Document Type
Dissertation
Degree
Doctor of Philosophy (PhD)
Major/Program
Chemistry
First Advisor's Name
Kathleen S. Rein
First Advisor's Committee Title
Committee Chair
Second Advisor's Name
Stanislaw Wnuk
Third Advisor's Name
Philip Stoddard
Fourth Advisor's Name
Fenfei Leng
Fifth Advisor's Name
John T. Landrum
Date of Defense
7-17-2006
Abstract
The kainoids are a class of non-proteinogenic pyrrolidine dicarboxylates that exhibit both excitatory and excitotoxic activities. These activities are a result of the ability of the kainoids to act as glutamate receptor agonists by activating ionotropic glutamate receptors. The parent of this group of compounds is x-kainic acid. Kainic acid is isolated from the seaweed Diginea simplex and has been used in Asian countries as a treatment for intestinal worms in children. In addition it is used extensively by neuropharmacologists for the study of glutamate receptors. Several years ago, the world's sole supplier of kainic acid discontinued this product. Since that time, other sources have appeared, however, the price of kainic acid remains significantly higher than it once was. We have thus been working on synthesizing aza analogs of kainoids which would be less costly but potentially potent alternatives to kainic acid via the dipolar cycloadditions of diazoalkanes with trans diethyl glutaconate. These 1, 3-dipolar cycloadditions yielded 2- pyrazolines or pyrazoles. The 2-pyrazolines may be precursors to aza analogs of kainoids. The regioselectivity of these 1, 3-dipolar cycloadditions and isomerization of the 1- pyrazolines to 2-pyrazolines was evaluated. Reductions of the 2-pyrazolines yielded aza analogs of kainoids.
Identifier
FI14062265
Recommended Citation
Di, Mingping, "Syntheses of aza analogs of kainoids" (2006). FIU Electronic Theses and Dissertations. 2795.
https://digitalcommons.fiu.edu/etd/2795
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