SÍNTESE DE POTENCIAIS MARCADORES CELULARES A PARTIR DA REAÇÃO DE INDÓIS N-SUBSTITUÍDOS COM A 1,4-NAFTOQUINONA

Abstract

Indoles and quinones are classes of compounds that have been widely studied because they have different biological activities, such as antitumor, antidiabetic, and leishmanicidal activity, among others. The literature demonstrates that when these two classes of compounds react, the products formed continue to show biological activity and, in some cases, fluorescence. This characteristic is observed, for example, in polycyclic compounds containing heteroatoms, highly conjugated π systems and rigid structures. This work aims to synthesize fluorescent compounds through reactions between different indoles and 1,4-naphthoquinone and to evaluate their potential application as fluorescent probes in living cells. Several reactions were carried out to optimize the process of obtaining the derivatives, varying the solvent, molar equivalents of the reactants, temperature and reaction time. Using the best conditions, two derivatives were obtained in the coupling reaction of 1-methyl-1H-indole and 1,4-naphthoquinone in the presence of acetic acid as a solvent. The two compounds obtained had their spectroscopic properties in the UV/Vis region and fluorescence evaluated, and initial tests were also carried out for their application as labeling probes in live cells. In the current stage of the research, indoles are being prepared, already described in the literature, to be used later in the coupling reaction with 1,4-naphthoquinone, thus allowing the synthesis of new compounds. The experiments carried out and the vast applicability of these compounds encourage the continuity of research in the process of obtaining the derivatives.