Reactivity of isatins with 2-aminonaphthoquinones promoted by barbituric acid and derivatives: synthesis and in silico evaluation of analogues of the pentacyclic alkaloid alpkinidine
Cascade reaction, isatin, 2-amino-naphthoquinone
In this work, the development and optimization of a new synthetic route were carried out to access analogous pentacycles of the alkaloid alpkinidine simply in a single step, without the need for the use of a column for purification or the use of metals as catalysts. Using ethanol, which is non-toxic and renewable, as a solvent. The use of microwaves allowed us to access the alpkinidine analogues containing the ABCD rings of the alkaloid in a reduced time and with moderate to good yields. Nine new analogues were synthesized using five-substituted isatins and N-substituted 2-amino-naphthoquinones as reagents and thiobarbituric acid as the promoter. An in-silico evaluation of the absorption, distribution, metabolism, excretion and toxicity (ADMET) properties of the synthesized analogues was also carried out.