Síntese e avaliação da atividade antibacteriana de Chalconas Preniladas
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Data
2023-04-06
Autores
Crespo, Beatriz Gonçalves Oliveira
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Universidade Estadual Paulista (Unesp)
Resumo
As bactérias são microrganismos, que se encontram em praticamente todos os ambientes da Terra. Elas podem ser benéficas, como aquelas que vivem no intestino e ajudam na digestão, ou podem ser patogênicas, causando doenças em humanos, animais e plantas. As doenças causas por bactérias podem ser mais simples, como infecções de garganta até mais graves e potencialmente fatais, como pneumonia bacteriana. Em decorrência disso, o objetivo geral deste trabalho é a síntese e avaliação de chalconas preniladas, afim de estudar a relação de estrutura e atividade antibacteriana. Estruturalmente, os compostos foram planejados sobre o protótipo 4’-hidroxi-4-O-geranilchalcona Assim sendo, 10 análogos chalcônicos foram propostos para serem sintetizados em duas séries, sendo a série I com modificações no anel A, com variações na posição da hidroxila, e a série II com modificações no anel B, variando as posições de diferentes grupos prenilas (isoprenila, geranila e farnesila). As sínteses foram realizadas em duas etapas, sendo a primeira envolveu uma reação de O-prenilação de derivados hidroxibenzaldeídicos, os quais foram submetidos à uma reação de condensação aldólica de Claisen-Schmidt com hidroxiacetofenonas. Após a síntese dos compostos foram realizados métodos cromatográficos para a purificação e técnicas de Ressonância Magnética Nuclear (RMN) para a identificação estrutural. Em seguida, os compostos foram enviados pra ensaios biológicos para testar a atividade antibacteriana em Gram positivas e Gram negativas.
Bacteria are microorganisms that are found in virtually all environments on Earth. They can be beneficial, such as those that live in the gut and aid in digestion, or they can be pathogenic, causing disease in humans, animals, and plants. Diseases caused by bacteria can range from simple, such as throat infections, to more serious and potentially fatal, such as bacterial pneumonia. As a result, the overall objective of this work is the synthesis and evaluation of prenylated chalcones in order to study the structure-activity relationship for antibacterial activity. Structurally, the compounds were designed based on the prototype 4'-hydroxy-4-O-geranylchalcone. Accordingly, 10 chalcone analogs were proposed to be synthesized in two series, with series I containing modifications to ring A, varying the position of the hydroxyl group, and series II containing modifications to ring B, varying the positions of different prenyl groups (isoprenyl, geranyl, and farnesyl). Syntheses were carried out in two steps, with the first involving an O-prenylation reaction of hydroxybenzaldehyde derivatives, which were then subjected to a Claisen-Schmidt aldol condensation reaction with hydroxyacetophenones. After synthesis, chromatographic methods were used for purification and Nuclear Magnetic Resonance (NMR) techniques for structural identification. The compounds were then subjected to biological assays to test their antibacterial activity against Gram-positive and Gram-negative bacteria
Bacteria are microorganisms that are found in virtually all environments on Earth. They can be beneficial, such as those that live in the gut and aid in digestion, or they can be pathogenic, causing disease in humans, animals, and plants. Diseases caused by bacteria can range from simple, such as throat infections, to more serious and potentially fatal, such as bacterial pneumonia. As a result, the overall objective of this work is the synthesis and evaluation of prenylated chalcones in order to study the structure-activity relationship for antibacterial activity. Structurally, the compounds were designed based on the prototype 4'-hydroxy-4-O-geranylchalcone. Accordingly, 10 chalcone analogs were proposed to be synthesized in two series, with series I containing modifications to ring A, varying the position of the hydroxyl group, and series II containing modifications to ring B, varying the positions of different prenyl groups (isoprenyl, geranyl, and farnesyl). Syntheses were carried out in two steps, with the first involving an O-prenylation reaction of hydroxybenzaldehyde derivatives, which were then subjected to a Claisen-Schmidt aldol condensation reaction with hydroxyacetophenones. After synthesis, chromatographic methods were used for purification and Nuclear Magnetic Resonance (NMR) techniques for structural identification. The compounds were then subjected to biological assays to test their antibacterial activity against Gram-positive and Gram-negative bacteria
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Palavras-chave
Antibacteriana, Chalconas preniladas, Cromatografia, Antibacterial, Prenyl chalcone, Chromatography