Síntese de amidas bromadas derivadas de aroilacetonitrilas com potencial atividade antimicrobiana
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Tipo
TCC
Data de publicação
2024-12
Periódico
Citações (Scopus)
Autores
Marques, Flávio de Oliveira
Orientador
Saavedra, Manuel Salustiano Almeida
Título da Revista
ISSN da Revista
Título de Volume
Membros da banca
Programa
Resumo
A resistência de bactérias a antibióticos é um problema global de saúde pública. Em
razão disso, existe grande procura por compostos alternativos para tratamento de
infecções por bactérias resistentes. Há algumas referências na literatura sobre a
utilização do bromo molecular (Br2) para a síntese de compostos com potencial
antimicrobiano. Contudo, o Br2 é uma molécula de manipulação dificultosa, além de
ter efeitos nocivos e possivelmente citotóxicos. Assim, para ser utilizado
terapeuticamente, o Br2 deve ser ligado a carreadores adequados, que viabilizem a
metabolização da molécula sem efeitos negativos. As amidas, de outro lado,
representam um grupo funcional com ampla utilização na produção de fármacos, na
medida em que podem ser facilmente metabolizadas para a entrega de moléculas
com elevado potencial bioativo. Diante desse cenário, no presente trabalho foram
sintetizadas seis amidas bromadas (2-bromo-3-(furan-2-oil)-3-oxo-propanamida, cuja
síntese já fora previamente realizada; 2,2-dibromo-3-furan-2-il-3-oxo-propanamida; 2-
bromo-3-oxo-3-fenil-propanamida; 2,2-dibromo-3-oxo-3-fenil- propanamida; 2-bromo 3-(2-hidroxi-fenil)-3-oxo-propanamida; 2-bromo-3-(3,4-dimetoxi-fenil)-3-oxo propanamida), estabelecendo-se uma nova via sintética, consistente na utilização de
família de moléculas denominada aroilacetonitrilas, que oferece maior praticidade na
síntese. Posteriormente, foi analisado e confirmado o potencial antimicrobiano da 2-
bromo-3-(furan-2-oil)-3-oxo-propanamida, via método de microdiluição em poços para
estabelecimento do CIM e da CBM.
Bacterial resistance to antibiotics is a global public health issue. Consequently, there is significant interest in alternative compounds with the potential to treat infections caused by resistant bacteria. There are references in the literature highlighting the use of molecular bromine (Br₂) in the synthesis of compounds with antimicrobial potential. However, Br₂ is a challenging molecule to handle, with harmful and potentially cytotoxic effects. Therefore, for therapeutic use, Br₂ must be bound to suitable carriers that enable its metabolization without adverse effects. Amides, on the other hand, represent a functional group widely used in drug production, as they can be easily metabolized to deliver molecules with high bioactive potential. In this context, six brominated amides were synthesized in the present work (2-bromine-3-(furan-2-yl)-3- oxopropanamide, whose synthesis had already been previously performed; 2,2- dibromine-3-(furan-2-yl)-3-oxopropanamide; 2-bromine-3-oxo-3-phenylpropanamide; 2,2-dibromine-3-oxo-3-phenylpropanamide; 2-bromine-3-(2-hydroxyphenyl)-3- oxopropanamide; 2- bromine -3-(3,4-dimethoxyphenyl)-3-oxopropanamide), via a new synthetic pathway using a family of molecules known as aroylacetonitriles, which offers greater practicality in synthesis. Subsequently, the antimicrobial potential of 2-bromo 3-(furan-2-yl)-3-oxopropanamide was analyzed and confirmed using the microdilution method in wells to determine the MIC and MBC.
Bacterial resistance to antibiotics is a global public health issue. Consequently, there is significant interest in alternative compounds with the potential to treat infections caused by resistant bacteria. There are references in the literature highlighting the use of molecular bromine (Br₂) in the synthesis of compounds with antimicrobial potential. However, Br₂ is a challenging molecule to handle, with harmful and potentially cytotoxic effects. Therefore, for therapeutic use, Br₂ must be bound to suitable carriers that enable its metabolization without adverse effects. Amides, on the other hand, represent a functional group widely used in drug production, as they can be easily metabolized to deliver molecules with high bioactive potential. In this context, six brominated amides were synthesized in the present work (2-bromine-3-(furan-2-yl)-3- oxopropanamide, whose synthesis had already been previously performed; 2,2- dibromine-3-(furan-2-yl)-3-oxopropanamide; 2-bromine-3-oxo-3-phenylpropanamide; 2,2-dibromine-3-oxo-3-phenylpropanamide; 2-bromine-3-(2-hydroxyphenyl)-3- oxopropanamide; 2- bromine -3-(3,4-dimethoxyphenyl)-3-oxopropanamide), via a new synthetic pathway using a family of molecules known as aroylacetonitriles, which offers greater practicality in synthesis. Subsequently, the antimicrobial potential of 2-bromo 3-(furan-2-yl)-3-oxopropanamide was analyzed and confirmed using the microdilution method in wells to determine the MIC and MBC.
Descrição
Palavras-chave
resistência bacteriana , bromo , síntese orgânica , amida , acetonitrilas , bacterial resistance , bromine , organic synthesis , amide , acetonitriles