News & Events
Dr. Herman Holt Jr.
Posted on February 13, 2015
Date - February 13, 2015
1:00 pm - 2:00 pm
Associate Professor of Chemistry
Chair, Department of Chemistry
“Synthesis of Heterocyclic Combretastatin and Chalcone Molecules”
Our group has set out to prepare indole analogues of combretastatin A-4 (CA-4) and chalcones. Both CA-4 and some chalcones are effective tubulin binding agents which ultimately disrupts vascular function. The Hemetsberger-Knittel method was used to successfully prepare substituted indoles from α-azidocinnamates in good yields. Oxidation state adjustment generated a highly diverse indole aldehyde that can be used in a variety of ways. One carbon homologation provided ethynyl indoles as functional dipolarophiles in catalyzed 1,3-dipolar cycloadditions to produce a 2-(1,2,3-triazolyl)indole. In addition, the synthesis of indole chalcone and α-halo substituted indole analogs of CA-4 can be performed. The synthesis of some indole aldehydes and their utility will be described in the seminar.