Michael Kienzler, William Gramlich
Matthew Brichacek, Margaret Killinger, Natalie Machamer
Serotonin has various functions throughout the body and directly effects many neurological diseases/disorders, like depression, that are linked to the dysregulation of serotonin. Triptans are indole containing drugs that bind to a subset of serotonin receptors (5-HT1Band 5-HT1D) and are used to treat migraines. In this project, the synthesis of anindole intermediate is attempted. Ideally, an azobenzene would have been added to the 5th position (replacing the primary amine). Azobenzenes are compounds composed of 2 benzene rings connected by a nitrogen-nitrogen double bond that can switch between cis and trans conformations by absorbing different wavelengths of light. The transformation of the indole intermediate into a photoswitch is believed to be possible based on the structures of triptans.The first two steps of the synthesis of the indole intermediate were completed and product was produced with 72.9% yield. The column conditions that provided the best separation was determined to be 5% methanol in DCM with triethylamine. The reaction stopped working due to age and instability of the reagents.
Sainsbury, Chelsea, "The Synthesis of Photoswitchable Triptan Derivatives" (2021). Honors College. 683.