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RESVERAMORPHS AS PROTECTIVE AGENTS AGAINST EPILEPSY: OPTIMIZATION OF REDUCTIVE ALDOL BICYCLIZATION AND ANALOG SYNTHESIS WITH FUNCTIONAL GROUP VARIATION TO ASSESS IMPACT ON BIOACTIVITY

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Date Issued:
2023
Abstract/Description:
This work encompasses the synthesis, analysis, and optimization of [3.2.1] all-carbon bridged bicyclic compounds, known as resveramorphs (RVM), Studies were conducted using a Caenorhabditis elegans model, where RVMs were tested for antiseizure capabilities. In both applications, RVMs proved potent with activities in the sub-nanomolar level in one case. A structure-activity relationship (SAR) was hypothesized for the identification of the pharmacophore. The six to seven step synthesis route towards the RVM analogues is discussed in further detail. The bicyclization of the RVMs is achieved through a reductive aldol reaction. The reaction suffers from selectivity issues leading to multiple bicyclic products. By following a one-factor-at-a-time (OFAT) methodology, attempts at optimization for this reaction were made, however, despite important gains, the overall yields of the bicyclic product remain low. Other products from this reaction have been used to understand the reaction mechanism, which will be the basis for future efforts to further optimize this key step.
Title: RESVERAMORPHS AS PROTECTIVE AGENTS AGAINST EPILEPSY: OPTIMIZATION OF REDUCTIVE ALDOL BICYCLIZATION AND ANALOG SYNTHESIS WITH FUNCTIONAL GROUP VARIATION TO ASSESS IMPACT ON BIOACTIVITY.
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Name(s): Jutte, Elyse M. , author
Lepore, Salvatore D. , Thesis advisor
Florida Atlantic University, Degree grantor
Department of Chemistry and Biochemistry
Charles E. Schmidt College of Science
Type of Resource: text
Genre: Electronic Thesis Or Dissertation
Date Created: 2023
Date Issued: 2023
Publisher: Florida Atlantic University
Place of Publication: Boca Raton, Fla.
Physical Form: application/pdf
Extent: 104 p.
Language(s): English
Abstract/Description: This work encompasses the synthesis, analysis, and optimization of [3.2.1] all-carbon bridged bicyclic compounds, known as resveramorphs (RVM), Studies were conducted using a Caenorhabditis elegans model, where RVMs were tested for antiseizure capabilities. In both applications, RVMs proved potent with activities in the sub-nanomolar level in one case. A structure-activity relationship (SAR) was hypothesized for the identification of the pharmacophore. The six to seven step synthesis route towards the RVM analogues is discussed in further detail. The bicyclization of the RVMs is achieved through a reductive aldol reaction. The reaction suffers from selectivity issues leading to multiple bicyclic products. By following a one-factor-at-a-time (OFAT) methodology, attempts at optimization for this reaction were made, however, despite important gains, the overall yields of the bicyclic product remain low. Other products from this reaction have been used to understand the reaction mechanism, which will be the basis for future efforts to further optimize this key step.
Identifier: FA00014288 (IID)
Degree granted: Thesis (MS)--Florida Atlantic University, 2023.
Collection: FAU Electronic Theses and Dissertations Collection
Note(s): Includes bibliography.
Subject(s): Epilepsy--Animal models
Bridged Bicyclo Compounds
Resveratrol
Persistent Link to This Record: http://purl.flvc.org/fau/fd/FA00014288
Use and Reproduction: Copyright © is held by the author with permission granted to Florida Atlantic University to digitize, archive and distribute this item for non-profit research and educational purposes. Any reuse of this item in excess of fair use or other copyright exemptions requires permission of the copyright holder.
Host Institution: FAU