Abordagem para a síntese de amidas naturais bioativas e seus análogos
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| Data de Publicação: | 2005 |
| Tipo de documento: | Dissertação |
| Idioma: | por |
| Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFRRJ |
| Texto Completo: | https://rima.ufrrj.br/jspui/handle/20.500.14407/14568 |
Resumo: | Os resultados descritos neste trabalho se inserem numa linha de pesquisa que tem como objetivo a síntese de moléculas com potencial atividade antiparasitária, a partir de precursores de origem natural. São descritas as sínteses estereosseletivas de nove (E,E)-dienamidas, análogas à amida natural piperina (isolada de Piper nigrum), com modificações no padrão de substituição do anel aromático. A abordagem sintética desenvolvida para a síntese das dienamidas, possui como etapa-chave a reação de Emmons-Horner do ânion da piperidinil-fosfonoacetamida com aldeídos adequados, preparados a partir dos alilbenzenos naturais, safrol e eugenol. A metodologia sintética estudada foi ainda aplicada na síntese de três amidas naturais: piperina, piperetina e 3,4- metilenodioxi-cinamamida, todas isoladas de espécies do gênero Piper. As novas amidas obtidas terão suas atividades tóxicas avaliadas sobre epimastigotas de Trypanosoma cruzi, protozoário flagelado, agente etiológico da doença de Chagas |
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Barreto Junior, Cleber BomfimLima, Marco Edilson Freire dehttp://lattes.cnpq.br/8392420706762318Lima, Marco Edilson Freire dePinheiro, SérgioSant'Anna, Carlos Maurício R. dehttp://lattes.cnpq.br/97348864461623032023-12-22T03:03:11Z2023-12-22T03:03:11Z2005-06-10Barreto Junior, Cleber Bomfim. Abordagem para a síntese de amidas naturais bioativas e seus análogos. 2005. 167 f. Dissertação (Programa de Pós-Graduação em Química) - Universidade Federal Rural do Rio de Janeiro, Seropédica-RJ .https://rima.ufrrj.br/jspui/handle/20.500.14407/14568Os resultados descritos neste trabalho se inserem numa linha de pesquisa que tem como objetivo a síntese de moléculas com potencial atividade antiparasitária, a partir de precursores de origem natural. São descritas as sínteses estereosseletivas de nove (E,E)-dienamidas, análogas à amida natural piperina (isolada de Piper nigrum), com modificações no padrão de substituição do anel aromático. A abordagem sintética desenvolvida para a síntese das dienamidas, possui como etapa-chave a reação de Emmons-Horner do ânion da piperidinil-fosfonoacetamida com aldeídos adequados, preparados a partir dos alilbenzenos naturais, safrol e eugenol. A metodologia sintética estudada foi ainda aplicada na síntese de três amidas naturais: piperina, piperetina e 3,4- metilenodioxi-cinamamida, todas isoladas de espécies do gênero Piper. As novas amidas obtidas terão suas atividades tóxicas avaliadas sobre epimastigotas de Trypanosoma cruzi, protozoário flagelado, agente etiológico da doença de ChagasCoordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESFundação de Amparo à Pesquisa do Estado do Rio de Janeiro - FAPERJThe results described in this thesis are part of a research project which aims at the syntheses of molecules with potential antiparasitic activity using natural products as precursors. The stereoselective syntheses of nine (E,E)-dienamides with different substitution patterns, which are analogous to natural piperine (isolated from Piper nigrum) were carried out. The synthetic approach involves, as a key step, an EmmonsHorner reaction of the piperidinylphosphonoacetamide anion with suitable aldehydes, which were in turn prepared from the natural allylbenzenes, safrole and eugenol. This synthetic methodology was further employed in the syntheses of the natural amides piperine, piperettine and 3,4-methylenedioxicynamamide, which are all found in the Piper genus. The new amides will be investigated in relation to their potential action against epimastigote forms of the protozoan Trypanosoma cruzi, the ethiological agent of the Chagas diseaseapplication/pdfporUniversidade Federal Rural do Rio de JaneiroPrograma de Pós-Graduação em QuímicaUFRRJBrasilInstituto de Ciências ExatasTrypanosoma cruziprotozoário flageladoagente etiológico da doença de ChagasDienamidesEmmons-HornerPiperamidesQuímicaAbordagem para a síntese de amidas naturais bioativas e seus análogosApproach to the Synthesis of Natural Bioactive Dienamides and Their Analoguesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisABARBRI, M.; PARRAIN, J. L.; DUCHENE, A. A Synthetic Approach to Natural Dienamides of Insecticidal Interest. Synthetic Communications, v. 28, n. 2, p. 239-249, 1998 ARAUJO, C. A. C.; ALEGRIO, L. V.; GOMES, D. C. F.; LIMA, M. E. F.; GOMESCARDOSO, L.; LEON, L. L. 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Síntese Total do Ácido Ferúlico e do Ferulato de 34-Hidroxi-Tetratriacontanila a Partir do Eugenol In: REUNIÃO ANUAL DA SOCIEDADE BRASILEIRA DE QUÍMICA, 23º. 2000, Poços de Caldas / MG. Anais... São Paulo: Sociedade Brasileira de Química, 2000. p. QO-109. SUMATHIKUTTY, M. A.; RAJARAMAN, K.; SANKARIKUTTY, B.; MATHEW, A. G. Chemical Composition of Pepper Grades and Products. Journal of Food Science and Technology-Mysore, v. 16, p. 249-254, 1979 SUNILA, E. S.; KUTTAN, G. Immunomodulatory and Antitumor Activity of Piper Longum Linn. and Piperine. Journal of Ethnopharmacology, v. 90, n. 2-3, p. 339-346, 2004 TSUBOI, S.; TAKEDA, A. New Synthesis of Piperine and Isochavicine. Tetrahedron Letters, n. 12, p. 1043-1044, 1979 TSUKAMOTO, S.; CHA, B. C.; OHTA, T. Dipiperamides A, B, and C: Bisalkaloids From the White Pepper Piper Nigrum Inhibiting CYP3A4 Activity. Tetrahedron, v. 58, n. 9, p. 1667-1671, 2002 UMBREIT, M. A.; SHARPLESS, K. B. Allylic Oxidation of Olefins by Catalytic and Stoichiometric Selenium Dioxide With Tert-Butyl Hydroperoxide. Journal of the American Chemical Society, v. 99, n. 16, p. 5526-5528, 1977 UPADHYAYA, S. D.; KANSAL, C. M.; PANDEY, N. N. Clinical Evaluation of (Piper Longum) on Patients of Bronchial Asthma - A Preliminary Study. Nagarjuna, v. 25, p. 256-258, 1982 URBINA, J. A. Chemotherapy of Chagas Disease. Current Pharmaceutical Design, v. 8, n. 4, p. 287-295, 2002 VENKATASAMY, R.; FAAS, L.; YOUNG, A. R.; RAMAN, A.; HIDER, R. C. Effects of Piperine Analogues on Stimulation of Melanocyte Proliferation and Melanocyte Differentiation. Bioorganic & Medicinal Chemistry, v. 12, n. 8, p. 1905-1920, 2004 VIODÉ, C.; BETTACHE, N.; CENAS, N.; KRAUTH-SIEGEL, R. L.; CHAUVIÈRE, G.; BAKALARA, N.; PÉRIÉ, J. Enzymatic Reduction Studies of Nitroheterocycles. Biochemical Pharmacology, v. 57, p. 549-577, 1999 167 WALKUP, R. D.; CUNNINGHAM, R. T. Studies on the Syntheses of the Aplysiatoxins - Synthesis of A Selectively-Protected Form of the C-27-C-30 (Dihydroxybutanoate) Moiety of Oscillatoxin-A. Tetrahedron Letters, v. 28, n. 35, p. 4019-4022, 1987 WILLIAMS, D. H.; FLEMING, I. Spectroscopic Methods in Organic Chemistry. 4° ed.; London: McGraw-Hill, 1989. 264p YESILADA, A.; ZORLU, E.; AKSU, F.; YESILADA, E. 3,4-Dimethoxy Cinnamic Acid Tertiary Amides: Synthesis and Evaluation of Antiinflammatory and Analgesic Activities. Farmaco, v. 51, n. 8-9, p. 595-599, 1996https://tede.ufrrj.br/retrieve/63325/2005%20-%20Cleber%20Bomfim%20Barreto%20Junior.pdf.jpghttps://tede.ufrrj.br/jspui/handle/jspui/4223Submitted by Celso Magalhaes (celsomagalhaes@ufrrj.br) on 2020-12-01T12:03:40Z No. of bitstreams: 1 2005 - Cleber Bomfim Barreto Junior.pdf: 6155253 bytes, checksum: a30005c3edee981e950169731443611e (MD5)Made available in DSpace on 2020-12-01T12:03:40Z (GMT). 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| dc.title.por.fl_str_mv |
Abordagem para a síntese de amidas naturais bioativas e seus análogos |
| dc.title.alternative.eng.fl_str_mv |
Approach to the Synthesis of Natural Bioactive Dienamides and Their Analogues |
| title |
Abordagem para a síntese de amidas naturais bioativas e seus análogos |
| spellingShingle |
Abordagem para a síntese de amidas naturais bioativas e seus análogos Barreto Junior, Cleber Bomfim Trypanosoma cruzi protozoário flagelado agente etiológico da doença de Chagas Dienamides Emmons-Horner Piperamides Química |
| title_short |
Abordagem para a síntese de amidas naturais bioativas e seus análogos |
| title_full |
Abordagem para a síntese de amidas naturais bioativas e seus análogos |
| title_fullStr |
Abordagem para a síntese de amidas naturais bioativas e seus análogos |
| title_full_unstemmed |
Abordagem para a síntese de amidas naturais bioativas e seus análogos |
| title_sort |
Abordagem para a síntese de amidas naturais bioativas e seus análogos |
| author |
Barreto Junior, Cleber Bomfim |
| author_facet |
Barreto Junior, Cleber Bomfim |
| author_role |
author |
| dc.contributor.author.fl_str_mv |
Barreto Junior, Cleber Bomfim |
| dc.contributor.advisor1.fl_str_mv |
Lima, Marco Edilson Freire de |
| dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/8392420706762318 |
| dc.contributor.referee1.fl_str_mv |
Lima, Marco Edilson Freire de |
| dc.contributor.referee2.fl_str_mv |
Pinheiro, Sérgio |
| dc.contributor.referee3.fl_str_mv |
Sant'Anna, Carlos Maurício R. de |
| dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/9734886446162303 |
| contributor_str_mv |
Lima, Marco Edilson Freire de Lima, Marco Edilson Freire de Pinheiro, Sérgio Sant'Anna, Carlos Maurício R. de |
| dc.subject.por.fl_str_mv |
Trypanosoma cruzi protozoário flagelado agente etiológico da doença de Chagas |
| topic |
Trypanosoma cruzi protozoário flagelado agente etiológico da doença de Chagas Dienamides Emmons-Horner Piperamides Química |
| dc.subject.eng.fl_str_mv |
Dienamides Emmons-Horner Piperamides |
| dc.subject.cnpq.fl_str_mv |
Química |
| description |
Os resultados descritos neste trabalho se inserem numa linha de pesquisa que tem como objetivo a síntese de moléculas com potencial atividade antiparasitária, a partir de precursores de origem natural. São descritas as sínteses estereosseletivas de nove (E,E)-dienamidas, análogas à amida natural piperina (isolada de Piper nigrum), com modificações no padrão de substituição do anel aromático. A abordagem sintética desenvolvida para a síntese das dienamidas, possui como etapa-chave a reação de Emmons-Horner do ânion da piperidinil-fosfonoacetamida com aldeídos adequados, preparados a partir dos alilbenzenos naturais, safrol e eugenol. A metodologia sintética estudada foi ainda aplicada na síntese de três amidas naturais: piperina, piperetina e 3,4- metilenodioxi-cinamamida, todas isoladas de espécies do gênero Piper. As novas amidas obtidas terão suas atividades tóxicas avaliadas sobre epimastigotas de Trypanosoma cruzi, protozoário flagelado, agente etiológico da doença de Chagas |
| publishDate |
2005 |
| dc.date.issued.fl_str_mv |
2005-06-10 |
| dc.date.accessioned.fl_str_mv |
2023-12-22T03:03:11Z |
| dc.date.available.fl_str_mv |
2023-12-22T03:03:11Z |
| 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 |
Barreto Junior, Cleber Bomfim. Abordagem para a síntese de amidas naturais bioativas e seus análogos. 2005. 167 f. Dissertação (Programa de Pós-Graduação em Química) - Universidade Federal Rural do Rio de Janeiro, Seropédica-RJ . |
| dc.identifier.uri.fl_str_mv |
https://rima.ufrrj.br/jspui/handle/20.500.14407/14568 |
| identifier_str_mv |
Barreto Junior, Cleber Bomfim. Abordagem para a síntese de amidas naturais bioativas e seus análogos. 2005. 167 f. Dissertação (Programa de Pós-Graduação em Química) - Universidade Federal Rural do Rio de Janeiro, Seropédica-RJ . |
| url |
https://rima.ufrrj.br/jspui/handle/20.500.14407/14568 |
| dc.language.iso.fl_str_mv |
por |
| language |
por |
| dc.relation.references.por.fl_str_mv |
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