4463-22-3

Usage

Uses

Used in Pharmaceutical Industry:
N-hydroxy-4-acetylaminobiphenyl is used as an active pharmaceutical ingredient for its potential therapeutic effects. The expression is: N-hydroxy-4-acetylaminobiphenyl is used as an active pharmaceutical ingredient for its potential therapeutic effects.
Used in Chemical Research:
In the field of chemical research, N-hydroxy-4-acetylaminobiphenyl serves as a valuable compound for studying the properties and reactions of hydroxamic acid derivatives. The expression is: N-hydroxy-4-acetylaminobiphenyl is used as a research compound for studying the properties and reactions of hydroxamic acid derivatives.
Used in Material Science:
N-hydroxy-4-acetylaminobiphenyl can be utilized in the development of new materials, such as polymers or coatings, due to its unique chemical structure and properties. The expression is: N-hydroxy-4-acetylaminobiphenyl is used as a building block for the development of new materials in material science.
Used in Analytical Chemistry:
N-hydroxy-4-acetylaminobiphenyl can also be employed as a reference material or standard in analytical chemistry for the calibration of instruments and the development of new analytical methods. The expression is: N-hydroxy-4-acetylaminobiphenyl is used as a reference material or standard in analytical chemistry for calibration and method development.

InChI:InChI=1/C14H13NO2/c1-11(16)15(17)14-9-7-13(8-10-14)12-5-3-2-4-6-12/h2-10,17H,1H3

Upstream product

• 811-98-3 d⁽⁴⁾-methanol 
• 26541-56-0 N-acetoxy-N-acetylaminobiphenyl (AAABP) 
• 10125-76-5 4-nitroso-1,1′-biphenyl 
• 127-17-3 2-oxo-propionic acid 
• 92-93-3 1-phenyl-4-nitrobenzene 
• 431-03-8 dimethylglyoxal 
• 6810-26-0 4-hydroxylaminobiphenyl 
• 75-36-5 acetyl chloride 

Downstream Products

• 26541-56-0 N-acetoxy-N-acetylaminobiphenyl (AAABP) 
• 1426845-68-2 8-[acetyl(4-biphenylyl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine 

Relevant academic research and scientific papers

Catalyst-free generation of acyl radicals induced by visible light in water to construct C-N bonds

We describe herein a catalyst-free and redox-neutral photochemical strategy for the direct generation of acyl radicals from α-diketones, and its selective conversion of nitrosoarenes to hydroxyamides or amides with AcOH or NaCl as an additive. The reaction was carried out under mild conditions in water with purple LEDs as the light source. A broad scope of substrates was demonstrated. Mechanistic experiments indicate that α-diketones cleave to give acyl radicals, with hydroxyamides being further reduced to amides.

Synthesis method of N-acylhydroxylamine

The invention relates to a synthesis method of N-acylhydroxylamine, which comprises the following steps: starting from o-diketone and a nitroso compound, and adding an acid thereby efficiently obtaining the structure of N-acylhydroxylamine under the irradiation of visible light or ultraviolet light, wherein a part of the obtained product is an important biomedical chemical intermediate. Accordingto the method, the o-diketone and the nitroso compound which are cheap and easy to obtain are used as raw materials, only visible light or ultraviolet light irradiation is needed, cheap acid is addedin the reaction process, a catalyst or a metal compound is not needed, and only water can be used as a solvent in mass production. The whole production process is environmentally friendly, economical,efficient and low in cost, and has very remarkable advantages compared with the conventional production process.

Synthesis of site-specific damaged DNA strands by 8-(acetylarylamino)- 2′-deoxyguanosine adducts and effects on various DNA polymerases

Beside the predominately found 8-(arylamino)-2′-dG, 8-(acetylarylamino) damages within DNA-strands may also play an important role in the induction of chemical carcinogenesis. A synthesis pathway leading to these 8-(acetylarylamino)-dG adducts using different aromatic amines has been optimized. The 8-modified dGs were converted into the corresponding phosphoramidites and site-specifically incorporated into different oligonucleotides leading to DNA strands. Lesion-bearing hybrids of these damaged DNA-strands with complementary oligonucleotides were used to study their melting properties and their circular dichroism spectra. It was shown that no EcoRI restriction took place with the damage inside the cleavage site. Finally, three different DNA polymerases were used for primer extension studies. C8-NAc-Arylamine adducts of 2′-deoxyguanosine with various aromatic amines were synthesized by using cross-coupling reactions and converted into 3′-phosphoramidites. Site-specific damaged NarI-, EcoRI- and 20mer-oligonucleotides were prepared by automated DNA-synthesis. Biophysical properties, restriction endonuclease studies and DNA-polymerase assays were performed. Copyright

Nucleophilic Aromatic Substitution on Ester Derivatives of Carcinogenic N-Arylhydroxamic Acids by Aniline and N,N-Dimethylaniline

Decomposition of N-(pivaloyloxy)-2-(acetylamino)fluorene (1b) and N-(sulfonatooxy)-4-(acetylamino)biphenyl (2a) in MeOH occurs predominately via N-O bond cleavage to yield oxazoles (5, 6, 23), methoxy adducts (7, 8, 24, 25, 26), and rearrangement products

N-Arylhydroxamic Acids: Reaction of Nitroso Aromatics with α-Oxo Acids

A practical and high-yielding route to N-arylhydroxamic acids from nitroso aromatics and α-oxo acids 1a-d is desctibed.In aqueous and acetic acid containing media, the reactions exhibit second-order reaction kinetics overall.In the aqueous medium, the rate constant (kobsd) for N-phenylacetohydroxamic acid (8b) formation increased with increasing +>, though there were some side pathways involving azoxybenzene formation.In general, kobsd for the reaction in the acetic acid containing medium was about one-tenth of that in HCl at pH 0.6.On a preparative scale, acetic acid is better than HCl, in that both reactants showed sufficient solubilities in acetic acid for a high reaction velocity and no side reaction was detected.With this method, the proximate carcinogens, N-(4-biphenylyl)acetohydroxamic acid (12b) and N-(2-fluorenyl)acetohydroxamic acid (13b), could be easily prepared.Under both conditions, the order of kobsd for the reactions of nitrosobenzene (2) with α-oxo acids 1a-d was glyoxylic (1a) > pyruvic (1b) 2-oxobutyric (1c) > benzoylformic (1d) acid.For the reactions of substituted nitrosobenzenes 3-6 with pyruvic acid (1b), the order of kobsd was p-phenyl (6) > unsubstituted (2) > p-chloro (5) > m-chloro (4) >> o-chloro (3) nitrosobenzene.The negative Hammett reaction constant value obtained indicates that an electron-donating substituent is preferable for the reaction.The reaction mechanism and other factors affecting N-arylhydroxamic acid formation are also descussed.

The Solvolysis of N-Acetoxy-2-acetylaminofluorene and N-Acetoxy-4-acetylaminobiphenyl: Delicate Balance between Nitrenium Ion Formation and Hydrolysis

The solvolysis of N-acetoxy-2-acetylaminofluorene in aqueous acetone at neutral pH proceeds exclusively with nitrenium ion formation while under the same conditions, the 4-aminobiphenyl analogue undergoes exclusive acyl-oxygen scission.

Arylhydroxamic acid N,O-acyltransferase substrates. Acetyl transfer and electrophile generating activity of N-hydroxy-N-(4-alkenyl-, and 4-cyclohexylphenyl)acetamides

Arylhydroxamic acid N,O-acyltransferase (AHAT) is an enzyme system that is capable of converting many N-arylhydroxamic acids into reactive electrophilic species. As part of an investigation into the influence of the structure of the aryl group upon the ability of N-arylhydroxamic acids to serve as substrates for AHAT, a series of N-hydroxy-N-(4-alkyl-, 4-alkenyl-, and 4-cyclohexylphenyl) acetamides was prepared and evaluated in vitro with partially purified rat and hamster hepatic AHAT. The nature of the 4-substituent markedly influenced the ability of the hydroxamic acids to serve as acetyl donors in the AHAT-catalyzed transacetylation of 4-aminoazobenzene (AAB). As the length of the 4-substituent was increased from methyl to pentyl, the compounds became increasingly more effective substrates. The compounds containing vinyl, propenyl, and 2-methylpropenyl 4-substituents were more effective acetyl donors than the corresponding compounds containing saturated 4-substituents. The three most effective AHAT substrates in the AAB transacetylation assay were N-hydroxy-N-(4-pentylphenyl)- (7), N-hydroxy-N-(4-propenylphenyl)- (10), and N-hydroxy-N-[4-(2-methylpropenyl)phenyl]acetamide (11), each of which was approximately as active as the standard compound, N-hydroxy-4-acetamidobiphenyl (1), with rat hepatic AHAT and approximately 60% as active as 1 with hamster hepatic AHAT. Both 1 and N-hydroxyl-N-(4-cyclohexylphenyl)acetamide (8) were activated by hamster hepatic AHAT to yield electrophilic intermediates that formed adducts with 2-mercaptoethanol. The 2-mercaptoethanol adducts were characterized by mass spectrometry and were identified as 4-phenyl-2-[(2-hydroxyethyl)thio]aniline (22) and 4-cyclohexyl-2-[(2-hydroxyethyl)thio]aniline (21). The structure of compounds 21 and 22 were confirmed by an unambiguous chemical synthesis. Both compounds 1 and 8 irreversibly inactivated hamster hepatic AHAT by a time-dependent process. The results of the inactivation experiments confirmed that 1 inactivates AHAT primarily via a suicide substrate mechanism and revealed that 8 inactivates the enzyme by a process consisting primarily of a pathway in which electrophiles are released into the medium and subsequently react with nucleophiles present on AHAT.