6277-38-9

Usage

Uses

Used in Chemical Synthesis:
4-METHOXY-3-NITROACETOPHENONE is used as a key intermediate in the synthesis of dimethylamino compounds. It is involved in the W2 Raney nickel catalyzed reductive methylation process, which is a crucial step in the production of these compounds.

Preparation

Preparation by reaction of acetyl chloride with 2-nitroanisole in the presence of aluminium chloride, ? in nitrobenzene at 0° ; ? in carbon disulfide.

InChI:InChI=1/C9H9NO4/c1-6(11)7-3-4-9(14-2)8(5-7)10(12)13/h3-5H,1-2H3

Upstream product

• 6322-56-1 4'-hydroxy-3'-nitroacetophenone 
• 77-78-1 dimethyl sulfate 
• 7446-70-0 aluminium trichloride 
• 91-23-6 2-Nitroanisole 
• 75-36-5 acetyl chloride 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 99-93-4 4-Hydroxyacetophenone 
• 7697-37-2 nitric acid 
• 186581-53-3 diazomethane 
• 67-56-1 methanol 
• 400-93-1 3-nitro-4-fluoroacetophenone 
• 5465-65-6 4-chloro-3-nitroacetophenone 
• 124-41-4 sodium methylate 

Downstream Products

• 109068-71-5 2-(4-methoxy-3-nitro-phenyl)-6-nitro-quinoline-4-carboxylic acid 
• 79885-02-2 2-(4-Methoxy-3-nitrophenyl)-N-phenyl-2-oxoessigsaeurethioamid 
• 83808-93-9 2-(4-Methoxy-3-nitro-phenyl)-pyrido[2,3-b]quinoxaline 
• 1432-42-4 1-(4-amino-3-nitrophenyl)ethanone 
• 65447-49-6 2-bromo-1-(3-nitro-4-methoxyphenyl)ethan-1-one 
• 424834-63-9 C₁₂H₁₄N₂O₄ 
• 109840-53-1 morpholino-acetic acid-(5-acetyl-2-methoxy-anilide) 
• 3117-18-8 N-(5-ethyl-2-methoxy-phenyl)-2-morpholin-4-yl-acetamide 
• 113016-89-0 5‐acetyl‐2‐methoxybenzonitrile 
• 79324-77-9 1‐(3‐iodo‐4‐methoxyphenyl)ethan‐1‐one 
• 861552-83-2 1,3-bis-(5-acetyl-2-methoxy-phenyl)-triazene 
• 74896-31-4 acetic acid-(5-acetyl-2-methoxy-anilide) 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of paralleled Aza resveratrol-chalcone compounds as potential anti-inflammatory agents for the treatment of acute lung injury

Acute lung injury (ALI) is a major cause of acute respiratory failure in critically-ill patients. It has been reported that both resveratrol and chalcone derivatives could ameliorate lung injury induced by inflammation. A series of paralleled Aza resveratrol-chalcone compounds (5a-5m, 6a-6i) were designed, synthesized and screened for anti-inflammatory activity. A majority showed potent inhibition on the IL-6 and TNF-α expression-stimulated by LPS in macrophages, of which compound 6b is the most potent analog by inhibition of LPS-induced IL-6 release in a dose-dependent manner. Moreover, 6b exhibited protection against LPS-induced acute lung injury in vivo. These results offer further insight into the use of Aza resveratrol-chalcone compounds for the treatment of inflammatory diseases, and the use of compound 6b as a lead compound for the development of anti-ALI agents.

Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium

Regardless of the sustainable development path, today, there are highly demanded chemical productions still operating that bear environmental and technological risks inherited from the previous century. The fabrication of nitro compounds, and nitroarenes in particular, is traditionally associated with acidic wastes formed in nitration reactions exploiting mixed acids. However, nitroarenes are indispensable for industrial and military applications. We faced the challenge and developed a greener, safer, and yet effective method for the production of nitroaromatics. The proposed approach comprises the application of an eco-friendly nitrating agent, namely dinitrogen pentoxide (DNP), in the medium of liquefied 1,1,1,2-tetrafluoroethane (TFE) - one of the most non-hazardous Freons. Importantly, the used TFE is not emitted into the atmosphere but is effortlessly recondensed and returned into the process. DNP is obtainedviathe oxidation of dinitrogen tetroxide with ozone. The elaborated method is characterized by high yields of the targeted nitro arenes, mild reaction conditions, and minimal amount of easy-to-utilize wastes.

Dichloroacetophenones targeting at pyruvate dehydrogenase kinase 1 with improved selectivity and antiproliferative activity: Synthesis and structure-activity relationships

Dichloroacetophenone is a pyruvate dehydrogenase kinase 1 (PDK1) inhibitor with suboptimal kinase selectivity. Herein, we report the synthesis and biological evaluation of a series of novel dichloroacetophenones. Structure-activity relationship analyses (SARs) enabled us to identify three potent compounds, namely 54, 55, and 64, which inhibited PDK1 function, activated pyruvate dehydrogenase complex, and reduced the proliferation of NCI-H1975 cells. Mitochondrial bioenergetics assay suggested that 54, 55, and 64 enhanced the oxidative phosphorylation in cancer cells, which might contribute to the observed anti-proliferation effects. Collectively, these results suggested that 54, 55, and 64 could be promising compounds for the development of potent PDK1 inhibitors.

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.

Synthesis and characterization of AlCl3 impregnated molybdenum oxide as heterogeneous nano-catalyst for the Friedel-Crafts acylation reaction in ambient condition

Aluminum trichloride (AlCl3) impregnated molybdenum oxide heterogeneous nano-catalyst was prepared by using simple impregnation method. The prepared heterogeneous catalyst was characterized by powder X-ray diffraction, FT-IR spectroscopy, solid-state NMR spectroscopy, SEM imaging, and EDX mapping. The catalytic activity of this protocol was evaluated as heterogeneous catalyst for the Friedel-Crafts acylation reaction at room temperature. The impregnated MoO4(AlCl2)2 catalyst showed tremendous catalytic activity in Friedel-Crafts acylation reaction under solvent-free and mild reaction condition. As a result, 84.0% yield of acyl product with 100% consumption of reactants in 18 h reaction time at room temperature was achieved. The effects of different solvents system with MoO4(AlCl2)2 catalyst in acylation reaction was also investigated. By using optimized reaction condition various acylated derivatives were prepared. In addition, the catalyst was separated by simple filtration process after the reaction and reused several times. Therefore, heterogeneous MoO4(AlCl2)2 catalyst was found environmentally benign catalyst, very convenient, high yielding, and clean method for the Friedel-Crafts acylation reaction under solvent-free and ambient reaction condition.

Aromatic nitration with bismuth nitrate in ionic liquids and in molecular solvents: A comparative study of Bi(NO3)3·5H 2O/[bmim][PF6] and Bi(NO3)3· 5H2O/1,2-DCE systems

A suspension of bismuth nitrate pentahydrate (BN) in [bmim][PF6] or [bmim][BF4] imidazolium ionic liquid (IL) is an effective reagent for ring nitration of activated aromatics under mild conditions without the need for external promoters. Nitration can also be effected in 1,2-DCE, MeCN, or MeNO2 without additives. Nitration of activated arenes (anisole, toluene, ethylbenzene, cumene, p-xylene, mesitylene, durene, and 1,3-dimethoxybenzene) is considerably faster (time to completion) in BN/[bmim][PF6] relative to BN/1,2-DCE and there are also differences in isomer distributions (for anisole, toluene, and ethylbenzene). With introduction of strongly deactivating substituents (-CHO; -MeCO; -NO 2) the BN/IL system is no longer active but reactions still proceed with BN/1,2-DCE in reasonable yields. The ready availability and low cost of BN, simple operation, and absence of promoters, coupled to recycling and reuse of the IL, provide an attractive alternative to classical nitration methods for activated arenes. Switching from Bi(NO3)3·5H 2O/[bmim][PF6] to Bi(NO3)3· 5H2O/1,2-DCE increases the scope of the substrates that can be nitrated.

Ethylammonium nitrate (EAN)/Tf2O and EAN/TFAA: Ionic liquid based systems for aromatic nitration

Acting as in situ sources of triflyl nitrate (TfONO2) and trifluoroacetyl nitrate (CF3COONO2), the EAN/Tf 2O and EAN/TFAA systems, generated via metathesis in the readily available ethylammonium nitrate (EAN) ionic liquid as solvent, are powerful electrophilic nitrating reagents for a wide variety of aromatic and heteroaromatic compounds. Comparative nitration experiments indicate that EAN/Tf2O is superior to EAN/TFAA for nitration of strongly deactivated systems. Both systems exhibit low substrate selectivity (K T/KB = 5-10) in (Figure presented) between values reported for covalent nitrates and preformed nitronium salts.

PYRIDAZINONE DERIVATIVE AND PDE INHIBITOR CONTAINING THE SAME AS ACTIVE INGREDIENT

It is to provide a novel pyridazinone derivative represented by the following general formula (1), which is useful as a pharmaceutical and has a phosphodiesterase inhibitory action: wherein R1 represents H or C1-6 alkyl, each of R2 and R3 represents H, X, C1-6 alkoxy, Z represents O or S, and A represents AA or BB, wherein AA represents: and BB represents: wherein R4 represents H or C1-6 alkyl, and each of R5 and R6 represents C1-6 alkyl.

Reaction of chalcones with basic hydrogen peroxide: A structure and reactivity study

Chalcone epoxides are important intermediates for the synthesis of 3,5-diarylpyrazoles. Twenty different chalcones were oxidized with hydrogen peroxide and potassium carbonate in order to produce the corresponding epoxides. The electronic nature of the substituents on the A- and B-ring of the chalcones significantly affected the reaction outcome: (i) electron donating groups on the A-and B-ring aided the reversion of the chalcones to the corresponding benzaldehydes, (ii) electron withdrawing groups on the B-ring promoted formation of the desired chalcone-epoxides in high chemical yields, and (iii) the presence of electron withdrawing groups (A-ring of the chalcones), regardless of the substituents on the B-ring, produced a mixture of epoxide, unreacted chalcone, benzaldehyde and acetophenone.

Scandium(III) trifluoromethanesulfonate catalyzed aromatic nitration with inorganic nitrates and acetic anhydride

The rare earth metal(III) trifluoromethanesulfonate (rare earth metal(III) triflate, RE(OTf)3) was found to be an efficient catalyst for aromatic nitration with carboxylic anhydride-inorganic nitrate as the nitrating agent. In the presence of a catalytic amount of RE(OTf)3, the nitration of substituted benzenes proceeded to afford the corresponding nitrobenzenes. Especially, scandium(III) trifluoromethanesulfonate (scandium(III) triflate, Sc(OTf)3) is the most active catalyst among our tested Lewis acids. It was also found that acetic anhydride-Al(NO 3) · 9H2O is the most active nitrating agent in this system.