1432-42-4

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-3-NITRO-ACETOPHENONE is used as a key intermediate for the synthesis of flurbiprofen, a nonsteroidal anti-inflammatory drug (NSAID). It plays a vital role in the development of medications aimed at reducing inflammation, pain, and fever.
4-AMINO-3-NITRO-ACETOPHENONE is also used as a reagent in the chemical synthesis of other pharmaceutical compounds, contributing to the development of new drugs and therapies for various medical conditions. Its versatile chemical structure allows for further functionalization and modification, making it a valuable building block in the pharmaceutical industry.

InChI:InChI=1/C8H8N2O3/c1-5(11)6-2-3-7(9)8(4-6)10(12)13/h2-4H,9H2,1H3

Upstream product

• 7418-44-2 1-(4-acetylamino-3-nitrophenyl)ethanone 
• 2719-21-3 4-(N-acetylamino)acetophenone 
• 104503-83-5 4-acetyl-2-nitroazidobenzene 
• 7664-41-7 ammonia 
• 6277-38-9 1-(4-methoxy-3-nitrophenyl)ethanone 
• 88-74-4 2-nitro-aniline 
• 75-36-5 acetyl chloride 
• 400-93-1 3-nitro-4-fluoroacetophenone 
• 99-92-3 p-aminobenzophenone 
• 18640-58-9 3-nitro-4-bromoacetophenone 

Downstream Products

• 860575-80-0 4-acetyl-2-nitro-benzonitrile 
• 83570-42-7 1-(quinoxalin-6-yl)ethan-1-one 
• 21304-39-2 1-(3,4-diaminophenyl)ethanone 
• 7418-44-2 1-(4-acetylamino-3-nitrophenyl)ethanone 
• 97760-85-5 4'-amino-3'-bromo-5'-nitro-acetophenone 
• 121-89-1 3-Nitroacetophenone 
• 74902-59-3 4-amino-3-nitrophenacyl bromide 
• 42771-77-7 1-(2-nitro-1,1'-biphenyl-4-yl)ethan-1-one 
• 130623-37-9 4-(5,6-Dihydro-imidazo[2,1-b]thiazol-3-yl)-2-nitro-phenylamine; hydrobromide 
• 130623-15-3 1-(4-Amino-3-nitro-phenyl)-2-(4,5-dihydro-1H-imidazol-2-ylsulfanyl)-ethanone; hydrobromide 
• 18242-39-2 3,5-dinitrobromobenzene 
• 860554-21-8 4-acetyl-2-amino-benzoic acid amide 
• 189063-57-8 methyl 4-acetyl-2-aminobenzoate 
• 860561-25-7 4-acetyl-2-cyano-benzoic acid methyl ester 

Relevant academic research and scientific papers

1-Aryl-3-(4-methoxybenzyl)ureas as potentially irreversible glycogen synthase kinase 3 inhibitors: Synthesis and biological evaluation

Glycogen synthase kinase 3 (GSK-3)has become known for its multifactorial involvement in the pathogenesis of Alzheimer's disease. In this study, a benzothiazole- and benzimidazole set of 1-aryl-3-(4-methoxybenzyl)ureas were synthesised as proposed Cys199-targeted covalent inhibitors of GSK-3β, through the incorporation of an electrophilic warhead onto their ring scaffolds. The nitrile-substituted benzimidazolylurea 2b (IC50 = 0.086 ± 0.023 μM)and halomethylketone-substituted benzimidazolylurea 9b (IC50 = 0.13 ± 0.060 μM)displayed high GSK-3β inhibitory activity, in comparison to reference inhibitor AR-A014418 (1, IC50 = 0.072 ± 0.043)in our assay. The results suggest further investigation of 2b and 9b as potential covalent inhibitors of GSK-3β, since a targeted interaction might provide improved kinase-selectivity.

Identification, structure modification, and characterization of potential small-molecule SGK3 inhibitors with novel scaffolds

The serum and glucocorticoid-regulated kinase (SGK) family has been implicated in the regulation of many cellular processes downstream of the PI3K pathway. It plays a crucial role in PI3K-mediated tumorigenesis, making it a potential therapeutic target for cancer. SGK family consists of three isoforms (SGK1, SGK2, and SGK3), which have high sequence homology in the kinase domain and similar substrate specificity with the AKT family. In order to identify novel compounds capable of inhibiting SGK3 activity, a high-throughput screening campaign against 50,400 small molecules was conducted using a fluorescence-based kinase assay that has a Z' factor above 0.5. It identified 15 hits (including nitrogen-containing aromatic, flavone, hydrazone, and naphthalene derivatives) with IC50 values in the low micromolar to sub-micromolar range. Four compounds with a similar scaffold (i.e., a hydrazone core) were selected for structural modification and 18 derivatives were synthesized. Molecular modeling was then used to investigate the structure-activity relationship (SAR) and potential protein–ligand interactions. As a result, a series of SGK inhibitors that are active against both SGK1 and SGK3 were developed and important functional groups that control their inhibitory activity identified.

A Ratiometric Acoustogenic Probe for in Vivo Imaging of Endogenous Nitric Oxide

Photoacoustic (PA) imaging is an emerging imaging modality that utilizes optical excitation and acoustic detection to enable high resolution at centimeter depths. The development of activatable PA probes can expand the utility of this technology to allow for detection of specific stimuli within live-animal models. Herein, we report the design, development, and evaluation of a series of Acoustogenic Probe(s) for Nitric Oxide (APNO) for the ratiometric, analyte-specific detection of nitric oxide (NO) in vivo. The best probe in the series, APNO-5, rapidly responds to NO to form an N-nitroso product with a concomitant 91 nm hypsochromic shift. This property enables ratiometric PA imaging upon selective irradiation of APNO-5 and the corresponding product, tAPNO-5. Moreover, APNO-5 displays the requisite photophysical characteristics for in vivo PA imaging (e.g., high absorptivity, low quantum yield) as well as high biocompatibility, stability, and selectivity for NO over a variety of biologically relevant analytes. APNO-5 was successfully applied to the detection of endogenous NO in a murine lipopolysaccharide-induced inflammation model. Our studies show a 1.9-fold increase in PA signal at 680 nm and a 1.3-fold ratiometric turn-on relative to a saline control.

4-(Benzoimidazol-2-yl)-thiazole Compounds and Related Aza Derivatives

The invention relates to compounds of Formula (I) wherein ring A, X, (R1)n, R2, R3, R4, R4′, R5, n, and p are as described in the description; to pharmaceutically acceptable salts thereof, and to the use of such compounds as medicaments, especially as modulators of the CXCR3 receptor.

Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates

The present work reports on the synthesis, biological assaying and docking studies of a series of 12 aryl thiosemicarbazones, which were planned to act over two main enzymes, cruzain and trypanothione reductase. These enzymes are used as targets of trypanocidal activity in Chagas disease control with a minimal mutagenic profile. Three p-nitroaromatic thiosemicarbazones showed high activity against Trypanosoma cruzi in in vitro assays (IC50 57 μM), and no mutagenic profile was observed in micronucleous tests. Although the in vitro inhibition test showed that 10-μM doses of eight compounds inhibited cruzain activity, no correlation was found between cruzain inhibition and trypanocidal activity.

4-(BENZOIMIDAZOL-2-YL)-THIAZOLE COMPOUNDS AND RELATED AZA DERIVATIVES

The invention relates to compounds of Formula (I) wherein ring A, X, (R1)n, R2, R3, R4, R4', R5, n, and p are as described in the description; to pharmaceutically acceptable salts thereof, and to the use of such compounds as medicaments, especially as modulators of the CXCR3 receptor.

5-Acetyl-2-arylbenzimidazoles as antiviral agents. Part 4

Within a project aimed at discovering new Flaviviridae inhibitors, new variously substituted 2-phenylbenzimidazoles were synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against viruses representatives of the three genera of the Flaviviridae family, i.e.: Pestivirus (BVDV), Flavivirus (YFV) and Hepacivirus (HCV). Title compounds were also tested against RNA viruses representative of other single-stranded, positive-sense (ssRNA+) negative-sense (RNA-), or double-stranded (dsRNA) genomes, as well as against representatives of two DNA virus families. Nine compounds showed activity against BVDV (EC50 = 0.8-8.0 μM), compound 31 being the most potent (EC50 = 0.80 μM) and selective (SI = CC50/EC50 = >100). When tested in an HCV replicon assay, compound 31 resulted again the most potent, displaying an EC50 value of 1.11 μM and an SI of 100. Besides inhibiting BVDV, two compounds (35 and 38) showed a moderate activity also against YFV (EC 50 = 13 μM). Interestingly, 35 was moderately active also against RSV (EC50 = 25 μM).

11-PHENYL-DIBENZODIAZEPINE DERIVATIVES AS RXR-ANTAGONISTS

The present invention relates to novel benzodiazepine compounds exhibiting RXR-antagonist efficacy, for delaying progression of, preventing or treating a condition or disease being associated with RXR-antagonism, in particular selected from diabetes, comp

Zinc Mediated Friedel-Crafts Acylation in Solvent-Free Conditions under Microwave Irradiation

Zn powder is found to catalyze the Friedel-Crafts acylation of aromatic compounds with acyl halides efficiently under microwave irradiation in solvent-free conditions. Activated substrates undergo acylation predominantly at the para-position. The Zn powder can be re-used up to six times after simple washing with diethyl ether and dilute HCl.

1,2,3-Triazolo [1,5-a][1,4]- and 1,2,3-triazolo[l,5-a]-[1,5]benzodiazepine derivatives: Synthesis and benzodiazepine receptor binding

This paper reports the synthesis of new 1,2,3-triazolo[1,4]benzodiazepine and 1,2,3-triazolo[1,5]benzodiazepine derivatives and their evaluation toward benzodiazepine receptors. Receptor affinity gradually and remarkably increases by moving the nitrogen atom of the central ring from position 3 through 4 to position 5, to give the most effective compound 6a (K(i) = 150 nM). N-methylation of the diazepine ring (7a) lowers receptorial binding. Introduction of a chlorine atom on the benzene ring doubles the K(i) value (6b) which remains unaltered by the N-methylation (7b).