Estudo de semi-sintéticos do ácido morônico e estudo de espectroscopia de difusão ordenada em produtos naturais

• Ano de defesa: 2019
• Autor(a) principal: Ferraz, Adriano
• Tipo de documento: Tese
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal de Santa Maria; Brasil; Química; UFSM; Programa de Pós-Graduação em Química; Centro de Ciências Naturais e Exatas
• Palavras-chave em Português: Ácido morônico; Derivados; Difusão ordenada; Moronic acid; Derivatives; Ordered diffusion; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/20698

Natural products play an important role in the discovery of new drugs, either by isolating novel structures or obtaining semi-synthetic ones. However, due to the complex nature, these studies are real challenges and require more modern approaches, such as the use of nuclear magnetic resonance techniques, more precisely, Ordered Diffusion Spectroscopy (DOSY) experiments. These assist in the elucidation of structures in a mixture, fractions of an extract; for example, and are also used in drug-receptor interaction studies. Thus, twenty derivatives were obtained, highlighting 3-oxo-N- (phenylalanine) -olean-18-en-28-amide (11), 3- oxo-N- (L-threophenylserine) -olean-18- en-28-amide (19) and 3-oxo-N- (D-threo - phenylserine) -olean-18-en-28-amide (20), all with carboxylic acid functional group present. In some cases derivative 20 was superior to the standard used, such as CLM for Staphylococcus aureus four times more efficient than standard, or MIC for Enterobacter aerogenes twice as large, or CLM for the same strain 64 times better. The same can be observed for derivative 19, compared to Salmonella typhimurium twice as active. With the studies of orderly diffusion it was possible to elucidate structures in a mixture, including a pair of diastereoisomers, proved the possibility of monitoring the metabolites and receptor complementations.