Azo compounds contain a nitrogen-nitrogen double bond. Drugs with this group are known to be photo-switchable, with the compound changing from the <i>trans</i> conformation to the c<i>is</i> conformation (and vice versa) when irradiated with a specific wavelength of light. Given that a drug’s shape is critical for its effectiveness, changes in a molecule’s conformation translate to changes in its bioactivity. This property can be harnessed to make drugs which can be activated in a location-specific manner. By activating the drug in a location-specific manner, we reduce the potential for side effects that are caused by drugs acting in undesired locations. Although such drugs are becoming more prevalent, all current examples are based on azo-benzene. Azo-indole compounds are particularly interesting as drugs given the prevalence of indole motifs in drug molecules. However, synthetic methods for creating drug-like azo-indoles are far less established. We have therefore set out to develop new methods for synthesizing such compounds, with efforts focused on the addition of indole to various diazonium salts to create azo-indoles. This presentation will focus on the synthetic challenges associated with these particular molecules, as well as advances in their synthesis.

Examining methods for the synthesis of azo-indole compounds

2019 Fall National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.