Synthesis of chalcones by Claisen Schmidt condensation : a study of structure versus biological activities relationship

Autor: Souza, Gabriella Barroso
Přispěvatelé: Alves, Péricles Barreto, Barreiros, André Luís Bacelar Silva
Jazyk: portugalština
Rok vydání: 2019
Předmět:
Zdroj: Repositório Institucional da UFS
Universidade Federal de Sergipe (UFS)
instacron:UFS
Popis: Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPq The diversity of neglected tropical diseases (NTDs) has become a major threat, causing millions of people to die annually reported by World Health Organization (WHO).Climate change, urbanization, the incorrect treatment of domestic and industrial wastes and the use of insecticides has been some of the factors that contribute to the occurrence of these diseases. The application of chemical compounds which present pharmacological potential activity has been shown as an efficient alternative for the treatment and prevention of several health problems. In this context, synthesized chalcones are considered promising molecules, once they have been widely used in the development of prototypes for the production of drugs, due to its range of biological activities. Aiming to contribute on the development of synthesized molecules and with the study structure versus activity of bioactive substances, this study performed the synthesis and characterization by spectroscopic and chromatographic techniques ten chalcones obtained by Claisen Schmidt condensation: (E)-1,3-diphenyl-prop-2-en-1-one (C-1), (E)-1-phenyl-3-(4-methoxyphenyl)-prop-2-en-1-one) (C-2), (E)-1-(4-methoxyphenyl)-3-phenyl-prop-2-en-1-one (C-3), (E)-1-(benzo[d]-[1,3]-dioxol-6-yl)-3-(4-methoxyphenyl)-prop-2-en-1-one (C-4), (E)-1-phenyl-3-α-naphthylprop-2-en-1-one (C-5), (E)-1-(4-methoxyphenyl)-3-α-naphthylprop-2-en-1-one (C-6), (E)-1,3-Bis-(4-methoxyphenyl)-prop-2-en-1-one (C-7), (E)-1-(benzo [d] -[1,3] dioxol-6-yl)-3-α-naphthylprop-2-en-1-one (C-8), (E)-1-(4-methoxyphenyl)-3-(2-furanyl) prop-2-en-1-one (C-9) and (E)-1-(benzo[d]-[1,3]dioxol-6-yl)-3-(2-furanyl)-prop-2-en-1-one (C-10), the last unpublished. The chalcones were subjected to larvicidal tests, anti-protozoal, antibacterial and antifungal activity. In all the tests, the biological activities of these substances associated to presence of the aromatic rings attached to the enone, their substituents and their respective ring positions. A diversidade de doenças tropicais negligenciadas (DTN) tornou-se uma grande ameaça, levando milhões de pessoas a óbito. Os principais fatores que contribuem para a ocorrência dessas enfermidades são mudanças climáticas, falta de planejamento urbano, ausência de saneamento básico e o uso indiscriminado de inseticidas. A utilização de agentes químicos com elevados potenciais farmacodinâmicos mostra-se uma alternativa eficaz no tratamento e prevenção de diversos problemas de saúde. Neste contexto, chalconas sintéticas são moléculas promissoras no desenvolvimento de protótipos para obtenção de fármacos, devido à sua gama de atividades biológicas. Buscando contribuir com a diversidade de moléculas sintéticas e com o estudo estrutura versus atividade de substâncias bioativas, este trabalho visou à síntese e caracterização por técnicas espectroscópicas e cromatográficas de uma série de chalconas obtidas por condensação de Claisen- Schmidt. São elas: (E)-1,3-difenil-prop-2-en-1-ona (C-1), (E)-1-fenil-3-(4-metoxifenil)-prop-2-en-1-ona (C-2), (E)-1-(4-metoxifenil)-3-fenil-prop-2-en-1-ona (C-3), (E)-1-(benzo[d]-[1,3]dioxol-6-il)-3-(4-metoxifenil)-prop-2-en-1-ona (C-4), (E)-1-fenil-3-α-naftilprop-2-en-1-ona (C-5), (E)-1-(4-metoxifenil)-3-α-naftilprop-2-en-1-ona (C-6), (E)-1,3-Bis-(4-metoxifenil)-prop-2-en-1-ona (C-7), (E)-1-(benzo[d]-[1,3]dioxol-6-il)-3-α-naftilprop-2-en-1-ona (C-8), (E)-1-(4-metoxifenil)-3-(2-furanil)-prop-2-en-1-ona (C-9) e (E)-1-(benzo[d]-[1,3]dioxol-6-il)-3-(2-furanil)-prop-2-en-1-ona (C-10), sendo a última inédita. As chalconas sintetizadas foram submetidas a testes de atividade larvicida, anti-protozoária, antibactericida e antifúngica. Em todos os ensaios mencionados, as atividades biológicas dessas substâncias relacionaram-se com a presença dos anéis aromáticos ligados à enona, seus substituintes e suas respectivas posições no anel. São Cristóvão, SE
Databáze: OpenAIRE
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