Síntese de derivados benzofenônicos com potencial antifúngico e anti-leishmania

Detalhes bibliográficos
Ano de defesa: 2012
Autor(a) principal: Maciel-Rezende, Claudia Mara lattes
Orientador(a): Santos, Marcelo Henrique Dos lattes
Banca de defesa: Dias, Amanda Latercia Tranches, Ramalho, Teodorico De Castro
Tipo de documento: Dissertação
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal de Alfenas
Programa de Pós-Graduação: Programa de Pós-Graduação em Química
Departamento: Instituto de Química
País: Brasil
Palavras-chave em Português:
Área do conhecimento CNPq:
Link de acesso: https://repositorio.unifal-mg.edu.br/handle/123456789/359
Resumo: The benzophenones are used largely as synthetic intermediary in the chemical and pharmaceutical industry. They are objective of continuous investigations of biological interest due to properties, such as: insecticide, anti-aggregation platelet, inhibitory of xanthine oxidase, antioxidant, anti-microbial, anti-inflammatory and anti-proliferative. In this work it is described the synthesis of the methyl, butyl and prenyl derivatives of the benzofenones 2,4-di-hydroxybenzofenone, 4-hydroxybenzofenone and 4,4'-di-hydroxybenzofenone, following by the characterization for techniques spectroscopic and spectrometric (infrared, ultraviolet-visible and nuclear magnetic resonance and mass spectrometry). The compounds were submitted to the tests of antioxidant activity for the mechanism of scavenging of free radicals DPPH, inhibitory of xanthine oxidase and anti-microbial (bacteria, fungi and Leishmania) in order to link the chemical structure with the biological activity of the analyzed compositions. Flowed tested they didn't present significant results for the antioxidant activity in relation to the ascorbic acid pattern, once the substitutions increased the lipophilic character of the molecules in relation to the ascorbic acid pattern. In the test of inhibition of xanthine oxidase, flowed obtained they were not appraised due to yours no solubility in the middle. For the anti-bacterial (Gram-positive and Gram-negatives) activity, derived them didn't also present inhibitory activity in the tested microorganisms. In the activity anti-fungal, the butyl derivative was more active than the fluconazole. In the activity leishmanicida (promastigote form), the methyl and prenyl derivatives presented significant inhibitory activity when compared to amphotericin-B. The obtained results evidenced that the variation of the lipophilicity of the molecules is an important point for the biological activity and that some structural modifications accomplished in the benzofenonas took her flowed more potent, selective and little toxic against different types of microorganisms pathogenic.
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spelling Maciel-Rezende, Claudia Marahttp://lattes.cnpq.br/4558270749970982Viegas Junior, CláudioDias, Amanda Latercia TranchesRamalho, Teodorico De CastroSantos, Marcelo Henrique Doshttp://lattes.cnpq.br/79027558661461612015-06-10T00:18:16Z2012-02-29MACIEL-REZENDE, Claudia Mara. Síntese de derivados benzofenônicos com potencial antifúngico e anti-leishmania. 2012. 138 f. Dissertação (Mestrado em Química) - Universidade Federal de Alfenas, Alfenas, MG, 2012.https://repositorio.unifal-mg.edu.br/handle/123456789/359The benzophenones are used largely as synthetic intermediary in the chemical and pharmaceutical industry. They are objective of continuous investigations of biological interest due to properties, such as: insecticide, anti-aggregation platelet, inhibitory of xanthine oxidase, antioxidant, anti-microbial, anti-inflammatory and anti-proliferative. In this work it is described the synthesis of the methyl, butyl and prenyl derivatives of the benzofenones 2,4-di-hydroxybenzofenone, 4-hydroxybenzofenone and 4,4'-di-hydroxybenzofenone, following by the characterization for techniques spectroscopic and spectrometric (infrared, ultraviolet-visible and nuclear magnetic resonance and mass spectrometry). The compounds were submitted to the tests of antioxidant activity for the mechanism of scavenging of free radicals DPPH, inhibitory of xanthine oxidase and anti-microbial (bacteria, fungi and Leishmania) in order to link the chemical structure with the biological activity of the analyzed compositions. Flowed tested they didn't present significant results for the antioxidant activity in relation to the ascorbic acid pattern, once the substitutions increased the lipophilic character of the molecules in relation to the ascorbic acid pattern. In the test of inhibition of xanthine oxidase, flowed obtained they were not appraised due to yours no solubility in the middle. For the anti-bacterial (Gram-positive and Gram-negatives) activity, derived them didn't also present inhibitory activity in the tested microorganisms. In the activity anti-fungal, the butyl derivative was more active than the fluconazole. In the activity leishmanicida (promastigote form), the methyl and prenyl derivatives presented significant inhibitory activity when compared to amphotericin-B. The obtained results evidenced that the variation of the lipophilicity of the molecules is an important point for the biological activity and that some structural modifications accomplished in the benzofenonas took her flowed more potent, selective and little toxic against different types of microorganisms pathogenic.As benzofenonas são amplamente utilizadas como intermediários sintéticos na indústria química e farmacêutica. Elas são alvo de contínuas investigações de interesse biológico devido a propriedades, tais como: inseticida, anti-agregação plaquetária, inibitória de xantine oxidase, antioxidante, antimicrobiano, anti-inflamatório e anti-proliferativo. Neste trabalho é descrita a síntese dos derivados metilados, butilados e prenilados das benzofenonas 2,4-diidroxibenzofenona, 4-hidroxibenzofenona e 4,4’-diidroxibenzofenona, seguido da caracterização por técnicas espectroscopicas e espectrométricas (infravermelho, ultravioleta-visível e ressonância magnética nuclear,e espectrometria de massas). Os derivados foram submetidos aos testes de atividade antioxidante pelo mecanismo de captação de radicais livres DPPH, inibitória de xantina oxidase e antimicrobiana (bactérias, fungos e leishmania) a fim de se relacionar a estrutura química com a atividade biológica dos compostos analisados. Os derivados testados não apresentaram resultados significantes para a atividade antioxidante em relação ao padrão ácido ascórbico, uma vez que as substituições aumentaram o caráter lipofílico das moléculas em relação ao padrão ácido ascórbico. No teste de inibição de xantina oxidase, os derivados obtidos não foram avaliados devido a sua não solubilidade no meio. Para a atividade antibacteriana (Gram-positivas e Gram-negativas), os derivados também não apresentaram atividade inibitória nos microrganismos testados. Na atividade antifúngica, o derivado butilado foi mais ativo do que o fluconazol. Na atividade leishmanicida (forma promastigota), os derivados metilados e prenilados apresentaram atividade inibitória significativa quando comparados à Anfotericina-B. Os resultados obtidos evidenciaram que a variação da lipofilicidade da molécula é um ponto importante para a atividade biológica e que algumas modificações estruturais realizadas nas benzofenonas levaram a derivados mais potentes, seletivos e pouco tóxicos contra diferentes tipos de microrganismos patogênicos.application/pdfporUniversidade Federal de AlfenasPrograma de Pós-Graduação em QuímicaUNIFAL-MGBrasilInstituto de Químicainfo:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-nd/4.0/BenzofenonasBacteriasFungosLeishmaniaQUIMICA::QUIMICA ORGANICASíntese de derivados benzofenônicos com potencial antifúngico e anti-leishmaniainfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/publishedVersion1328253078826782306600600-8194069717282802154reponame:Repositório Institucional da Universidade Federal de Alfenas - RiUnifalinstname:Universidade Federal de Alfenas (UNIFAL)instacron:UNIFALMaciel-Rezende, Claudia MaraLICENSElicense.txtlicense.txttext/plain; charset=utf-81987https://repositorio.unifal-mg.edu.br/bitstreams/8f4a44c4-5116-4d2e-9979-3b6664565ef2/download31555718c4fc75849dd08f27935d4f6bMD51CC-LICENSElicense_urllicense_urltext/plain; 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dc.title.pt-BR.fl_str_mv Síntese de derivados benzofenônicos com potencial antifúngico e anti-leishmania
title Síntese de derivados benzofenônicos com potencial antifúngico e anti-leishmania
spellingShingle Síntese de derivados benzofenônicos com potencial antifúngico e anti-leishmania
Maciel-Rezende, Claudia Mara
Benzofenonas
Bacterias
Fungos
Leishmania
QUIMICA::QUIMICA ORGANICA
title_short Síntese de derivados benzofenônicos com potencial antifúngico e anti-leishmania
title_full Síntese de derivados benzofenônicos com potencial antifúngico e anti-leishmania
title_fullStr Síntese de derivados benzofenônicos com potencial antifúngico e anti-leishmania
title_full_unstemmed Síntese de derivados benzofenônicos com potencial antifúngico e anti-leishmania
title_sort Síntese de derivados benzofenônicos com potencial antifúngico e anti-leishmania
author Maciel-Rezende, Claudia Mara
author_facet Maciel-Rezende, Claudia Mara
author_role author
dc.contributor.author.fl_str_mv Maciel-Rezende, Claudia Mara
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/4558270749970982
dc.contributor.advisor-co1.fl_str_mv Viegas Junior, Cláudio
dc.contributor.referee1.fl_str_mv Dias, Amanda Latercia Tranches
dc.contributor.referee2.fl_str_mv Ramalho, Teodorico De Castro
dc.contributor.advisor1.fl_str_mv Santos, Marcelo Henrique Dos
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/7902755866146161
contributor_str_mv Viegas Junior, Cláudio
Dias, Amanda Latercia Tranches
Ramalho, Teodorico De Castro
Santos, Marcelo Henrique Dos
dc.subject.por.fl_str_mv Benzofenonas
Bacterias
Fungos
Leishmania
topic Benzofenonas
Bacterias
Fungos
Leishmania
QUIMICA::QUIMICA ORGANICA
dc.subject.cnpq.fl_str_mv QUIMICA::QUIMICA ORGANICA
description The benzophenones are used largely as synthetic intermediary in the chemical and pharmaceutical industry. They are objective of continuous investigations of biological interest due to properties, such as: insecticide, anti-aggregation platelet, inhibitory of xanthine oxidase, antioxidant, anti-microbial, anti-inflammatory and anti-proliferative. In this work it is described the synthesis of the methyl, butyl and prenyl derivatives of the benzofenones 2,4-di-hydroxybenzofenone, 4-hydroxybenzofenone and 4,4'-di-hydroxybenzofenone, following by the characterization for techniques spectroscopic and spectrometric (infrared, ultraviolet-visible and nuclear magnetic resonance and mass spectrometry). The compounds were submitted to the tests of antioxidant activity for the mechanism of scavenging of free radicals DPPH, inhibitory of xanthine oxidase and anti-microbial (bacteria, fungi and Leishmania) in order to link the chemical structure with the biological activity of the analyzed compositions. Flowed tested they didn't present significant results for the antioxidant activity in relation to the ascorbic acid pattern, once the substitutions increased the lipophilic character of the molecules in relation to the ascorbic acid pattern. In the test of inhibition of xanthine oxidase, flowed obtained they were not appraised due to yours no solubility in the middle. For the anti-bacterial (Gram-positive and Gram-negatives) activity, derived them didn't also present inhibitory activity in the tested microorganisms. In the activity anti-fungal, the butyl derivative was more active than the fluconazole. In the activity leishmanicida (promastigote form), the methyl and prenyl derivatives presented significant inhibitory activity when compared to amphotericin-B. The obtained results evidenced that the variation of the lipophilicity of the molecules is an important point for the biological activity and that some structural modifications accomplished in the benzofenonas took her flowed more potent, selective and little toxic against different types of microorganisms pathogenic.
publishDate 2012
dc.date.issued.fl_str_mv 2012-02-29
dc.date.accessioned.fl_str_mv 2015-06-10T00:18:16Z
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dc.identifier.citation.fl_str_mv MACIEL-REZENDE, Claudia Mara. Síntese de derivados benzofenônicos com potencial antifúngico e anti-leishmania. 2012. 138 f. Dissertação (Mestrado em Química) - Universidade Federal de Alfenas, Alfenas, MG, 2012.
dc.identifier.uri.fl_str_mv https://repositorio.unifal-mg.edu.br/handle/123456789/359
identifier_str_mv MACIEL-REZENDE, Claudia Mara. Síntese de derivados benzofenônicos com potencial antifúngico e anti-leishmania. 2012. 138 f. Dissertação (Mestrado em Química) - Universidade Federal de Alfenas, Alfenas, MG, 2012.
url https://repositorio.unifal-mg.edu.br/handle/123456789/359
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