Síntese de ácidos 2-arilquinolino-4-carboxílicos através da reação de Pfitzinger sob irradiação de micro-ondas

Abstract

Quinoline core is repeatedly found in many natural and synthetic products, including several important drugs that are used clinically, as well as pharmaceutical combinations. Within the important classes of quinolines, 2-aryl-4-carboxylic acids applications are most important which are due to their broad medicinal properties, such as antibacterial, antifungal, anthelmintic, antileishmanial, and antimalarial activity. Like these other essential actives, as precursors in the synthesis of other products, a search for a shorter time and more efficient synthesis is necessary. Therefore, the present work aims at the synthesis of 8 2-aryl-quinoline-4-carboxylic acids, having a new compound among these, through the Pfitzinger reaction, in basic medium, using heating and employing microwave irradiation. The acids were obtained with yields ranging from 48% to 98%, with reaction times from 5 to 15 minutes, and were characterized by carbon and hydrogen nuclear magnetic resonance (C-APT NMR and 1H NMR) and infrared spectroscopy. In silico studies were performed from all synthesized, which have been shown to have good oral bioavailability, without any violation of Lipinski's 5 parameters, which have no apparent oral toxicity. All synthesized in this work are going to biological activity tests.