Document Type



Doctor of Philosophy



First Adviser

Heindel, Ned

Other advisers/committee members

Schray, Keith J., Hazeyama, Yuji, Woo, David


The design and synthesis of tumor-seeking radiopharmaceuticals for detecting malignancy requires the solution to two problems: 1) selection of a "carrier group" with demonstrated specificity for the target to be imaged, and 2) selection of a way to attach the nuclide to that carrier. The psoralens, natural products well-established as malanizing agents, are known to be selectively incorporated into functioning melanocytes. Psoralens are the candidate agents for conversion into melanoma-localizing radiopharmaceuticals. This dissertation reports the development of several pre-labeling candidates for melanoma impacting. A facile new labeling method, the triazene decomposition, has been studied, its generality probed, its sensitivity to molecular substituent effects evaluated, and its applicability to other pharmaceutical classes tested. The triazene intermediates required for this labeling method have been examined for biological activity, for chemical stability, and for sensitivity of ring positions to transmission of electronic effects as measured by C-13 NMR. The triazene labeling method requires amino-bearing precursors. As a means to simple, non-pressurized reduction of nitro groups to amines to generate these necessary precursors, a palladium-catalyzed hydrogen transfer reaction with cyclohexene as the donor has proven extraordinarily useful.

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