Síntese de tiossemicarbazonas aldeídicas e cetônicas derivadas do (-)-cafeno
Autor(a) principal: | |
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Data de Publicação: | 2011 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional da Universidade Estadual de Maringá (RI-UEM) |
Texto Completo: | http://repositorio.uem.br:8080/jspui/handle/1/3904 |
Resumo: | The thiosemicarbazones are molecules that present large shape of biological activities, the changing with alkyl or aryl group is common in position N-1, but are rare cases of terpene substituents on nitrogen terminal N-4. Before these facts, our research group has begun the synthesis of new thiosemicarbazones with terpene unities in N-4. In continuing to the synthesis of thiosemicarbazones derived from menoterpene (-) ? camphene, the present paper describes the synthesis` conclusion from new thiosemicarbazones aldehydic range (m-metoxi-p-hidroxi (32a), p-fluor (32b), ohidroxi (32c) benzaldehyde thiosemicarbazone) and benzene thiosemicarbazone (34)), and an unprecedented range of thiosemicarbazone derived from heterocyclic aldehyde (2-phurane (33a), 2-pyrrole (33b), 2- thiophene (33c) carboxaldehyde thiosemicarbazone), and beyond the synthesis of thiosemicarbazone derived from cinnamaldehyde, menthone and ethyl pyruvate (cinnamal thiosemicarbazone (35), menthene thiosemicarbazone (36) and ethyl thiosemicarbazone (37) The achievement of thiosemicarbazone was done trough the condensation of thiosemicarbazone derived of (-)-camphene, with various carbonyl compound using methodology adapted from literature and a new methodology using gel of silica catalyst with H2SO4 . Before the difference in the reactions time to the achievement of thiosemicarbazone derived of (-)- camphene, R-(+)-limonene and of N-bisabolol were done computational theoretical calculation to analyze the reaction intermediate from the addition of hydrazine to the different isothiocyanate ((-)-camphene, R-(+)-limonene and of N-bisabolol). The thiosemicarbazone sinthetyze (31a-37) were submitted to an initial choice to the evaluation of antitumor activity before the cells of melanoma SKMEL-37, which the thiosemicarbazone (31a, 31c, 31e, 32a-c, 33a, 33c e 37) that induced to the higher mortality of cancer cells were separated to the continuing of studies. |
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Síntese de tiossemicarbazonas aldeídicas e cetônicas derivadas do (-)-cafenoIsotiocianatos(-)-CanfenoAldeídosCetonasTiossemicarbazonasTerpenosAtividade antitumoralBrasil.ThiosemicarbazoneTerpen.e isothiocyanate(-)- CampheneAntitumor activityBrazil.Ciências Exatas e da TerraQuímicaThe thiosemicarbazones are molecules that present large shape of biological activities, the changing with alkyl or aryl group is common in position N-1, but are rare cases of terpene substituents on nitrogen terminal N-4. Before these facts, our research group has begun the synthesis of new thiosemicarbazones with terpene unities in N-4. In continuing to the synthesis of thiosemicarbazones derived from menoterpene (-) ? camphene, the present paper describes the synthesis` conclusion from new thiosemicarbazones aldehydic range (m-metoxi-p-hidroxi (32a), p-fluor (32b), ohidroxi (32c) benzaldehyde thiosemicarbazone) and benzene thiosemicarbazone (34)), and an unprecedented range of thiosemicarbazone derived from heterocyclic aldehyde (2-phurane (33a), 2-pyrrole (33b), 2- thiophene (33c) carboxaldehyde thiosemicarbazone), and beyond the synthesis of thiosemicarbazone derived from cinnamaldehyde, menthone and ethyl pyruvate (cinnamal thiosemicarbazone (35), menthene thiosemicarbazone (36) and ethyl thiosemicarbazone (37) The achievement of thiosemicarbazone was done trough the condensation of thiosemicarbazone derived of (-)-camphene, with various carbonyl compound using methodology adapted from literature and a new methodology using gel of silica catalyst with H2SO4 . Before the difference in the reactions time to the achievement of thiosemicarbazone derived of (-)- camphene, R-(+)-limonene and of N-bisabolol were done computational theoretical calculation to analyze the reaction intermediate from the addition of hydrazine to the different isothiocyanate ((-)-camphene, R-(+)-limonene and of N-bisabolol). The thiosemicarbazone sinthetyze (31a-37) were submitted to an initial choice to the evaluation of antitumor activity before the cells of melanoma SKMEL-37, which the thiosemicarbazone (31a, 31c, 31e, 32a-c, 33a, 33c e 37) that induced to the higher mortality of cancer cells were separated to the continuing of studies.As tiossemicarbazonas são moléculas que apresentam amplo perfil de atividades biológicas, a substituição com grupos alquila ou arila é comum na posição N-1, porém são raros os casos de substituintes terpênicos no nitrogênio terminal N-4. Diante destes fatos, nosso grupo de pesquisa iniciou a síntese de novas tiossemicarbazonas com unidades terpênicas em N-4. Em continuidade à síntese de tiossemicarbazonas derivadas do monoterpeno (-)- canfeno, o presente trabalho descreve a finalização da síntese da série de novas tiossemicarbazonas aldeídicas (m-metoxi-p-hidroxi (32a), p-flúor (32b) o-hidroxi (32c) benzaldeídotiossemicarbazonas), a síntese de novas tiossemicarbazonas cetônicas (acetofenona (31a), p-nitro (31b), p-cloro (31c), p-metoxi (31d), p-metil (31e), p-fluor (31f) e p-hidroxi (31g) acetofenonastiossemcarbazonas) e benzofenonatiossemicarbazona (34)), e uma série inédita de tiossemicarbazonas derivadas de aldeídos heterocíclicos (2-furano (33a), 2-pirrol (33b), 2-tiofeno (33c) carboxaldeídotiossemicarbazonas), e mais a síntese das tiossemicarbazonas derivadas do cinamaldeído, mentona e do etil-piruvato (cinamaldeídotiossemicarbazona (35), mentonatiossemicarbazona (36) e etilpiruvatotiossemicarbazona (37) A obtenção das tiossemicarbazonas foi realizada através da condensação da tiossemicarbazida derivada do (-)-canfeno, com diversos compostos carbonílicos empregando-se metodologia adaptada da literatura e uma nova metodologia utilizando gel de sílica catalisada com H2SO4. Diante da diferença nos tempos reacionais para obtenção das tiossemicarbazidas derivadas do (-)-canfeno, R-(+)-limonento e do N-bisabolol foram realizados cálculos teóricos computacionais para analisar o intermediário reacional da adição da hidrazina aos diferentes isotiocianatos ((-)-canfeno, R-(+)-limoneno e do N-bisabolol). As tiossemicarbazonas sintetizadas (31a-37) foram submetidas a uma triagem inicial para avaliação da atividade antitumoral frente a células de melanoma SKMEL-37, sendo que as tiossemicarbazonas (31a, 31c, 31e, 32a-c, 33a, 33c e 37) que levaram à maior mortalidade das células cancerígenas foram separadas para continuidade dos estudos.vi, 127 fUniversidade Estadual de MaringáBrasilDepartamento de QuímicaPrograma de Pós-Graduação em QuímicaUEMMaringá, PRCentro de Ciências ExatasCleuza Conceição da SilvaGisele de Freitas Gauze Bandoch - UEMAntonio Laverde Junior - UNIPARCoelho, Narcimário Pereira2018-04-17T17:52:57Z2018-04-17T17:52:57Z2011info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesishttp://repositorio.uem.br:8080/jspui/handle/1/3904porinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da Universidade Estadual de Maringá (RI-UEM)instname:Universidade Estadual de Maringá (UEM)instacron:UEM2018-10-15T19:23:24Zoai:localhost:1/3904Repositório InstitucionalPUBhttp://repositorio.uem.br:8080/oai/requestopendoar:2024-04-23T14:57:03.721392Repositório Institucional da Universidade Estadual de Maringá (RI-UEM) - Universidade Estadual de Maringá (UEM)false |
dc.title.none.fl_str_mv |
Síntese de tiossemicarbazonas aldeídicas e cetônicas derivadas do (-)-cafeno |
title |
Síntese de tiossemicarbazonas aldeídicas e cetônicas derivadas do (-)-cafeno |
spellingShingle |
Síntese de tiossemicarbazonas aldeídicas e cetônicas derivadas do (-)-cafeno Coelho, Narcimário Pereira Isotiocianatos (-)-Canfeno Aldeídos Cetonas Tiossemicarbazonas Terpenos Atividade antitumoral Brasil. Thiosemicarbazone Terpen.e isothiocyanate (-)- Camphene Antitumor activity Brazil. Ciências Exatas e da Terra Química |
title_short |
Síntese de tiossemicarbazonas aldeídicas e cetônicas derivadas do (-)-cafeno |
title_full |
Síntese de tiossemicarbazonas aldeídicas e cetônicas derivadas do (-)-cafeno |
title_fullStr |
Síntese de tiossemicarbazonas aldeídicas e cetônicas derivadas do (-)-cafeno |
title_full_unstemmed |
Síntese de tiossemicarbazonas aldeídicas e cetônicas derivadas do (-)-cafeno |
title_sort |
Síntese de tiossemicarbazonas aldeídicas e cetônicas derivadas do (-)-cafeno |
author |
Coelho, Narcimário Pereira |
author_facet |
Coelho, Narcimário Pereira |
author_role |
author |
dc.contributor.none.fl_str_mv |
Cleuza Conceição da Silva Gisele de Freitas Gauze Bandoch - UEM Antonio Laverde Junior - UNIPAR |
dc.contributor.author.fl_str_mv |
Coelho, Narcimário Pereira |
dc.subject.por.fl_str_mv |
Isotiocianatos (-)-Canfeno Aldeídos Cetonas Tiossemicarbazonas Terpenos Atividade antitumoral Brasil. Thiosemicarbazone Terpen.e isothiocyanate (-)- Camphene Antitumor activity Brazil. Ciências Exatas e da Terra Química |
topic |
Isotiocianatos (-)-Canfeno Aldeídos Cetonas Tiossemicarbazonas Terpenos Atividade antitumoral Brasil. Thiosemicarbazone Terpen.e isothiocyanate (-)- Camphene Antitumor activity Brazil. Ciências Exatas e da Terra Química |
description |
The thiosemicarbazones are molecules that present large shape of biological activities, the changing with alkyl or aryl group is common in position N-1, but are rare cases of terpene substituents on nitrogen terminal N-4. Before these facts, our research group has begun the synthesis of new thiosemicarbazones with terpene unities in N-4. In continuing to the synthesis of thiosemicarbazones derived from menoterpene (-) ? camphene, the present paper describes the synthesis` conclusion from new thiosemicarbazones aldehydic range (m-metoxi-p-hidroxi (32a), p-fluor (32b), ohidroxi (32c) benzaldehyde thiosemicarbazone) and benzene thiosemicarbazone (34)), and an unprecedented range of thiosemicarbazone derived from heterocyclic aldehyde (2-phurane (33a), 2-pyrrole (33b), 2- thiophene (33c) carboxaldehyde thiosemicarbazone), and beyond the synthesis of thiosemicarbazone derived from cinnamaldehyde, menthone and ethyl pyruvate (cinnamal thiosemicarbazone (35), menthene thiosemicarbazone (36) and ethyl thiosemicarbazone (37) The achievement of thiosemicarbazone was done trough the condensation of thiosemicarbazone derived of (-)-camphene, with various carbonyl compound using methodology adapted from literature and a new methodology using gel of silica catalyst with H2SO4 . Before the difference in the reactions time to the achievement of thiosemicarbazone derived of (-)- camphene, R-(+)-limonene and of N-bisabolol were done computational theoretical calculation to analyze the reaction intermediate from the addition of hydrazine to the different isothiocyanate ((-)-camphene, R-(+)-limonene and of N-bisabolol). The thiosemicarbazone sinthetyze (31a-37) were submitted to an initial choice to the evaluation of antitumor activity before the cells of melanoma SKMEL-37, which the thiosemicarbazone (31a, 31c, 31e, 32a-c, 33a, 33c e 37) that induced to the higher mortality of cancer cells were separated to the continuing of studies. |
publishDate |
2011 |
dc.date.none.fl_str_mv |
2011 2018-04-17T17:52:57Z 2018-04-17T17:52:57Z |
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://repositorio.uem.br:8080/jspui/handle/1/3904 |
url |
http://repositorio.uem.br:8080/jspui/handle/1/3904 |
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.publisher.none.fl_str_mv |
Universidade Estadual de Maringá Brasil Departamento de Química Programa de Pós-Graduação em Química UEM Maringá, PR Centro de Ciências Exatas |
publisher.none.fl_str_mv |
Universidade Estadual de Maringá Brasil Departamento de Química Programa de Pós-Graduação em Química UEM Maringá, PR Centro de Ciências Exatas |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional da Universidade Estadual de Maringá (RI-UEM) instname:Universidade Estadual de Maringá (UEM) instacron:UEM |
instname_str |
Universidade Estadual de Maringá (UEM) |
instacron_str |
UEM |
institution |
UEM |
reponame_str |
Repositório Institucional da Universidade Estadual de Maringá (RI-UEM) |
collection |
Repositório Institucional da Universidade Estadual de Maringá (RI-UEM) |
repository.name.fl_str_mv |
Repositório Institucional da Universidade Estadual de Maringá (RI-UEM) - Universidade Estadual de Maringá (UEM) |
repository.mail.fl_str_mv |
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