Glicosídeo 2,3 - insaturado: síntese, caracterização estudo farmacológico e toxicológico in vitro e in silico.

Abstract

Medicines and pharmaceutical technologies play a key role in global health, so its development and discovery process is widely needed. In this context, a class of molecules that has been attracting the scientific community are the 2,3-unsaturated O-glycosides, simple molecules, derived from natural sources with interesting biological activities. Thus, the objective of this work was to synthesis of iso-propyl 4,6-di-O-acetyl-2,3-dideoxy-á-D-erythro-hex-2-enopyranoside, evaluation of its toxicity to Artemia salina Leach and the theoretical study of their pharmacodynamic, pharmacokinetic and toxicological properties from different in silico methods. This 2,3-unsaturated O-glycoside was obtained in 91% yield after 30 minutes of reaction and was further characterized. The evaluation of the toxicity to Artemia salina resulted in a LC50 of 779,503 ìg/mL in the range of 683,246 to 883,730 ìg / mL, classified as slightly toxic, a very promising result. The in silico methods indicated that the molecule has a low probability of presenting toxic effects, good characteristics to become a good drug, an excellent oral bioavailability potential, and the probability of performing different functions by different pharmacological mechanisms, highlighting the actions antineoplastic, antibiotic, antiallergic, enzymatic inhibition, among others. In summary, iso-propyl 4,6-di-O-acetyl-2,3-dideoxy-á-D-erythro-hex-2-enopyranoside has a proven probability of triggering different physiological effects, being able to act by different routes with low risk of toxic effects and the possibility of oral administration. In addition, this molecule can be easily prepared and presented low toxicity to Artemia salina, which motivates the experimental studies of the activities of the same as its derivatives.