Síntese e avaliação antituberculose de novos compostos organosselenio

Abstract

Tuberculosis has Mycobacterium tuberculosis as its etiologic agent. It is among the 10 causes of death in the world, according to the World Health Organization (WHO), this is due to late diagnosis, which triggers inappropriate treatment, either by the delay in confirming the disease, inappropriate administration of effective drugs or the lack of adequate treatment. treatment adherence, all this leads to the evolution of strains resistant to existing drugs. Organoselenium compounds have been highlighted by their applicability in biological studies, showing antimicrobial, anti-inflammatory, antinociceptive, anticancer activities, among others. Thus, the present study aimed to prepare new molecules of selenorganics containing aromatic rings, aiming to obtain molecules with useful biological potential characterized as antimicrobial and to establish the structure-activity relationship of the substances evaluated. The compounds were synthesized using the methodology of Souza et al., (2019) and the compounds were characterized by the spectroscopic techniques of Infrared, 1H and 13C Nuclear Magnetic Resonance and presented yields ranging from 53 – 75.6%. Among the twenty-four substances obtained, twelve are unpublished in the literature. In the antituberculosis activity test, the determination of the minimum inhibitory concentration (MIC) was performed. Through the results obtained, it can be observed that all compounds demonstrated an antituberculosis effect against the Mycobacterium tuberculosis strain. The compounds MSe4, MSe3, MSe6 and MSe7 showed better activity with MIC value = 20.67; 21.6; 22.04 and 22.52 μg/mL, respectively. As for the structural characteristics of the compounds on the antituberculosis bioactivity, the importance of minor carbon chains and substituent groups was evidenced. The molecular docking study suggested that it is the oxygen and hydrogen atoms of the methoxy group, carbons of the benzene ring, oxygen atoms of the carbonyl and epoxide ring present in the structure, responsible for the interactions with enzymatic residues, being therefore important for the activity of the selenium compounds under study.