SYNTHESIS OF FERROCENE-OXADIAZOLE COMPLEXES AND A DETERMINATION OF THEIR LogD VALUES
Author: Grace C. Gould
Graduation Year: 2016
Thesis Advisor: Alice E. Bruce
Description of Publication: During the drug design process, there are many different approaches that researchers can take to improve the overall efficacy of a potential drug candidate. Aside from attempting to understand how different functional groups interact with target tissues, the physical properties of a particular molecule are also important determinants of overall effectiveness. If a molecule is too polar, it will display low permeability through the gastrointestinal tract, and will most likely be excreted through the body unchanged. Conversely, if a molecule is too nonpolar, it will be insoluble in blood and will display low distribution throughout tissues. This research describes attempts at the synthesis of multiple ferrocene-oxadiazole complexes, with an effort towards synthesizing compounds which display an aqueous solubility similar to candidates currently used in drug design. Oxadiazoles are a class of 5-membered, heterocyclic molecules which have attracted a tremendous amount of attention in recent years for their vast array of medicinal properties. Furthermore, the conjugation of ferrocene to bioactive molecules has demonstrated involvement with the suppression of cancer cells in mice. In this project, the aqueous solubility of one such ferrocene-oxadiazole complex was estimated using the LogD shake-flask assay, resulting in a value of 1.21. The results of an attempted synthesis of a more hydrophobic ferrocene-oxadiazole complex will be explained as well, along with a discussion of the challenges associated with different synthetic methods.
Location of Publication:
URL to Thesis: https://digitalcommons.library.umaine.edu/honors/385