INDOLE ADDITION TO BENZYLIC ALCOHOLS TO SYNTHESIZE PHENYL PHIDIANIDINE ANALOGS
Presentation Type
Event
Full Name of Faculty Mentor
Bryan Wakefield
Major
Biochemistry
Presentation Abstract
Alzheimer's disease impacts people around the world and reactive oxygen species (ROS) may accelerate the onset and progression of the condition. The phidianidines are natural products that have neurological activity with analogs of these compounds being able protect nerve cells from ROS damage. Our goal is to synthesize new analogs that can be tested to determine how specific structural changes impact the biological activity of these molecules. In particular, an analog that replaces the central 1,2,4-oxadizole ring with a simple phenyl ring was examined and two methods for addition of substituted indole rings were evaluated. First, a two-step process that replaced the alcohol with a halide or sulfonate leaving group followed by displacement with indole was attempted but provided low yields. Currently, direct addition of the indole to the benzylic alcohol using transition metal catalysts is being attempted. Once completed, these new analogs will be tested to determine their ability to prevent ROS damage.
External Presentation
1
Location
Lib Jackson Student Union, Atrium
Start Date
16-4-2019 12:30 PM
End Date
16-4-2019 2:30 PM
Disciplines
Biochemistry
Recommended Citation
Holt, Esther, "INDOLE ADDITION TO BENZYLIC ALCOHOLS TO SYNTHESIZE PHENYL PHIDIANIDINE ANALOGS" (2019). Undergraduate Research Competition. 26.
https://digitalcommons.coastal.edu/ugrc/2019/poster/26
INDOLE ADDITION TO BENZYLIC ALCOHOLS TO SYNTHESIZE PHENYL PHIDIANIDINE ANALOGS
Lib Jackson Student Union, Atrium
Alzheimer's disease impacts people around the world and reactive oxygen species (ROS) may accelerate the onset and progression of the condition. The phidianidines are natural products that have neurological activity with analogs of these compounds being able protect nerve cells from ROS damage. Our goal is to synthesize new analogs that can be tested to determine how specific structural changes impact the biological activity of these molecules. In particular, an analog that replaces the central 1,2,4-oxadizole ring with a simple phenyl ring was examined and two methods for addition of substituted indole rings were evaluated. First, a two-step process that replaced the alcohol with a halide or sulfonate leaving group followed by displacement with indole was attempted but provided low yields. Currently, direct addition of the indole to the benzylic alcohol using transition metal catalysts is being attempted. Once completed, these new analogs will be tested to determine their ability to prevent ROS damage.