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Home > Imidazoles > 124489-20-9
124489-20-9 | 2H-Imidazo[4,5-b]pyridin-2-one, 1,3-dihydro-1-methyl-6-phenyl-, oxime
CAS No: 124489-20-9 Catalog No: AG000M2K MDL No:
Product Description
Catalog Number:
AG000M2K
Chemical Name:
2H-Imidazo[4,5-b]pyridin-2-one, 1,3-dihydro-1-methyl-6-phenyl-, oxime
CAS Number:
124489-20-9
Molecular Formula:
C13H12N4O
Molecular Weight:
240.2606
IUPAC Name:
N-(1-methyl-6-phenylimidazo[4,5-b]pyridin-2-yl)hydroxylamine
InChI:
InChI=1S/C13H12N4O/c1-17-11-7-10(9-5-3-2-4-6-9)8-14-12(11)15-13(17)16-18/h2-8,18H,1H3,(H,14,15,16)
InChI Key:
DCVWQAGUQFBCTF-UHFFFAOYSA-N
SMILES:
ON=c1[nH]c2c(n1C)cc(cn2)c1ccccc1
Properties
Complexity:
282
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
240.101g/mol
Formal Charge:
0
Heavy Atom Count:
18
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
240.266g/mol
Monoisotopic Mass:
240.101g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
63A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.4
Literature
| Title | Journal |
|---|---|
| Metabolic Activation of the Cooked Meat Carcinogen 2-Amino-1-Methyl-6-Phenylimidazo[4,5-b]Pyridine in Human Prostate. | Toxicological sciences : an official journal of the Society of Toxicology 20180601 |
| Rabbit N-acetyltransferase 2 genotyping method to investigate role of acetylation polymorphism on N- and O-acetylation of aromatic and heterocyclic amine carcinogens. | Archives of toxicology 20170901 |
| Mapping serum albumin adducts of the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by data-dependent tandem mass spectrometry. | Chemical research in toxicology 20121015 |
| Mass spectrometric characterization of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine N-oxidized metabolites bound at Cys34 of human serum albumin. | Chemical research in toxicology 20111121 |
| Development and validation of a liquid chromatography-tandem mass spectrometry assay for the analysis of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and its metabolite 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine (N-OH-PhIP) in plasma, urine, bile, intestinal contents, faeces and eight selected tissues from mice. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100901 |
| Codominant expression of N-acetylation and O-acetylation activities catalyzed by N-acetyltransferase 2 in human hepatocytes. | The Journal of pharmacology and experimental therapeutics 20100801 |
| A comprehensive approach to the profiling of the cooked meat carcinogens 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, and their metabolites in human urine. | Chemical research in toxicology 20100419 |
| Proteomics of rat prostate lobes treated with 2-N-hydroxylamino-1-methyl-6-phenylimidazo[4,5-b]pyridine, 5alpha-dihydrotestosterone, individually and in combination. | International journal of oncology 20090901 |
| Biomonitoring of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and its carcinogenic metabolites in urine. | Chemical research in toxicology 20090601 |
| 4-Aminobiphenyl downregulation of NAT2 acetylator genotype-dependent N- and O-acetylation of aromatic and heterocyclic amine carcinogens in primary mammary epithelial cell cultures from rapid and slow acetylator rats. | Toxicological sciences : an official journal of the Society of Toxicology 20090101 |
| Quantitative investigation of the role of breast cancer resistance protein (Bcrp/Abcg2) in limiting brain and testis penetration of xenobiotic compounds. | Drug metabolism and disposition: the biological fate of chemicals 20080601 |
| Glucuronidation of PhIP and N-OH-PhIP by UDP-glucuronosyltransferase 1A10. | Carcinogenesis 20071101 |
| The cooked meat derived genotoxic carcinogen 2-amino-3-methylimidazo[4,5-b]pyridine has potent hormone-like activity: mechanistic support for a role in breast cancer. | Cancer research 20071001 |
| Enhanced glutathione S-transferase expression in 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine-resistant IEC-18 cells. | Cell biology and toxicology 20070501 |
| Mouse lung CYP1A1 catalyzes the metabolic activation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). | Carcinogenesis 20070301 |
| A comprehensive investigation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) metabolism in the mouse using a multivariate data analysis approach. | Chemical research in toxicology 20070301 |
| Uranyl nitrilotriacetate, a stabilized salt of uranium, is genotoxic in nontransformed human colon cells and in the human colon adenoma cell line LT97. | Toxicological sciences : an official journal of the Society of Toxicology 20061001 |
| Effects of single nucleotide polymorphisms in human N-acetyltransferase 2 on metabolic activation (O-acetylation) of heterocyclic amine carcinogens. | International journal of cancer 20060901 |
| 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) induces genetic changes in murine intestinal tumours and cells with ApcMin mutation. | Mutation research 20060430 |
| Malignant transformation of human colon epithelial cells by benzo[c]phenanthrene dihydrodiolepoxides as well as 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine. | Toxicology and applied pharmacology 20060415 |
| The impact of glucuronidation on the bioactivation and DNA adduction of the cooked-food carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in vivo. | Carcinogenesis 20051101 |
| PhIP carcinogenicity in breast cancer: computational and experimental evidence for competitive interactions with human estrogen receptor. | Chemical research in toxicology 20051001 |
| Differential metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in mice humanized for CYP1A1 and CYP1A2. | Chemical research in toxicology 20050901 |
| UGT1A1 polymorphisms are important determinants of dietary carcinogen detoxification in the liver. | Hepatology (Baltimore, Md.) 20050801 |
| Acyl glucuronidation of fluoroquinolone antibiotics by the UDP-glucuronosyltransferase 1A subfamily in human liver microsomes. | Drug metabolism and disposition: the biological fate of chemicals 20050601 |
| [Induction of uridine 5'-diphosphate-glucuronosyltransferase gene expression by sulforaphane and its mechanism: experimental study in human colon cancel cells]. | Zhonghua yi xue za zhi 20050330 |
| Human UDP-glucuronosyltransferase 1A1 is the primary enzyme responsible for the N-glucuronidation of N-hydroxy-PhIP in vitro. | Chemical research in toxicology 20040801 |
| Metabolic activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Syrian hamsters congenic at the N-acetyltransferase 2 (NAT2) locus. | Toxicological sciences : an official journal of the Society of Toxicology 20030801 |
| The effects of coffee on enzymes involved in metabolism of the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in rats. | Chemico-biological interactions 20030615 |
| Prostate expression of N-acetyltransferase 1 (NAT1) and 2 (NAT2) in rapid and slow acetylator congenic Syrian hamster. | Pharmacogenetics 20030301 |
| Mutagenesis and DNA adduct formation in the mouse mammary gland exposed to 2-hydroxyamino-1-methyl-6-phenylimidazo-[4,5-b]pyridine in whole organ culture. | Mutagenesis 20030101 |
| Metabolism of heterocyclic aromatic amines by human hepatocytes and cytochrome P4501A2. | Mutation research 20020930 |
| Resveratrol modulates human mammary epithelial cell O-acetyltransferase, sulfotransferase, and kinase activation of the heterocyclic amine carcinogen N-hydroxy-PhIP. | Cancer letters 20020808 |
| Heterologous expression of human N-acetyltransferases 1 and 2 and sulfotransferase 1A1 in Salmonella typhimurium for mutagenicity testing of heterocyclic amines. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20020801 |
| 2-Amino-1-methyl-6-(5-hydroxy-)phenylimidazo[4,5-b]pyridine (5-OH-PhIP), a biomarker for the genotoxic dose of the heterocyclic amine, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20020801 |
| Functional genomics of C190T single nucleotide polymorphism in human N-acetyltransferase 2. | Biological chemistry 20020601 |
| Excretion of the N(2)-glucuronide conjugate of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine in urine and its relationship to CYP1A2 and NAT2 activity levels in humans. | Carcinogenesis 20020501 |
| Differential metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in rat and human hepatocytes. | Carcinogenesis 20020101 |
| Cell transformation in vitro by food-derived heterocyclic amines Trp-P-1, Trp-P-2 and N(2)-OH-PhIP. | Toxicology 20010914 |
| Functional characterization of nucleotide polymorphisms in the coding region of N-acetyltransferase 1. | Pharmacogenetics 20010801 |
| N-glucuronidation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and N_hydroxy-PhIP by specific human UDP-glucuronosyltransferases. | Carcinogenesis 20010701 |
| N-Acetyltransferases, sulfotransferases and heterocyclic amine activation in the breast. | Pharmacogenetics 20010701 |
| The contribution of UDP-glucuronosyltransferase 1A9 on CYP1A2-mediated genotoxicity by aromatic and heterocyclic amines. | Carcinogenesis 20010601 |
| Induction of UDP-glucuronosyltransferase UGT1A1 by the flavonoid chrysin in Caco-2 cells--potential role in carcinogen bioinactivation. | Pharmaceutical research 20010301 |
| Protection against 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine cytotoxicity and DNA adduct formation in human prostate by glutathione S-transferase P1. | Cancer research 20010101 |
| Effects of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine on intestinal polyp development in Apc delta 716 knockout mice. | Molecular carcinogenesis 19960101 |
| Mutation and repair induced by the carcinogen 2-(hydroxyamino)-1-methyl-6-phenylimidazo[4,5-b]pyridine (N-OH-PhIP) in the dihydrofolate reductase gene of Chinese hamster ovary cells and conformational modeling of the dG-C8-PhIP adduct in DNA. | Chemical research in toxicology 19940101 |
| Metabolic activation and cytogenetic effects of 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine (PhIP) in Chinese hamster ovary cells expressing murine cytochrome P450 IA2. | Mutagenesis 19910701 |
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