6810-26-0

Usage

Uses

Used in Organic Synthesis:
N-HYDROXY-4-AMINOBIPHENYL is used as a synthetic building block for the creation of various organic compounds. Its chemical structure allows it to be a versatile intermediate in the synthesis of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-HYDROXY-4-AMINOBIPHENYL is used as a key intermediate in the development of new drugs. Its unique chemical properties enable the creation of novel drug candidates with potential therapeutic applications.
Used in Chemical Research:
N-HYDROXY-4-AMINOBIPHENYL is also utilized in chemical research as a model compound to study various reaction mechanisms and to develop new synthetic methodologies. Its reactivity and structural features make it an attractive candidate for exploring new chemical transformations and understanding fundamental organic chemistry concepts.
Used in Material Science:
In the field of material science, N-HYDROXY-4-AMINOBIPHENYL can be used as a component in the development of new materials with specific properties, such as conductivity, magnetism, or optical characteristics. Its incorporation into polymers or other materials can lead to the creation of novel materials with enhanced performance.

Safety Profile

Questionable carcinogen withexperimental carcinogenic data. Human mutation datareported. When heated to decomposition it emits highlytoxic fumes of NOx.

Upstream product

• 92-93-3 1-phenyl-4-nitrobenzene 
• 92-52-4 biphenyl 
• 60-29-7 diethyl ether 

Downstream Products

• 10125-76-5 4-nitroso-1,1′-biphenyl 
• 92-67-1 4-phenylalanine 
• 7334-12-5 1,2-di([1,1'-biphenyl]-4-yl)diazene oxide 
• 5326-53-4 1,2-di([1,1'-biphenyl]-4-yl)diazene 
• 26541-56-0 N-acetoxy-N-acetylaminobiphenyl (AAABP) 
• 4463-22-3 N-Hydroxy-4-acetylaminonbiphenyl 
• 7293-45-0 4-aminoterphenyl 
• 10569-67-2 4'-amino-o-terphenyl 
• 63344-48-9 [1,1':3',1-terphenyl]-4'-amine 
• 7285-66-7 3-chlorobiphenyl-4-amine 
• 866999-39-5 α-phenyl-N-(4-biphenyl)nitrone 
• 84283-08-9 N-(2′-deoxyguanosin-8-yl)-4-aminobiphenyl 
• 26690-77-7 N-Hydroxy-4-biphenylbenzamide 

Relevant academic research and scientific papers

Glucuronide conjugates of 4-aminobiphenyl and its N-hydroxy metabolites pH stability and synthesis by human and dog liver

Glucuronide conjugates of arylamines are thought to be important in the carcinogenic process. This study investigated the pH stability and synthesis of glucuronide conjugates of 4-aminobiphenyl and its N-hydroxy metabolites by human and dog liver. Both dog and human liver slices incubated with 0.06 mM [3H]-4-aminobiphenyl produced the N-glucuronide of 4-aminobiphenyl as the major product. After 2 hr of incubation, the N-glucuronide of 4-aminobiphenyl represented 52 and 27% of the total radioactivity recovered by HPLC in dog and human, respectively. When 4-aminobiphenyl, N-hydroxy-4-aminobiphenyl, or N-hydroxy-N-acetyl-4-aminobiphenyl was added to human microsomes containing [14C]UDP-glucuronic acid, a new product peak was detected by HPLC. At 0.5 mM, the rate of glucuronidation was N-hydroxy-N-acetyl-4-aminobiphenyl > N-hydroxy-4-aminobiphenyl > 4-aminobiphenyl. The rate of formation of the N-glucuronide of 4-aminobiphenyl was similar to that observed with benzidine and N-acetylbenzidine. The glucuronides of 4-aminobiphenyl and N-hydroxy-4-aminobiphenyl were both acid labile with T1/2 values of 10.5 and 32 min, respectively, at pH 5.5. The glucuronide of N-hydroxy-N-acetyl-4-aminobiphenyl was not acid labile with T1/2 values at pH 5.5 and 7.4 of 55 and 68 min, respectively. The glucuronide of 4-aminobiphenyl was the most acid labile conjugate examined. Thus, the glucuronide of 4-aminobiphenyl is a major product of dog and human liver slice metabolism and likely to play an important role in the carcinogenic process. BIOCHEM PHARMACOL 51;12:1679-1685, 1996.

A differential mobility spectrometry/mass spectrometry platform for the rapid detection and quantitation of DNA adduct dG-ABP

RATIONALE There is continued interest in exploring new analytical technologies for the detection and quantitation of DNA adducts, biomarkers which provide direct evidence of exposure and genetic damage in cells. With the goal of reducing clean-up steps and improving sample throughput, a Differential Mobility Spectrometry/Mass Spectrometry (DMS/MS) platform has been introduced for adduct analysis. METHODS A DMS/MS platform has been utilized for the analysis of dG-ABP, the deoxyguanosine adduct of the bladder carcinogen 4-aminobiphenyl (4-ABP). After optimization of the DMS parameters, each sample was analyzed in just 30 s following a simple protein precipitation step of the digested DNA. RESULTS A detection limit of one modification in 10 6 nucleosides has been achieved using only 2 μg of DNA. A brief comparison (quantitative and qualitative) with liquid chromatography/mass spectrometry is also presented highlighting the advantages of using the DMS/MS method as a high-throughput platform. CONCLUSIONS The data presented demonstrate the successful application of a DMS/MS/MS platform for the rapid quantitation of DNA adducts using, as a model analyte, the deoxyguanosine adduct of the bladder carcinogen 4-aminobiphenyl. Copyright 2013 John Wiley & Sons, Ltd. Copyright

Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids

This work represents the first [4+2] annulation of hydroxamic acids with olefins for the synthesis of benzo[c][1,2]oxazines scaffold via anode-selective electrochemical oxidation. This protocol features mild conditions, is oxidant free, shows high regioselectivity and stereoselectivity, broad substrate scope of both alkenes and hydroxamic acids, and is compatible with terpenes, peptides, and steroids. Significantly, the dioxygenation of olefins employing hydroxamic acid is also successfully achieved by switching the anode material under the same reaction conditions. The study not only reveals a new reactivity of hydroxamic acids and its first application in electrosynthesis but also provides a successful example of anode material-tuned product selectivity.

Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides

A facile approach for synthesizing ortho-bromoanilides from readily available aryhydroxylamines and thionyl bromide is demonstrated in this work. Mild reaction conditions and broad scope of substrates ranging from heterocyclic structures to pharmaceutics-potential motifs are used in the reactions of this paper. Efficient bromination of ortho C–H bonds of the aryhydroxylamines has been achieved. Ortho-bromoanilide products were obtained in good to excellent yields, and model scaled-up reactions of this synthetic approach are shown in this work.

Capturing labile sulfenamide and sulfinamide serum albumin adducts of carcinogenic arylamines by chemical oxidation

Aromatic amines and heterocyclic aromatic amines (HAAs) are a class of structurally related carcinogens that are formed during the combustion of tobacco or during the high temperature cooking of meats. These procarcinogens undergo metabolic activation by

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

ISOXAZOLIDINE DERIVATIVES

The present invention relates to novel anti-inflammatory and antiallergic compounds of the glucocorticosteroid series, methods of preparing such compounds, pharmaceutical compositions comprisingthem, combinations and therapeutic uses thereof. More particularly, the invention relates to glucocorticosteroids that are derivatives of isoxazolidine.

ISOXAZOLIDINE DERIVATIVES

Anti-inflammatory and antiallergic compounds of the glucocorticosteroid series according to formula (I) defined herein are useful for treating diseases of the respiratory tract characterized by airway obstruction.

Quantification of N-(deoxyguanosin-8-yl)-4-aminobiphenyl adducts in human lymphoblastoid TK6 cells dosed with N-hydroxy-4-acetylaminobiphenyl and their relationship to mutation, toxicity, and gene expression profiling

Gene expression profiles that are anchored to phenotypic endpoints may lead to the identification of signatures that predict mutagenicity or carcinogenicity. The study presented here describes the analysis of DNA adducts in the human TK6 lymphoblastoid ce

Synthesis and characterization of nucleoside derivatives, N-(benzoyl)-N-(deoxyguanosin-8-yl)-4-aminobiphenyl and N-(2′-deoxyguanosin-8-yl)-4-aminobiphenyl via α-phenyl-N-(4-biphenyl)nitrone

Lead tetraacetate (LTA) oxidation of α-Phenyl-N-(4-biphenyl)nitrone (8) to give a new ultimate carcinogen, N-acetoxy-N-benzoyl-4-aminobiphenyl (9) which was reacted with deoxyguanosine (dG) at pH 6.9 to give nucleoside derivative, N-(benzoyl)-N-(deoxyguan