Date of Award

Summer 8-10-2022

Degree Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Binghe Wang

Abstract

Carbon monoxide (CO) is an important endogenous signaling molecule that has pleiotropic effects through the regulation of a series of hemoprotein targets. It has been demonstrated repeatedly that there is a need for organic CO donors of various properties capable of the controlled release of CO since inhalation delivery has safety concerns and the reactivity and toxicity of metal-based donors are un-resolved issues. Our research group has previously described the synthesis and kinetic studies of organic CO prodrugs of various types with tunable release rates. In one series, the design makes use of an inverse-electron demand Diels-Alder cycloaddition, followed by a cheletropic reaction of the resulting norbornadienone intermediate to release CO. Herein, we describe the synthesis, characterization, and release kinetics of analogous CO prodrugs, with the aim of improved structural properties and/or release kinetics. These new CO prodrugs will add to the diverse set of CO donors available.

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