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Friedländer synthesis of the food carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. 1995

S Lindström
Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala.

2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine has been prepared in 26% yield from 3-amino-2-phenylpropenal and creatinine which were heated with N,O-bis(trimethylsilyl)acetamide at 120 degrees C for 2 h. Under certain other conditions, the main product was a pyrimidine derivative.

UI MeSH Term Description Entries
D007093 Imidazoles Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D002273 Carcinogens Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. Carcinogen,Oncogen,Oncogens,Tumor Initiator,Tumor Initiators,Tumor Promoter,Tumor Promoters,Initiator, Tumor,Initiators, Tumor,Promoter, Tumor,Promoters, Tumor
D005036 Ethylmorphine A narcotic analgesic and antitussive. It is metabolized in the liver by ETHYLMORPHINE-N-DEMETHYLASE and used as an indicator of liver function. Ethomorphine,Dionine,Ethylmorphine Hydrochloride, (5alpha,6alpha)-Isomer,Ethylmorphine Hydrochloride, Dihydrate, (5alpha,6alpha)-Isomer,Ethylmorphine Sulfate (2:1), (5alpha,6alpha)-Isomer,Ethylmorphine, (5alpha,6beta)-Isomer,Trachyl
D005502 Food Substances taken in by the body to provide nourishment. Foods
D005965 Glucuronates Derivatives of GLUCURONIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that include the 6-carboxy glucose structure. Glucosiduronates,Glucuronic Acids,Acids, Glucuronic
D006358 Hot Temperature Presence of warmth or heat or a temperature notably higher than an accustomed norm. Heat,Hot Temperatures,Temperature, Hot,Temperatures, Hot
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

Related Publications

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Cancer chemoprevention from the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.
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PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine).
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Identification of N-(Deoxyguanosin-8-yl)-2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine as the major adduct formed by the food-borne carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, with DNA.
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N-acetyltransferase-dependent activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine: formation of 2-amino-1-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.
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