Indirubin is the known impurity from the commercial synthesis of indigo. Recent studies suggest that indirubin and its derivatives have potential to treat a wide variety of ailments such as cancer, diabetes and inflammation by acting as a kinase inhibitor which binds at the ATP site. However, limitations exist in its synthesis because it is typically produced by reacting indoxyl with isatin when following Baeyer's procedure from the 1880s. To extend low-cost access to a wide variety of indirubins, methodologies are being developed to alter the product preference. The recently published work from this lab suggests a condensation pathway leads to indirubin formation under appropriate conditions through an indoxyl intermediate. Current progress with this project will be presented in two key areas. First, computational studies have determined the relative abundance of keto and enol forms for a wide variety of indoles. Gaussian was used to calculate the relative enthalpies of various indoles to explore the kinetic components of the reaction. Second, mixed condensation reactions have helped assess the relative nucleophilicity and electrophilicity for a range of indoles under indoxyl-forming conditions.

Evaluating the mechanistic pathway of indirubin formation from an indoxyl intermediate

ACS Spring Meeting 2021

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