- Synthesis and mutagenic potency of structural isomers of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine
-
(Chemical Equation Presented) Synthesis of 2-amino-1-methyl-6- phenylimidazo[4,5-b]pyridine (PhIP), three structural isomers, and two desphenyl PhIP congeners has been carried out. Mutagenic potency was evaluated using S. typhimurium strain TA98 in the Ames test. Mutagenic potency increased in relation to structural features in these heterocyclic amines that allow extended resonance between the phenyl and imidazo[4,5-b]pyridine N2-amino substituents. By contrast, PhIP isomers, whose substitution disallows involvement of the phenyl group in their ammoimidazo resonance hybrids, and desphenyl congeners were from 86- to 234-fold less mutagenic than PhIP.
- Chrisman,Knize,Tanga
-
experimental part
p. 1641 - 1649
(2009/08/09)
-
- An easy photochemical approach to the synthesis of the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine
-
Mutations induced by substances formed during food cooking are a field of growing interest; for a better comprehension of the mechanism of action of these carcinogens, simple routes to their synthesis are needed. In this letter we describe an easy method for 2-amino-1-methyl-6-phenylimidazo[4,5- b]pyridine (PhIP) synthesis, starling from the commercially available 2,3- diaminopyridine 1 via the 2-amino-3-methylamino-5-phenylpyridine 5 formation. The key step of this approach is the one pot synthesis of 5 performed by photolysis of 2-amino-5-iodo-3-(N-methyl-N-tosylamino)pyridine 4 to obtain simultaneous phenylation and tosyl group removal. Compound 5 was then used as an intermediate to obtain the 1-methyl 6-phenylimidazo[4,5-b]pylidine 6 which was aminated to afford PhIP in good overall yields.
- Bavetta, Fabio S.,Caronna, Tullio,Pregnolato, Massimo,Terreni, Marco
-
p. 7793 - 7796
(2007/10/03)
-
- THE SYNTHESIS OF THE COOKED-BEEF MUTAGEN 2-AMINO-1-METHYL-6-PHENYLIMIDAZOPYRIDINE AND ITS 3-METHYL ISOMER
-
2-Amino-1-methyl-6-phenylimidazopyridine, a mutagenic compound newly isolated from cooked beef, and its 3-methyl isomer have been synthesized.The spectroscopic data and the mutagenicity of the isomers are compared.
- Knize, Mark G.,Felton, James S.
-
p. 1815 - 1819
(2007/10/02)
-