The thyroid excretes tyrosine based hormones that have a pivotal role in organism development and metabolism. The principle thyroid hormone (TH) produced by the thyroid is thyroxin, which exists actively in vivo as the metabolic stimulator triiodothyronine. 3-iodothyronamine (T1AM) is a recently discovered derivative of TH that acts as a potent agonist of the trace amine associated receptor (TAAR), a subclass of the G-coupled protein receptor, but with inverse physiological effects of TH. Previous studies have shown T1AM evokes rapid biochemical responses in mice such as hypothermia and cardiac depression, demonstrating the possibility of a regulatory relationship between TH and T1AM. Further exploration of this regulatory mechanism encompasses the systematic examination of the chemical structure activity relationship of T1AM. Incorporation of a urea system in place of the ether linkage in T1AM has led to potent TAAR1 activation. The goal of this project is to expand on this structure activity relationship by specifically examining ortho substituted aromatic systems in addition to a urea linkage. Herein is reported progress towards the synthesis of a novel T1AM derivative N-[2-(2-aminoethyl) phenyl]-N'-phenyl urea as a principle compound for the generation of similar analogues.

Progress towards the synthesis of ortho substituted derivatives of T<sub>?1</sub>?AM as potent TAAR activators

247th National Meeting (2014)

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Progress towards the synthesis of ortho substituted derivatives of T?1?AM as potent TAAR activators

Progress towards the synthesis of ortho substituted derivatives of T_?1?AM as potent TAAR activators