Aril- Sidnonas e Novos Híbridos Sulfonamidas-Sidnonas

Detalhes bibliográficos
Autor(a) principal: Barbosa, Igor Resendes
Data de Publicação: 2021
Tipo de documento: Dissertação
Idioma: por
Título da fonte: Repositório Institucional da UFRRJ
Texto Completo: https://rima.ufrrj.br/jspui/handle/20.500.14407/17684
Resumo: As leishmanioses são um conjunto de doenças causadas por parasitos do gênero Leishamania. São endêmicas em cerca de 98 países e territórios e classificadas pela OMS como Doenças Tropicais Negligenciadas. Afetam milhares de pessoas todo ano, causando alta mortalidade e morbidade. Os tratamentos dessas parasitoses são baseados em quimioterapia, contando com um número reduzido de fármacos disponíveis, os quais apresentam diversas limitações, como alto custo, forma de administração inconvenientes e muitas vezes dolorosas e efeitos colaterais adversos graves. Além disso, o desenvolvimento de resistência clínica tem se tornado um problema emergente, tendo sido registrados casos para todas as substâncias anti leishmania de uso clínico. Tendo em vista o gravíssimo cenário criado pelas leishmanioses e o interesse do nosso grupo de pesquisa nos compostos mesoiônicos e suas atividades biológicas, esse trabalho de dissertação apresenta o planejamento e a obtenção de duas séries de sidnonas com potenciais atividades leishmanicidas: a primeira, composta por 13 N-aril-sidnonas e N alquil-sidnonas simples (já relatadas na literatura) e a segunda, formada por 8 híbridos sulfonamidas-sidnonas inéditos. A primeira série de sidnonas foi preparada em três etapas, por meio da rota sintética clássica amplamente descrita na literatura. Os híbridos, por sua vez, foram obtidos por duas etapas adicionais, partindo da N-(4-nitro-fenil)-sidnona ou da N-(3- nitro-fenil)-sidnona. Para isso, o grupo nitro desses compostos foi inicialmente reduzido a amino, com uso de cloreto estanhoso, rendendo as N-(amino-fenil)-sidnonas. Por fim, as sulfonamidas-sidnonas foram obtidas por maceração entre as respectivas N-(amino-fenil)- sidnonas e os cloretos de sulfonila adequados, na presença de carbonato de sódio e sílica gel. Os produtos obtidos foram caracterizados por espectroscopia no infravermelho, RMN de 1H e 13C. No caso dos compostos inéditos foram realizados experimentos bidimensionais de RMN (COSY, NOESY, HSQC e HMBC) para a atribuição correta de todos os sinais observados nos espectros 1D de 1H e 13C. Este trabalho propõe uma rota viável para o preparo de sulfonamidas-sidnonas e apresenta uma discussão detalhada no que se refere a determinação estrutural desses compostos e de seus intermediários sintéticos. Todas as treze sidnonas da primeira série foram avaliadas in vitro frente à forma promastigota da L.amazonensis. Dessas, somente a fenil-sidnona não substituída e aquelas contendo um grupo nitro no anel benzênico apresentaram IC50 abaixo da maior concentração avaliada (<128 µM). A N-(3-nitro-fenil)- sidnona foi o composto mais potente, com IC50 de 18,22 µM
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spelling Barbosa, Igor ResendesLima, Aurea Echevarria Aznar Neveshttp://lattes.cnpq.br/1879077396134052Lima, Aurea Echevarria Aznar Neveshttp://lattes.cnpq.br/1879077396134052Pinheiro, Luiz Carlos da Silvahttps://orcid.org/0000-0002-6398-7717http://lattes.cnpq.br/5040259412514046Santos, Cláudio Eduardo Rodrigues doshttps://orcid.org/0000-0003-0129-2802http://lattes.cnpq.br/0890271430013129Castro, Rosane Norahttps://orcid.org/0000-0001-8983-3786http://lattes.cnpq.br/5479814788308057Marra, Roberta Katlen Fuscohttp://lattes.cnpq.br/0899105923944274http://lattes.cnpq.br/34293350810890672024-08-08T17:01:12Z2024-08-08T17:01:12Z2021-01-26ARBOSA, Igor Resendes. Síntese, Caracterização e Avaliação Biológica de Aril Sidnonas e Novos Híbridos Sulfonamidas-Sidnonas, 2021, 156 f. Dissertação (Mestrado em Química) - Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica, 2021.https://rima.ufrrj.br/jspui/handle/20.500.14407/17684As leishmanioses são um conjunto de doenças causadas por parasitos do gênero Leishamania. São endêmicas em cerca de 98 países e territórios e classificadas pela OMS como Doenças Tropicais Negligenciadas. Afetam milhares de pessoas todo ano, causando alta mortalidade e morbidade. Os tratamentos dessas parasitoses são baseados em quimioterapia, contando com um número reduzido de fármacos disponíveis, os quais apresentam diversas limitações, como alto custo, forma de administração inconvenientes e muitas vezes dolorosas e efeitos colaterais adversos graves. Além disso, o desenvolvimento de resistência clínica tem se tornado um problema emergente, tendo sido registrados casos para todas as substâncias anti leishmania de uso clínico. Tendo em vista o gravíssimo cenário criado pelas leishmanioses e o interesse do nosso grupo de pesquisa nos compostos mesoiônicos e suas atividades biológicas, esse trabalho de dissertação apresenta o planejamento e a obtenção de duas séries de sidnonas com potenciais atividades leishmanicidas: a primeira, composta por 13 N-aril-sidnonas e N alquil-sidnonas simples (já relatadas na literatura) e a segunda, formada por 8 híbridos sulfonamidas-sidnonas inéditos. A primeira série de sidnonas foi preparada em três etapas, por meio da rota sintética clássica amplamente descrita na literatura. Os híbridos, por sua vez, foram obtidos por duas etapas adicionais, partindo da N-(4-nitro-fenil)-sidnona ou da N-(3- nitro-fenil)-sidnona. Para isso, o grupo nitro desses compostos foi inicialmente reduzido a amino, com uso de cloreto estanhoso, rendendo as N-(amino-fenil)-sidnonas. Por fim, as sulfonamidas-sidnonas foram obtidas por maceração entre as respectivas N-(amino-fenil)- sidnonas e os cloretos de sulfonila adequados, na presença de carbonato de sódio e sílica gel. Os produtos obtidos foram caracterizados por espectroscopia no infravermelho, RMN de 1H e 13C. No caso dos compostos inéditos foram realizados experimentos bidimensionais de RMN (COSY, NOESY, HSQC e HMBC) para a atribuição correta de todos os sinais observados nos espectros 1D de 1H e 13C. Este trabalho propõe uma rota viável para o preparo de sulfonamidas-sidnonas e apresenta uma discussão detalhada no que se refere a determinação estrutural desses compostos e de seus intermediários sintéticos. Todas as treze sidnonas da primeira série foram avaliadas in vitro frente à forma promastigota da L.amazonensis. Dessas, somente a fenil-sidnona não substituída e aquelas contendo um grupo nitro no anel benzênico apresentaram IC50 abaixo da maior concentração avaliada (<128 µM). A N-(3-nitro-fenil)- sidnona foi o composto mais potente, com IC50 de 18,22 µMConselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqCoordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESFundação de Amparo à Pesquisa do Estado do Rio de Janeiro - FAPERJLeishmaniasis are a group of diseases caused by parasites from the genus Leishmania. They are endemic in about 98 countries and territories and classified by WHO as Neglected Tropical Diseases. They affect thousands of people every year, causing high mortality and morbidity. Treatments for these parasitic infections are based on chemotherapy, with a small number of available drugs, which have several limitations, such as high costs, inconvenient and often painful route of administration and serious adverse effects. In addition the surge of resistance has become an emerging problem, with reported cases for all anti-leishmania substances of clinical use. In view of the very serious scenario created by leishmaniasis and the interest of our research group in mesoionic compounds and their biological activities, this dissertation presents the design and preparation of two series of sydnones with potential leishmanicidal activities: the first, composed of 13 simple N-aryl-sydnones and N-alkyl sydnones (wich have already been reported in the literature), and the second, consisting of 8 novel sulfonamide sidnona hybrids. The first series of Sydnones was prepared in three steps, using the classic synthetic route widely described in the literature. The hybrids, in turn, were obtained by two additional steps, starting from the N-(4-nitro-phenyl)-sydnone or N-(3-nitro phenyl)-sydnone. For this, the nitro group of these compounds was initially reduced using stannous chloride, yielding the N-(amino-phenyl)-sydnones. Finally, the sulfonamide-sydnone hybrids were obtained by maceration between the respective N-(amino-phenyl)-sydnones and the appropriate sulfonyl chlorides, in the presence of sodium carbonate and silica gel. The products were characterized by infrared spectroscopy, 1H and 13C NMR. In the case of the novel compounds, two-dimensional NMR experiments (COSY, NOESY, HSQC, HMBC) were also performed to correctly assign all signals observed in the 1D 1H and 13C spectra. This work proposes a viable rout for the preparation of sulfonamide-sydnones and presents a detailed discussion regarding the structural determination of these compounds and their synthetic intermediates. All thirteen sydnones from the first series were evaluated in vitro against the promastigote form of L. amasonensis. Of these, only the unsubstituted phenyl sydnone and those containing a nitro group in the benzene ring showed IC50 values below the highest concentration tested (< 128 µM). 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dc.title.pt_BR.fl_str_mv Síntese, Caracterização e Avaliação Biológica de Aril- Sidnonas e Novos Híbridos Sulfonamidas-Sidnonas
dc.title.alternative.en.fl_str_mv Synthesis, Characterization and Biological Evaluation of Aryl-Sydnones and New Sulfonamide-Sydnone Hybrids
title Síntese, Caracterização e Avaliação Biológica de Aril- Sidnonas e Novos Híbridos Sulfonamidas-Sidnonas
spellingShingle Síntese, Caracterização e Avaliação Biológica de Aril- Sidnonas e Novos Híbridos Sulfonamidas-Sidnonas
Barbosa, Igor Resendes
Química
sidnonas
sulfonamidas
mesoiônicos
sydnones
sulfonamides
mesoionic
title_short Síntese, Caracterização e Avaliação Biológica de Aril- Sidnonas e Novos Híbridos Sulfonamidas-Sidnonas
title_full Síntese, Caracterização e Avaliação Biológica de Aril- Sidnonas e Novos Híbridos Sulfonamidas-Sidnonas
title_fullStr Síntese, Caracterização e Avaliação Biológica de Aril- Sidnonas e Novos Híbridos Sulfonamidas-Sidnonas
title_full_unstemmed Síntese, Caracterização e Avaliação Biológica de Aril- Sidnonas e Novos Híbridos Sulfonamidas-Sidnonas
title_sort Síntese, Caracterização e Avaliação Biológica de Aril- Sidnonas e Novos Híbridos Sulfonamidas-Sidnonas
author Barbosa, Igor Resendes
author_facet Barbosa, Igor Resendes
author_role author
dc.contributor.author.fl_str_mv Barbosa, Igor Resendes
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 Lima, Aurea Echevarria Aznar Neves
dc.contributor.referee1Lattes.fl_str_mv http://lattes.cnpq.br/1879077396134052
dc.contributor.referee2.fl_str_mv Pinheiro, Luiz Carlos da Silva
dc.contributor.referee2ID.fl_str_mv https://orcid.org/0000-0002-6398-7717
dc.contributor.referee2Lattes.fl_str_mv http://lattes.cnpq.br/5040259412514046
dc.contributor.referee3.fl_str_mv Santos, Cláudio Eduardo Rodrigues dos
dc.contributor.referee3ID.fl_str_mv https://orcid.org/0000-0003-0129-2802
dc.contributor.referee3Lattes.fl_str_mv http://lattes.cnpq.br/0890271430013129
dc.contributor.referee4.fl_str_mv Castro, Rosane Nora
dc.contributor.referee4ID.fl_str_mv https://orcid.org/0000-0001-8983-3786
dc.contributor.referee4Lattes.fl_str_mv http://lattes.cnpq.br/5479814788308057
dc.contributor.referee5.fl_str_mv Marra, Roberta Katlen Fusco
dc.contributor.referee5Lattes.fl_str_mv http://lattes.cnpq.br/0899105923944274
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/3429335081089067
contributor_str_mv Lima, Aurea Echevarria Aznar Neves
Lima, Aurea Echevarria Aznar Neves
Pinheiro, Luiz Carlos da Silva
Santos, Cláudio Eduardo Rodrigues dos
Castro, Rosane Nora
Marra, Roberta Katlen Fusco
dc.subject.cnpq.fl_str_mv Química
topic Química
sidnonas
sulfonamidas
mesoiônicos
sydnones
sulfonamides
mesoionic
dc.subject.por.fl_str_mv sidnonas
sulfonamidas
mesoiônicos
sydnones
sulfonamides
mesoionic
description As leishmanioses são um conjunto de doenças causadas por parasitos do gênero Leishamania. São endêmicas em cerca de 98 países e territórios e classificadas pela OMS como Doenças Tropicais Negligenciadas. Afetam milhares de pessoas todo ano, causando alta mortalidade e morbidade. Os tratamentos dessas parasitoses são baseados em quimioterapia, contando com um número reduzido de fármacos disponíveis, os quais apresentam diversas limitações, como alto custo, forma de administração inconvenientes e muitas vezes dolorosas e efeitos colaterais adversos graves. Além disso, o desenvolvimento de resistência clínica tem se tornado um problema emergente, tendo sido registrados casos para todas as substâncias anti leishmania de uso clínico. Tendo em vista o gravíssimo cenário criado pelas leishmanioses e o interesse do nosso grupo de pesquisa nos compostos mesoiônicos e suas atividades biológicas, esse trabalho de dissertação apresenta o planejamento e a obtenção de duas séries de sidnonas com potenciais atividades leishmanicidas: a primeira, composta por 13 N-aril-sidnonas e N alquil-sidnonas simples (já relatadas na literatura) e a segunda, formada por 8 híbridos sulfonamidas-sidnonas inéditos. A primeira série de sidnonas foi preparada em três etapas, por meio da rota sintética clássica amplamente descrita na literatura. Os híbridos, por sua vez, foram obtidos por duas etapas adicionais, partindo da N-(4-nitro-fenil)-sidnona ou da N-(3- nitro-fenil)-sidnona. Para isso, o grupo nitro desses compostos foi inicialmente reduzido a amino, com uso de cloreto estanhoso, rendendo as N-(amino-fenil)-sidnonas. Por fim, as sulfonamidas-sidnonas foram obtidas por maceração entre as respectivas N-(amino-fenil)- sidnonas e os cloretos de sulfonila adequados, na presença de carbonato de sódio e sílica gel. Os produtos obtidos foram caracterizados por espectroscopia no infravermelho, RMN de 1H e 13C. No caso dos compostos inéditos foram realizados experimentos bidimensionais de RMN (COSY, NOESY, HSQC e HMBC) para a atribuição correta de todos os sinais observados nos espectros 1D de 1H e 13C. Este trabalho propõe uma rota viável para o preparo de sulfonamidas-sidnonas e apresenta uma discussão detalhada no que se refere a determinação estrutural desses compostos e de seus intermediários sintéticos. Todas as treze sidnonas da primeira série foram avaliadas in vitro frente à forma promastigota da L.amazonensis. Dessas, somente a fenil-sidnona não substituída e aquelas contendo um grupo nitro no anel benzênico apresentaram IC50 abaixo da maior concentração avaliada (<128 µM). A N-(3-nitro-fenil)- sidnona foi o composto mais potente, com IC50 de 18,22 µM
publishDate 2021
dc.date.issued.fl_str_mv 2021-01-26
dc.date.accessioned.fl_str_mv 2024-08-08T17:01:12Z
dc.date.available.fl_str_mv 2024-08-08T17:01:12Z
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 ARBOSA, Igor Resendes. Síntese, Caracterização e Avaliação Biológica de Aril Sidnonas e Novos Híbridos Sulfonamidas-Sidnonas, 2021, 156 f. Dissertação (Mestrado em Química) - Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica, 2021.
dc.identifier.uri.fl_str_mv https://rima.ufrrj.br/jspui/handle/20.500.14407/17684
identifier_str_mv ARBOSA, Igor Resendes. Síntese, Caracterização e Avaliação Biológica de Aril Sidnonas e Novos Híbridos Sulfonamidas-Sidnonas, 2021, 156 f. Dissertação (Mestrado em Química) - Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica, 2021.
url https://rima.ufrrj.br/jspui/handle/20.500.14407/17684
dc.language.iso.fl_str_mv por
language por
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