Presentation Type
Poster
Full Name of Faculty Mentor
Bryan Wakefield, Chemistry
Major
Biochemistry
Presentation Abstract
Phidianidines are natural products originally isolated from Phidiana Militaru, a shell-less mollusk. The compounds are comprised of an indole, a 1,2,4 oxadiazole ring, and an aminoalkylguanadine group on the C-3' position of the ring. They have been found to neutralize reactive oxygen species and are agonists of the µ-opioid receptor. Other groups have synthesized analogues of the phidianidines that have substituted the aminoalkylguanadine group for a biaryl ring system, which has been shown to have neuroprotective properties. The current synthetic routes make substitution of the indole and changing the oxadiazole difficult, so our goal is to create a synthesis that allows for variations of these groups to determine the impacts on the biological activity. Our approach to these analogues hinges on the addition indole to an aromatic aldehyde. We are using simple aldehydes to identify reaction conditions that can then be used to complete the synthesis.
Location
Poster Session 1
Start Date
12-4-2022 12:30 PM
End Date
12-4-2022 2:30 PM
Disciplines
Chemistry
Recommended Citation
Newton, Lindsay and Tingler, Anna, "Identifying Conditions for Indole Additions to Aldehydes to be Applied to the Synthesis of Phidianidine Analogues" (2022). Undergraduate Research Competition. 55.
https://digitalcommons.coastal.edu/ugrc/2022/fullconference/55
Included in
Identifying Conditions for Indole Additions to Aldehydes to be Applied to the Synthesis of Phidianidine Analogues
Poster Session 1
Phidianidines are natural products originally isolated from Phidiana Militaru, a shell-less mollusk. The compounds are comprised of an indole, a 1,2,4 oxadiazole ring, and an aminoalkylguanadine group on the C-3' position of the ring. They have been found to neutralize reactive oxygen species and are agonists of the µ-opioid receptor. Other groups have synthesized analogues of the phidianidines that have substituted the aminoalkylguanadine group for a biaryl ring system, which has been shown to have neuroprotective properties. The current synthetic routes make substitution of the indole and changing the oxadiazole difficult, so our goal is to create a synthesis that allows for variations of these groups to determine the impacts on the biological activity. Our approach to these analogues hinges on the addition indole to an aromatic aldehyde. We are using simple aldehydes to identify reaction conditions that can then be used to complete the synthesis.