1775-95-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-nitrobenzophenone is used as an intermediate in the synthesis of various pharmaceutical compounds. One of its notable applications is in the synthesis of [5-(4-nitrophenyl)-2-furyl]acrylic acid substituted benzophenone, which is an anti-malarial agent. This application highlights its importance in the development of life-saving medications.
Used in Metabolite Research:
ANBP is also recognized as a metabolite of Nitrazepam, a benzodiazepine drug. Understanding the metabolic pathways and intermediates, such as ANBP, can be crucial for studying the drug's effects, safety, and potential side effects in the medical field.

Synthesis Reference(s)

Synthetic Communications, 16, p. 485, 1986 DOI: 10.1080/00397918608057727

InChI:InChI=1/C13H10N2O3/c14-12-7-6-10(15(17)18)8-11(12)13(16)9-4-2-1-3-5-9/h1-8H,14H2

Upstream product

• 41019-22-1 N-(2-Benzoyl-4-nitro-phenyl)-acetamide 
• 34052-37-4 2-chloro-5-nitrobenzophenone 
• 1775-94-6 N-(2-benzoyl-4-nitrophenyl)benzamide 
• 3393-96-2 p-nitrobenzanilide 
• 38735-62-5 5-nitro-3-phenyl-2,1-benzisoxazole 
• 146-22-5 nitrazepam 
• 2011-69-0 2-amino-N-(2-benzoyl-4-nitrophenyl)acetamide 
• 2243-80-3 3-nitrobenzophenone 
• 72875-17-3 2-Amino-5-nitrobenzophenone N,N-dimethylhydrazone 
• 7664-41-7 ammonia 
• 25784-91-2 2-chloro-5-nitrobenzoylchloride 
• 71-43-2 benzene 
• 41018-87-5 2-methyl-3-phenyl-5-nitroindole 
• 70063-29-5 benzyl methyl ketone p-nitrophenylhydrazone 

Downstream Products

• 50885-17-1 2-(2,2,2-trifluoroethylamino)-5-nitrobenzophenone 
• 41019-22-1 N-(2-Benzoyl-4-nitro-phenyl)-acetamide 
• 26412-32-8 2-(2-Amino-5-nitro-α-phenylbenzylidenamino)ethanol 
• 58045-64-0 6-nitro-4-phenylquinazoline 
• 10456-80-1 2-N-carbethoxymethyl-5-nitrobenzophenone 
• 24042-91-9 2-(p-Toluolsulfonamido)-5-nitrobenzophenon 
• 122438-78-2 C₂₀H₁₇N₅O₂S 
• 121779-69-9 N-(2-benzoyl-4-nitrophenyl)-4-methoxybenzenesulfonamide 
• 38249-89-7 [(2-Benzoyl-4-nitro-phenylcarbamoyl)-methyl]-carbamic acid benzyl ester 
• 136623-25-1 C₁₄H₁₄N₆O₂*2ClH 
• 82221-46-3 6-Amino-hexanoic acid (2-benzoyl-4-nitro-phenyl)-amide 
• 18330-94-4 2,5-diaminobenzophenone 
• 5688-65-3 2,8-dinitro-6,12-diphenyl-dibenzo[b,f][1,5]diazocine 
• 265648-21-3 N-(2-benzoyl-4-nitrophenyl)-2-phenylacetamide 

Relevant academic research and scientific papers

2-amino-5-nitrobenzophenone and 2′-fluoro-2-methylamino-5-nitrobenzophenone

The title compounds, C13H10N2O3 and C14H11FN2O3, were prepared by acid degradation of the 1,4-benzodiazepine drugs nitrazepam and flunitrazepam, respectively. The structure of 2-amino-5-nitrobenzophenone reported here is a polymorphic form of a known structure.

Quinolinone compounds serving as selective phosphodiesterase 2 inhibitors and preparation method of quinolinone compounds

The invention belongs to the field of chemical medicines, and particularly relates to quinolinone compounds serving as selective phosphodiesterase 2 inhibitors and a preparation method of the quinolinone compounds. The invention provides the quinolinone compounds, the general formula of the quinolinone compounds is represented by a formula (A), and the quinolinone compounds have a high-intensity inhibition effect on PDE2 and have high selectivity on other PDE subtypes. The invention also provides a preparation method of the derivatives, and the preparation method is scientific, reasonable, simple and feasible. The quinolinone compounds disclosed by the invention are used for preparing medicines for treating memory and cognitive impairment, neurodegenerative diseases and cardiovascular diseases.

Elucidation of degradation behavior of nitrazepam and other benzodiazepines in artificial gastric juice: Study on degradability of drugs in stomach (II)

The degradation behavior of eight benzodiazepines (BZPs): alprazolam, etizolam, diazepam, triazolam, nitrazepam (NZP), flunitrazepam (FNZ), bromazepam, and lorazepam, in artificial gastric juice was monitored by a LC/photodiode array detector (PDA) to estimate their pharmacokinetics in the stomach. For drugs that were degradable, such physicochemical parameters as reaction rate constant were measured to evaluate the effect of storage conditions on drug degradability, such as whether the degradation proceeds faster by increasing storage temperature, or whether the degradation reaction is reversible by adjusting pH. As a result, it was confirmed that although the eight BZPs degraded in artificial gastric juice, most of them could be restored when pH was increased, and the restoration rates differed depending on the pH and the type of BZP. As for NZP, an Arrhenius plot was drawn to obtain the physicochemical parameters, such as activation energy and activation entropy involved in the degradation reaction, and the reaction kinetics was discussed. In addition, two substances were confirmed as the degradation products of NZP in artificial gastric juice: one was a reversible degradation product (A) (intermediate) and the other was an irreversible degradation product (B) (final degradation product). The intermediate was identified as 2-amino-N-(2-benzoyl-4-nitrophenyl)-acetamide, and the final degradation product was 2-amino-5-nitrobenzophenone. Therefore, when detecting NZP in human stomach contents, such as during judicial dissection, it would be prudent to target NZP as well as the intermediate (A) and the final degradation product (B).

Polymer-incarcerated palladium-catalyzed facile: In situ carbonylation for the synthesis of aryl aldehydes and diaryl ketones using CO surrogates under ambient conditions

In this existing work, an efficient polymer-supported palladium catalyst, a furfurylamine-functionalized Merrifield complex of palladium [Pd@(Merf-FA)], was synthesized and characterized, showing excellent catalytic activity towards in situ carbonylation reactions using carbon monoxide surrogates like formic acid and chloroform. Herein, we examined the catalytic activity of the Pd@(Merf-FA) catalyst for the formylation of aryl iodides and carbonylative Suzuki-Miyaura coupling reactions. The Pd@(Merf-FA) catalyst was systematically characterized by several techniques like HRTEM, elemental mapping, PXRD, TGA-DTA, FESEM, UV-vis, EDAX, CHN and AAS analysis. The catalyst is highly recyclable, able to be recycled up to six times without showing any significant decrease in catalytic activity. The [Pd@(Merf-FA)] catalyst proved to be more efficient compared to the corresponding homogeneous palladium catalyst. In addition, the leaching experiment of the synthesized catalyst was studied, which showed that negligible leaching of metal occurred from the polymeric support.

Concise Synthesis of 4-Arylquinolines via Intramolecular Cyclization of Allylamines and Ketones

The intramolecular cyclization of allylamines and ketones was achieved in the presence of potassium tert-butoxide and N,N-dimethylformamide. A series of 4-arylquinolines was prepared in good yields. The reaction could be accomplished at room temperature using only a substoichiometric amount of potassium tert-butoxide. On the other hand, the reaction of the structurally analogous allyl ethers afforded diverse products. The reaction may proceed via the rearrangement of α-aminoallyl radicals and the generation of nucleophilic enamine intermediates. This finding represents a new strategy for the synthesis of quinoline derivatives from readily available 2-(allylamino)phenyl ketones.

Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: Synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles

A palladium-catalyzed direct addition of arylboronic acids to unprotected 2-aminobenzonitriles has been developed, leading to a wide range of 2-aminobenzophenones with moderate to excellent yields. The transformation has broad scope and high functional group tolerance. Moreover, 2-oxoindoline-7-carbonitrile and indole-7-carbonitrile were applicable to this process for the construction of 7-benzoyl-2-oxoindolines and 7-benzoylindoles, respectively. Among the compounds examined, compound 4e possessed the most potent anticancer activity against H446 and HGC-27 in vitro, with IC50 values of 0.02 μmol L-1 and 0.09 μmol L-1, respectively, while compound 4a showed the best potent anticancer activity against SGC-7901 with an IC50 value of 0.01 μmol L-1. Furthermore, we also performed in silico molecular docking calculations to investigate the interaction mode and binding affinity between the examined compounds and their tubulin target. This journal is

Palladium-catalyzed direct addition of 2-Aminobenzonitriles to sodium arylsulfinates: Synthesis of o-Aminobenzophenones

The first example of the palladium-catalyzed synthesis of o-Aminobenzophenones in moderate to excellent yields via a direct addition of sodium arylsulfinates to unprotected 2-Aminobenzonitriles was reported. A plausible mechanism for the formation of o-Aminobenzophenones involving desulfination and addition reactions was proposed. The utility of this transformation was demonstrated by its compatibility with a wide range of functional groups. Thus, the method represents a convenient and practical strategy for synthesis of o-Aminobenzophenones.

Design, synthesis and evaluation of aminobenzophenone derivatives containing nitrogen mustard moiety as potential central nervous system antitumor agent

A series of novel substituted aminobenzophenone derivatives containing nitrogen mustard moiety (5a-f) were synthesized and characterized on the basis of their IR, 1H NMR, 13C NMR, CHN, and mass spectral data. All the compounds when evaluated for chemical 4-(4-nitrobenzyl) pyridine alkylating activity proved to be active alkylating agents. All the synthesized compounds were subjected to physicochemical parameters determination required for central nervous system (CNS) activity through computational, online software, and QikProp 3.2. The log P values and other in silico ADME physicochemical descriptors analyzed lay between the ranges those are required for good BBB penetration. The in vitro antiproliferative activity against human cancer cell lines viz. A 549 (lung), COLO 205 (colon), U 87 (glioblastoma), and IMR-32 (neuroblastoma) was investigated. Most of the test compounds showed potent antitumor activity, especially compound (5f) which displayed the highest activity against CNS cancer cell line comparable to that of chlorambucil and docetaxel. The preliminary structure-activity relationship (SAR) revealed that 5-chloroaminobenzophenone-mustard series (5a-c) exhibited better antitumor activity than 5-nitroaminobenzophenone-mustard series (5d-f).

Catalytic reduction of ortho - And para -azidonitrobenzenes via tert -butoxide ion mediated electron transfer

The reduction of a range of substituted azidonitrobenzene derivatives to the corresponding aniline is described. The chemoselective reaction proceeds cleanly and in good yield, generating minimal waste products. The process involves a thiazolium salt derived species which is proposed as a radical anion relay, with tert-butoxide as the stoichiometric reductant.

D-Glucosamine as a green ligand for copper catalyzed synthesis of primary aryl amines from aryl halides and ammonia

Replacing conventional reagents with environment friendly reagents is one of the primary goals of modern synthetic methodology and in this very primitive study about utilizing green, naturally available carbohydrate molecules as ligands in transition metal catalyzed reactions, we report Cu/d-glucosamine as an efficient catalyst for aniline synthesis.