Síntese e atividade toxicológica de (3-fenil-1,2,4-oxadiazol-5-il) metanol.

Abstract

The (re)emergence of new pathogenic agents, over the decades, has been boosting the Research, Development and Innovation (R,D&I) of pharmaceuticals. Among the numerous classes of organic molecules, 1,2,4-oxadiazoles deserve special attention, in part, due to their broad spectrum of biological activities and their presence in several medications available on the market. Additionally, 1,2,4-oxadiazoles have been explored as pesticides, larvicides and technological materials (OLED screens). Therefore, the objective of the work was to synthesize benzamidoxime, ethyl glycolate and (3-phenyl-1,2,4-oxadiazole-5-yl) methanol, as well as evaluate the toxicity of (3- phenyl-1, 2,4-oxadiazole-5-yl) methanol. Benzamidoxime was prepared from the reaction between benzonitrile and hydroxylamine hydrochloride in a hydroethanolic medium in a basic medium, while ethyl glycolate through the esterification reaction in an acidic medium of glycolic acid and ethanol. (3-phenyl-1,2,4-oxadiazole-5-yl) methanol was synthesized from the reaction between benzamidoxime and ethyl glycolate using a super basic medium (DMSO+NaOH). The characterization of benzamidoxime, ethyl glycolate and (3-phenyl-1,2,4-oxadiazol-5-yl) methanol was

carried out using spectroscopic techniques. The toxicological biassay of (3-phenyl- 1,2,4-oxadiazole-5-yl) methanol was carried out using Artemia salina larvae. As

results, benzamidoxime and ethyl glycolate were obtained in yields of 72% and 74%, respectively, while (3-phenyl-1,2,4-oxadiazole-5-yl) methanol was obtained in 56% yield. Benzamidoxime, ethyl glycolate and (3-phenyl-1,2,4-oxadiazole-5-yl) methanol were characterized by IR, 1H NMR and 13C NMR, in which the wave numbers and chemical shifts obtained prove that they have been obtained. Finally, toxicological bioassays on Artemia salina resulted in an LC50 of 172.23 μg/mL for (3-phenyl-1,2,4- oxadiazole-5-yl) methanol, indicating that this compound has moderate toxicity. In

short, these results encourage future research involving (3-phenyl-1,2,4-oxadiazole- 5-yl) methanol, especially regarding its mechanism of action.