Date of Award

5-2012

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Keith Kyler, Ph.D.

Second Advisor

Anne E. Kondo, Ph.D.

Third Advisor

Carl LeBlond, Ph.D.

Fourth Advisor

Jonathan Southard, Ph.D.

Abstract

The objective of this research was to synthesize therapeutic agents that could specifically inhibit the type II isoform of inosine monophosphate dehydrogenase (IMPDH). In preparing for the synthesis of 6-alkoxycarbonyl-3-ethyl-3-phenyl-1,5-diazabicyclo[3.1.0]hexane 2,4-dione (1) this research successfully synthesized diethyl phenyl malonate, ethyl dibromoaceate, and 4-ethyl-4-phenylpyrazolidine-3,5-dione. Additionally, ethyl bromo (4-ethyl-3,5-dioxo-4-phenylyrazolidin-1-yl)acetate was successfully synthesized via a pathway involving alkylation of 4-ethyl-4-phenylpyrazolidine-3,5-dione with ethyl dibromoaceate. While, there was no success in synthesizing 6-alkoxycarbonyl-3-ethyl-3-phenyl-1,5-diazabicyclo[3.1.0]hexane 2,4-dione; however, a number of additional compounds, including 2,6-diethyl-2,6-diphenyl-1H,5H-pyrazolo[1,2-a]pyrazole-1,3,5,7(2H,6H)-tetrone, were afforded via these.

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