2- Phenylimidazo pyridine

Figure 11.4. Structures of various heterocyclic amines. IQ is 2-amino-3-methylimidazo-quinoline. MelQx is 2-amino-3,8-dimethylLtnidazo-quinoxalme. 4,8-DiMelQx is 2-amino-3,4,8-trimethylimidazo-quinoxaline. PhIP is 2-amino-l-methyl-6-phenylimidazo-pyridine. These and other related compounds can be found in fried or broil beef, fish, and chicken, but can also be created by cooking mixtures of creatinine, amino acids, and glucose. Microwave cooking, or cooking in aluminum foil, reduces the formation of heterocyclic amines. (From Sugimura, 1997.)...

A useful method of synthesis of 5-bromo- and 5,8-dibromo-3-methoxy-2-phenylimidazo[ 1,2-a]pyridines has involved quenching the lithium derivatives with bromine (83S987). 

An effective synthesis of the pyrido[T,2 l,2]imidazoI5,4-c]isoquinoline system 41 uses the 3-aceta (or benza)mido-2-phenylimidazo[l,2-a]pyridine 40 and phosphorus oxychloride. An alternative approach using the carbodiimide 42, obtained from the corresponding iminophosph(Mane and an isocyanate, is also successful <95H(41)2019>. 

NAGAO M (1995) Specific 5 -GGGA-3 - 5 -GGA-3 mutation of the Ape gene in rat colon tumours induced by 2-amino-1 -methyl-6-phenylimidazo [4,5-b]pyridine , Proc Nat Acad Sci, 92 910-14. 

HUBER W W, MCDANIEL L P, KADERLIK K R, TEITEL C H, LANG N P and KADLUBAR F F (1997) Chemoprotection against the formation of colon DNA adducts from the food-bome carcinogen 2-amino-l-methyl-6-phenylimidazo[4,5-b]pyridine (PhlP) in the rat , Mutat Res, 376 115-22. 

Aoki, H. et al., Inhibitory effect of anthocyanin colors on mutagenicity induced by 2-amino-l-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), Foods Food Ingred. J. Jpn., 209, 240, 2004. 

P. Pavek, G. Merino, E. Wagenaar, E. Bolscher, M. Novotna, J.W. Jonker, and A.H. Schinkel. Human breast cancer resistance protein Interactions with steroid drugs, hormones, the dietary carcinogen 2-amino-l-methyl-6-phenylimidazo(4,5-b)pyridine, and transport of cimetidine. J Pharmacol Exp Ther. 312 144—152... 

Figure 13.8 Mutagenic and carcinogenic heterocyclic amines (a) IQ (2-amino-3-methylimidazo[4,5-/ quinoline), (b) IQx (2-amino-3-methylimidazo[4,5-/ quinoxaline), (c) PhIP, (2-amino-l-methyl-6-phenylimidazo[4,5- ] pyridine), (d) 1,5,6-TMIP (2-amino-l,5,6-trimethylimidazo[4,5-6] p5ridine).

Y. Ueyama, Y. Monden, X. B. He, C. X. Lin, M. A. Momen, S. Mimura and A. Umemoto, Effects of bile acids on 2-amino-1-methyl-6-phenylimidazo-[4,5-b]pyridine-induced aberrant crypt foci and DNA adduct formation in the rat colon, J. Exp. Clin. Cancer Res., 2002, 21, 577. 

Z-aminO 1 -methy 1 6 phenylimidazo [4,5-b]-pyridine 2 aminO 3,7,8 trimethylimidazo[4,5 f]quinoxaline 2 aminO 3,4,7,8 tetramethyl 3H imidazO [4,5 f]quinoxaline inoxaline 3 aminO l,4 dimethyl SH pyrid [4,3 b] indole (Trp P I) and 3 aminO l methyl 5H pyrido [4,3 b]indole induced mutagenesis. Metabolic activation was required for positive results b... 

Amino-2-methylanthraquinone 2-Amino-3-methylimidazo[4,5-/]quinoline (see IQ) 2-Amino-6-methyldipyrido[l,2-a 3, 2 -fil]imidazole (see Glu-P-1) 2-Amino-l-methyl-6-phenylimidazo[4,5-6]pyridine (see PhIP)... 

Further styryl derivatives of 2-phenylimidazo[l,2-a] and of 2-phenyl-j-triazolo[l,5-a]pyridine are listed in Table XVI. 

On being heated with 5" aqueous alkali, 3-bromo-2-phenyl-4-oxo-4//-pyrido[l,2-a]pyrimidine was transformed to 2-phenylimidazo[l,2-u]pyri-dine, whereas the 2-methyl analog in 7"0 aqueous potassium hydroxide yielded a mixture of the 3-unsubstituted- and 3-carboxy-2-methylimidazo-[l,2-u]pyridines. Under similar conditions, 3-bromo-2-chloro- and 3-bromo-4-oxo-4ff-pyrido[l,2-a]pyrimidines decomposed to 2-aminopyridine.294... 

Boyce A, Doehmer J, Gooderham NJ. 2004. Phytoalexin resveratrol attenuates the mutagenicity of the heterocyclic amines 2-amino-l-methyl-6-phenylimidazo [4,5-b]pyridine and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline. J Chromatogr B Analyt Technol Biomed Life Sci 802 217-223. 

The nitration of l-phenylimidazo[l,5-a]pyridine (43) as the free base using nitric acid in acetic acid gives either the 3-mononitro or the 3-nitro-l-(4-nitrophenyl) dinitro product. 3-MethyI-l-phenylimidazo[l,5-u]-pyridine (as the hydrogen sulfate salt) gives the 4-nitrophenyl mononitro product, and a similar reaction of 3-phenylimidazo[l,5-a]pyridine gives the 1-nitro product [80JCS(P 1)959],... 

Frandsen H, Alexander J (2000) N-Acetyltransferase-dependant activation of 2-hydroxyamino-l-methyl-6-phenylimidazo[4,5-b]pyridine formation of 2-amino-l-methyl-6-(5-hydroxy)phenylimidazo[4,5-b]pyridine, a possible biomarker for the reactive dose of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Carcinogenesis 21 1197-1203... 

Kobayashi, M., Hanaoka, T., et al. 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) level in human hair as biomarkers for dietary grilled/stir-fried meat and fish intake. Mutat. Res. 588(2), 136-142, 2005. 

Strickland, P. T., Qian, Z., Friesen, M. D., Rothman, N., and Sinha, R. Metabolites of 2-amino-l-methyl-6-phenylimidazo(4,5,-b)pyridine (PhIP) in human urine after consumption of charbroiled or fried beef. Mutat. Res. 2002.163-173, 506-507. 

The potential of a natural anthocyanin with purple corn color (PCC) has been tested against colorectal carcinogenesis, using male F344/DuCrj rats that were initially treated with 1,2-dimethylhydrazine (DMH). 2-Amino-l-melhyl-6-phenylimidazo [4,5-fc] pyridine (PhIP) exerted promoting effects on... 

AMINO-3-METHYLPENTANOIC ACID see IKXOOO 2-AMINO-4-METHYLPENTANOIC ACID see LESOOO 2-AMINO-l-METHYL-6-PHENYLIMIDAZO(4,5-B)PYRIDINE see AKZ200... 

Diphenyl ketone reacts with )V-pyridin-2-yl-S,S-dimethylsulfilimine to give 3,3-di-phenylimidazo[l,2-a]pyridin-2(3i/)-one (79CPB2116), whereas reaction of the 2-methyl-pyridin-2-yl-S,S-dimethylsulfilimine with a variety of a-halocarbonyl compounds gave 3-substituted 5-methyl-2-methylthioimidazo[l,2-a]pyridines (78YZ631). 

In a slight variation of the above synthetic approach, 2-phenylimidazo[l,2-a]pyridine (290) was prepared by the reaction of l-phenacyl-2-chloropyridinium bromide (288) with ammonia (289) (55CBIII7). The use of primary amines (291) resulted in l-alkylimidazo[l,2-a]pyridinium halides (292) (69JOC2129), whereas hydroxylamine (293) gave imidazo[l,2-a]pyridine 1-oxides (294) (78JOC658). 

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