Cholesterol and cholestanediol were converted into nitrogen-substituted cholesterol derivatives using several methods with varying degrees of success. The methodologies included Mitsunobu-type reaction, oxidation, imine-formation and imine reduction. Successful reactions resulted in cholesterol derivatives with nitrogen bearing nucleophilic substrates replacing the original alcohol substituents. Infrared and NMR spectroscopy studies confirmed the success of these reactions. In the IR, disappearance of the O-H band and appearance of N-H and N-C absorbance bands support transformation. Additional evidence supporting substitution of the alcohol with the nitrogen bearing nucleophilic substrates came from a distinct shift in the alpha-hydrogen NMR signal. The chemical shift of the alpha-hydrogen on the cholesterol starting material is 3.54 ppm. Reactions using aniline and sodium azide, for example, resulted in a 0.2 to 0.3 ppm shift from the original. Future work will use the <i>N</i>-substituted derivatives synthesized in the development of a metal complex-based cholesterol-derived tetraazamacrocycle which can potentially serve as an anticancer agent and cancer diagnostic agent.

Synthesis of amine functionalized cholesterol derivatives for use in metal-complex based imaging agents

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