Síntese de tiossemicarbazonas aldeídicas e cetônicas derivadas do (-)-cafeno

Detalhes bibliográficos
Autor(a) principal: Coelho, Narcimário Pereira
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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spelling 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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