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[ CAS No. 99-55-8 ] {[proInfo.proName]}

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Chemical Structure| 99-55-8
Chemical Structure| 99-55-8
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Product Citations

Product Citations

Boyao Zhang ; George-Eugen Maftei ; Bartosz Bartmanski , et al. DOI:

Abstract: Organic carcinogens, in particular DNA-reactive compounds, contribute to the irreversible initiation step of tumorigenesis through introduction of genomic instability. Although carcinogen bioactivation and detoxification by human enzymes has been extensively studied, carcinogen biotransformation by human-associated bacteria, the microbiota, has not yet been systematically investigated. We tested the biotransformation of 68 mutagenic carcinogens by 34 bacterial species representative for the upper and lower human gastrointestinal tract and found that the majority (41) of the tested carcinogens undergo bacterial biotransformation. To assess the functional consequences of microbial carcinogen metabolism, we developed a pipeline to couple gut bacterial carcinogen biotransformation assays with Ames mutagenicity testing and liver biotransformation experiments. This revealed a bidirectional crosstalk between gut microbiota and host carcinogen metabolism, which we validated in gnotobiotic mouse models. Overall, the systematic assessment of gut microbiota carcinogen biotransformation and its interplay with host metabolism highlights the gut microbiome as an important modulator of exposome-induced tumorigenesis.

Purchased from AmBeed: ; ; ; ; ; 117-39-5 ; ; ; ; 62-44-2 ; ; ; ; ; ; ; ; ; ; ; 101-61-1 ; ; ; ; ; ; 90-94-8 ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ;

Product Details of [ 99-55-8 ]

CAS No. :99-55-8 MDL No. :MFCD00007741
Formula : C7H8N2O2 Boiling Point : -
Linear Structure Formula :C6H3(CH3)(NO2)(NH2) InChI Key :DSBIJCMXAIKKKI-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :7444
Synonyms :

Safety of [ 99-55-8 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P273-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405-P501 UN#:2660
Hazard Statements:H301+H311+H331-H412 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 99-55-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 99-55-8 ]

[ 99-55-8 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 99-55-8 ]
  • [ 404844-11-7 ]
  • 2
  • [ 99-55-8 ]
  • [ 483324-01-2 ]
  • [ 152460-09-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In butan-1-ol; for 38h;Heating / reflux; A 250 ml reactor, equipped with a mechanical stirrer and a reflux condenser, was charged with 2-chloro-4-(3-pyridyl)-pyrimidine (0.5 g, 2.6 mmol), 2-amino-4-nitrotoluene (0.5 g, 3.2 mmol), n-butanol (15 ml) and concentrated HCl (5 drops) and the mixture was refluxed for 38 hours. Then, the mixture was cooled, and 6 N NaOH was added to pH 8. The solvent was evaporated under reduced pressure and water (20 ml) was added to the residue, followed by extraction with dichloromethane (2×20 ml). The combined organic phase was concentrated to dryness to give the crude N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-pyrimidine-amine, which was purified by column chromatography to yield a product having 80% purity. The residue was re-slurried twice in methanol (2×2 ml) and in water (3 ml) and dried under reduced pressure
290 g With copper(l) iodide; 2-(dimethylamino)ethyl methacrylate; potassium carbonate; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere; 190 g of 2-chloro-4-(pyridin-3-yl)pyridine under a nitrogen atmosphere,167 g of 2-methyl-5-nitroaniline, 47 g of cuprous iodide,Anhydrous potassium carbonate 276gAnd 22 g of dimethylaminoethyl methacrylate added to 1,4-dioxane solution 2000 mLMedium, heating at 100 C, reaction for 20 h, TLC detection,The raw material is completely reacted; first under reduced pressure,Evaporate most of the solvent dioxane, after cooling to room temperature,The reaction mixture was poured into ice water and a large amount of white solid precipitated.Filtration, a small amount of n-hexane rinse, vacuum dry to pureN-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidinamine 290 g.
  • 3
  • [ 1194-21-4 ]
  • [ 99-55-8 ]
  • [ 1467739-25-8 ]
YieldReaction ConditionsOperation in experiment
60% at 170℃; for 3h; 6-Amino-4-chloropyrimidin-2(1H)-one (3, 200 mg, 0.84 mmol) and 2-methyl-5-nitroaniline (627 mg, 2.52 mmol) were heated at 170 °C for 3 h. The mixture was then cooled to rt and diethyl ether was added. The mixture was sonicated for 5 min. The suspension was filtered, and the filter cake was dissolved in MeOH and purified by column chromatography (silica gel, dichloromethane/methanol 9:1 v/v) to afford 4 (128 mg, 60percent) as a brown solid.
  • 4
  • [ 99-55-8 ]
  • [ 50593-30-1 ]
  • 5
  • [ 13721-01-2 ]
  • [ 99-55-8 ]
  • C17H13N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 150℃; for 0.333333h;Microwave irradiation; To a solution of 4-hydroxy-quinoline-3-carboxylic acid (A-1) (50 mg, 0.26 mmol), HBTU (99 mg, 0.26 mmol) and DIEA (138 muL, 0.79 mmol) in THF (2.6 mL) was added 2-methyl-5-nitro-phenylamine (40 mg, 0.26 mmol). The mixture was heated at 150° C. in the microwave for 20 min and the resulting solution was concentrated. The residue was dissolved in EtOH (2 mL) and SnCl2.2H2O (293 mg, 1.3 mmol) was added. The reaction was stirred at room temperature overnight. The reaction mixture was basified with sat. NaHCO3 solution to pH 7-8 and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was dissolved in DMSO and purified by HPLC (10-99percent CH3CN/H2O) to yield the product, N-(5-amino-2-methyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (94) (6 mg, 8percent). HPLC ret. time 2.06 min, 10-99percent CH3CN, 5 min run; ESI-MS 294.2 m/z (MH+).
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