Polyacetylene glycosides (PAGs) constitute a relatively small class of secondary metabolites characterized by the presence of a sugar unit anomerically connected to a polyacetylene. These compounds are found in fungi, seaweed, and more often in plants. PAGs exhibit a wide range of biological and pharmacological activities and, as a result, the literature of these compounds has grown exponentially in recent years.
Os O-glicosídeos são carboidratos de ocorrência natural e que apresentam atividades biológicas promissoras. No entanto, o caminho convencional para comercialização de um medicamento envolve um processo exaustivo e caro. Em contrapartida, pesquisas baseadas em uma abordagem in silico, têm se mostrado eficientes na predição de propriedades farmacodinâmicas, reduzindo tempo e custos. Nesse trabalho, relatamos a síntese, assinalamento completo e avaliação do perfil farmacocinético e de toxicidade do 2-propin-1-il 2,3,4,6-tetra-O-acetil-β-D-glicopiranose. O composto foi obtido em bom rendimento e excelente estereosseletividade. A partir do experimento de NOESY foi possível determinar o produto majoritário da reação de glicosilação. O estudo in silico, relatado pela primeira vez, indicou que este composto apresenta boa biodisponibilidade oral, é ativo frente aos principais alvos moleculares e exibe baixa toxicidade.
The development of chemotherapy agents without side effects is a major challenge, since traditional medicines usually have undesirable properties such as high toxicity, resistance and low bioavailability. In this sense, computational methods play a crucial role in the discovery and optimization of new drugs, as they combine speed and efficiency with low cost. The 1,2,4-oxadiazoles are one of the main classes of heterocyclics due to their numerous biological applications. In this work, we report the synthesis, antineoplastic evaluation and in silico study of a new 1,2,4-oxadiazole. The (S)-N-(1-hydroxy-3-methylbutan-2-yl)-3-(p-toluyl)-1,2,4-oxadiazole-5-carboxamide was obtained after two reaction steps in excellent yield. Although it has shown low activity in relation to the MCF-7, HCT116 and HL60 tumor cell lines, the molecular docking study indicates that this compound acts in the colchicine site and can inhibit tubulin polymerization. From the calculation of pharmacokinetic properties by the SwissADME and Osiris Property Explorer programs, it is possible to infer that the compound meets the Lipinski rules presenting good oral bioavailability and low toxicity.
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