Reatividade de isatinas com 2-aminonaftoquinonas promovida por ácido barbitúrico e derivados: síntese e avaliação in silico de análogos do alcaloide pentacíclico alpkinidina.

Abstract

In this work, we developed and optimized a new synthetic route to access analogs of the pentacyclic alkaloid alpkinidine in a simple, one-step process. This method does not require column purification or the use of metal catalysts. The application of microwave irradiation allowed us to synthesise alpkinidine analogues containing the ABCD rings more quickly, with yields ranging from 23% to 89%. These are considered good yields given the structural complexity of the compounds. Nine new, previously unreported analogs were synthesized using 5-substituted isatins and N-substituted 2-amino-naphthoquinones as reagents, with thiobarbituric acid serving as the promoter. Additionally, we performed an in silico evaluation of the absorption, distribution, metabolism, excretion, and toxicity (ADMET) properties of the synthesized analogs.