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Abstract(s)
As reações químicas são utilizadas desde a antiguidade e ao longo dos anos novos conhecimentos têm sido adquiridos, permitindo assim melhorar os processos já existentes e a criação de novos métodos para serem aplicados nas mais diversas áreas científicas.
Este trabalho descreve a obtenção de produtos derivados da carvona, composto com abundância natural, através de reações com tricloreto de alumínio e peróxido de hidrogénio, n-bromosuccinimida e ácido p-toluenosulfónico, utilização dos catalisadores l-prolina, quinina, quinidina e difenilprolinol e por fim reações de epoxidação com carbonato de potássio. Nas reações realizadas obtiveram-se diversos compostos, num total de 21, contudo alguns desses compostos são já conhecidos bibliograficamente. Apenas 8 destes compostos são novos e descritos pela primeira vez. Os novos compostos obtidos neste trabalho são, essencialmente, bromoderivados da carvona que contêm também o grupo nitrobenzeno. Estas adições ocorreram na presença de catalisador permitindo assim uma melhor receção dos grupos -Br provenientes da n-bromosuccinimida.
De modo a verificar a eficácia dos catalisadores, estes foram aplicados em reações que utilizaram com produto de partida guaiol ou bulnesol, contudo o resultados destas reações foram muito inconclusivos, uma vez que as frações obtidas apresentavam misturas bastante complexas e quase impossíveis de separar, estando-se ainda a analisar estas misturas pelas técnica de GC-MS, de modo a descobrir quais as suas massas e depois chegar a possíveis conclusões.
Foi também realizado o estudo da atividade biológica de 8 produtos obtidos nas reações com carvona, incluindo de 4 dos novos compostos obtidos e ainda utilizando guaiol, bulnesol e águas mães (essência bruta obtida da planta Bulnesia sarmientoi da qual se obtém o guaiol e o bulnesol). As atividades realizadas foram: atividade antioxidante frente a 2,2-difenil-1-picrilhidrazilo (DPPH), avaliação da capacidade de remoção do anião superóxido (em sistema não enzimático e em anéis de aorta) e por fim atividade cardiovascular.
The chemical reactions are used since antiquity and over the years new knowledge has been acquired, for improving processes that existing and create new methods to be applied in various scientific fields. This work describes the production of naturally occurring carvone derivatives through reactions with aluminum trichloride and hydrogen peroxide, n-bromosuccinimide and p-toluenesulfonic acid, the use of the L-proline, quinine, quinidine and diphenylprolinol catalysts and finally epoxidation reactions with potassium carbonate. In the reactions performed several compounds were obtained, for a total of 21, however some of these compounds are already known bibliographically. Only 8 of these compounds are new and described for the first time. The new compounds obtained in this work are essentially brominated derivatives of the carvone which also contain the nitrobenzene group. These additions occurred in the presence of catalyst thus allowing better reception of the -Br groups from n-bromosuccinimide. To verify the effectiveness of the catalysts, these were applied in reactions using guaiol or bulnesol starting materials, however the results of these reactions were very inconclusive, since the obtained fractions presented very complex and almost impossible to separate mixtures, being and to analyze these mixtures by GC-MS techniques, in order to find out their masses and then reach possible conclusions. It was also carried out the study of the biological activity of 8 products obtained in the reactions with carvone, including 4 of the new compounds obtained and still using guaiol, bulnesol and mother waters (crude essence from which guaiol and bulnesol are obtained). The activities performed were: antioxidant activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH), evaluation of the ability to remove superoxide anion (in a non-enzymatic system and in aortic rings) and finally cardiovascular atrocity.
The chemical reactions are used since antiquity and over the years new knowledge has been acquired, for improving processes that existing and create new methods to be applied in various scientific fields. This work describes the production of naturally occurring carvone derivatives through reactions with aluminum trichloride and hydrogen peroxide, n-bromosuccinimide and p-toluenesulfonic acid, the use of the L-proline, quinine, quinidine and diphenylprolinol catalysts and finally epoxidation reactions with potassium carbonate. In the reactions performed several compounds were obtained, for a total of 21, however some of these compounds are already known bibliographically. Only 8 of these compounds are new and described for the first time. The new compounds obtained in this work are essentially brominated derivatives of the carvone which also contain the nitrobenzene group. These additions occurred in the presence of catalyst thus allowing better reception of the -Br groups from n-bromosuccinimide. To verify the effectiveness of the catalysts, these were applied in reactions using guaiol or bulnesol starting materials, however the results of these reactions were very inconclusive, since the obtained fractions presented very complex and almost impossible to separate mixtures, being and to analyze these mixtures by GC-MS techniques, in order to find out their masses and then reach possible conclusions. It was also carried out the study of the biological activity of 8 products obtained in the reactions with carvone, including 4 of the new compounds obtained and still using guaiol, bulnesol and mother waters (crude essence from which guaiol and bulnesol are obtained). The activities performed were: antioxidant activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH), evaluation of the ability to remove superoxide anion (in a non-enzymatic system and in aortic rings) and finally cardiovascular atrocity.
Description
Keywords
Carvona Guaiol Bulnesol Organocatálise Atividade Biológica