Orientador: Prof. Dr. Anderson Orzari Ribeiro / Tese (doutorado) - Universidade Federal do ABC. Programa de Pós-Graduação em Ciência e Tecnologia/Química, 2016. / Este trabalho descreve a sintese de butadienos push-pull. Utilizou-se as reacoes de Vilsmeier-Haack para a obtencao de clorovinilaldeidos e posteriormente a reacao de Knoevenagel, obtendo-se assim os butadienos push-pull, que sao compostos de elevada conjugacao eletronica. Alem dos butadienos push-pull, obteve-se atraves de uma reacao de condensacao aldolica, catalisada por acido, uma nova pentadienona, a 2,6-bis-(4-hidroxi-3-metoxi-benziliden)-cicloexanona e uma tetraen-5-ona, a 9-dicloro-1,9-bis-(3,4-dimetoxi-fenil)-nona-1,3,6,8-tetraen-5-ona. Realizou-se a caracterizacao estrutural de todos esses compostos, confirmando-se assim a estrutura dos mesmos. Testou-se estes compostos a respeito de suas propriedades antioxidantes, bactericidas e fungicidas. O composto 2,6-bis-(4-hidroxi-3-metoxi-benziliden)-cicloexanona demonstrou elevada atividade antioxidante na concentracao de 260 ¿Êg/mL quando comparado com a quercetina, que e um fenol utilizado como padrao no teste de DPPH. Realizou-se dois testes de atividade bactericida e fungicida e os compostos apresentaram halo de inibicao a diversos micro-organismos sendo que o composto 2,6-bis-(4-hidroxi-3-metoxi-benziliden)-cicloexanona demonstrou ser o mais promissor, inibindo o crescimento de 7 das 9 especies de micro-organismos testados. / This work describes the synthesis of push-pull butadienes. The Vilsmeier-Haack reactions were used to obtain chloro-vinyl-aldehydes and later the Knoevenagel reaction to obtain the push-pull butadienes, which are compounds of high electronic conjugation. In addition to push-pull butadiene, applying acid catalyzed aldol condensation, new pentadienones were obtained, like 2,6-bis-(4-hydroxy-3-methoxy-benzylidene)¿cyclohexanone and a 9-dichloro-1,9-bis-(3,4-dimethoxy-phenyl)-1,3,6,8-tetraen-5-one. The structural characterization was carried out, confirming the structure the synthesized compounds. The compounds were tested for their antioxidant, bactericidal and fungicidal properties. The 2,6-bis-(4-hydroxy-3-methoxy-benzylidene) -cyclohexanone showed a high antioxidant activity at 260 ìg/mL when compared to quercetin, which is a phenol used as a standard in the DPPH test. They showed inhibition to several microorganisms and the compound, 2,6-bis- (4-hydroxy-3-methoxy-benzylidene) -cyclohexanone was the most promising, inhibiting the growth of 7 of the 9 species of microorganisms tested.
| Identifer | oai:union.ndltd.org:IBICT/oai:BDTD:105722 |
| Date | January 2016 |
| Creators | Santos, Reginaldo Pereira |
| Contributors | Ribeiro, Anderson Orzari, Suárez, José Agustín Quincoces |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/doctoralThesis |
| Format | application/pdf, 246 f. : il. |
| Source | reponame:Repositório Institucional da UFABC, instname:Universidade Federal do ABC, instacron:UFABC |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | http://biblioteca.ufabc.edu.br/index.php?codigo_sophia=105722&midiaext=74124, http://biblioteca.ufabc.edu.br/index.php?codigo_sophia=105722&midiaext=74125, Cover: http://biblioteca.ufabc.edu.brphp/capa.php?obra=105722 |
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