Aromatic fluorination is a remarkably successful and seemingly general technique by which medicinal chemists can modulate and control the catabolism of pharmaceuticals. The reason why this approach works in medicinal chemistry can be traced directly to the atomic properties of the fluorine atom. Aromatic fluorine substitution is unique in that it provides a small, non-labile substituent without altering the aromatic properties that are most important for target binding. The origins of the particular suitability of specific arene substitution patterns will also be highlighted.For the same reasons that fluorine substitution finds utility in drug design, F18 substitution is a potentially general approach to access a large number of new radiotracers for PET imaging development. Unfortunately, much of the �cold� synthetic chemistry used to introduce fluorine (F19) into compounds cannot be used to introduce the �hot� label, F18. The second portion of the talk will discuss the development of a general methodology to synthesize 18F-labeled aromatic amino acid derivatives with cyclotron-derived, no-carrier-added F18-fluoride. Examples of compounds prepared using this technique are F18-6-fluoro-L-DOPA and F18-6-fluorodopamine. Initial imaging studies with these compounds will be presented.

Fluorination in pharmaceutical and imaging applications

245th National Meeting (2013)

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