Abstract
The synthesis of the heterocyclic food mutagen, 2-amino-1-methyl-6-phenylimidazo[4,5b]pyridine (PhIP) 7, is reported. PhIP 7 was synthesized in six steps from commercially available 2,3-diaminopyridine 1 in 6% overall yield. This route features a new ring closure reagent, Ndichloromethylene-p-toluenesulfonamide, to assemble the imidazo[4,5-b]pyridine ring system and uses a Suzuki coupling to introduce an aryl ring onto the heterocyclic core as the last synthetic step.
Highlights
Diet is one of the most significant environmental causes of cancer in humans.[1]
The most mass abundant of the heterocyclic amines is 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) 7.1 PhIP 7 forms covalent DNA adducts resulting in genetic mutations in animal and human models.[4]
In our continued effort to develop new methods for the syntheses of biologically important mutagens and carcinogens, we report a new method for the synthesis of 7
Summary
Diet is one of the most significant environmental causes of cancer in humans.[1]. A series of mutagenic and carcinogenic heterocyclic amines has been identified from cooked meat and fish.[2].
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