42771-77-7

Usage

Uses

Used in Chemical Synthesis:
1-(2-NITRO-BIPHENYL-4-YL)-ETHANONE is used as a reagent for the reductive cyclization of nitrobiphenyls and nitrostyrenes to carbazoles and indoles. This application is essential in the synthesis of various organic compounds, particularly those with potential pharmaceutical and industrial applications.
In the Pharmaceutical Industry:
1-(2-NITRO-BIPHENYL-4-YL)-ETHANONE is used as a key intermediate in the synthesis of certain pharmaceutical compounds. Its ability to participate in reductive cyclization reactions allows for the creation of complex molecular structures that can be further developed into potential drug candidates.
In the Chemical Industry:
1-(2-NITRO-BIPHENYL-4-YL)-ETHANONE is utilized as a building block in the production of various chemicals, including dyes, pigments, and other specialty chemicals. Its versatility in chemical reactions makes it a valuable component in the development of new materials with specific properties and applications.

Upstream product

• 5465-65-6 4-chloro-3-nitroacetophenone 
• 98-80-6 phenylboronic acid 
• 42771-79-9 3'-fluoro-4'-phenylacetophenone 
• 18640-58-9 3-nitro-4-bromoacetophenone 
• 2719-21-3 4-(N-acetylamino)acetophenone 
• 1432-42-4 1-(4-amino-3-nitrophenyl)ethanone 
• 71-43-2 benzene 

Downstream Products

• 42771-78-8 1-[2-amino(1,1'-biphenyl)-4-yl]ethan-1-one 
• 23592-74-7 2-acetylcarbazole 

Relevant academic research and scientific papers

Synthesis, biological evaluation and structure-activity relationship of novel dichloroacetophenones targeting pyruvate dehydrogenase kinases with potent anticancer activity

Pyruvate dehydrogenase kinases (PDKs) are promising therapeutic targets that have received increasing attentions in cancer metabolism. In this paper, we report the synthesis and biological evaluation of a series of novel dichloroacetophenones as potent PDKs inhibitors. Structure-activity relationship analysis enabled us to identify a potent compound 6u, which inhibited PDKs with an EC50 value of 0.09 μM, and reduced various cancer cells proliferation with IC50 values ranging from 1.1 to 3.8 μM, while show weak effect against non-cancerous L02 cell (IC50 > 10 μM). In the A375 xenograft model, 6u displayed an obvious antitumor activity at a dose of 5 mg/kg, but with no negative effect to the mice weight. Molecular docking suggested that 6u formed direct hydrogen bond interactions with Ser75 and Gln61 in PDK1, and meanwhile the aniline skeleton in 6u was sandwiched by the conserved hydrophobic residues Phe78 and Phe65, which contribute to the biochemical activity improvement. Moreover, 6u induced A375 cell apoptosis and cell arrest in G1 phase, and inhibited cancer cell migration. In addition, 6u altered glucose metabolic pathway in A375 cell by decreasing lactate formation and increasing ROS production and OCR consumption, which could serve as a potential modulator to reprogram the glycolysis pathway in cancer cell.

A Highly Efficient Pd(PPh3)4-Catalyzed Suzuki Cross-Coupling Method for the Preparation of 2-Nitrobiphenyls from 1-Chloro-2-nitrobenzenes and Phenylboronic Acids

A simple and efficient method for Suzuki cross-coupling of highly substituted and congested 1-chloro-2-nitrobenzene with phenylboronic acid was developed, investigated, and optimized. The reaction conditions comprises a mixture of MeOH and water (4:1) as the reaction medium, readily available and cheap Pd(PPh3)4 as catalyst, sodium carbonate as base, and microwave heating, which affords a fast reaction rate with good outcomes. The procedure was proven to have high functional group tolerance with phenylboronic acid and for 1-chloro-2-nitrobenzene and thus is a general method for the synthesis of 2-nitrobiphenyl. The target scaffold, 2-nitrobiphenyls, was produced in excellent yields with excellent selectivities in all cases. An efficient microwave-assisted and Pd(PPh3)4-catalyzed Suzuki cross-coupling method for the synthesis of 2-nitrobiphenyls from 1-chloro-2-nitrobenzenes and phenylboronic acids is disclosed. The method exhibits excellent selectivity and fast reaction rates, provides high to excellent yields, and tolerates both electron-withdrawing and -donating groups.

Triphenylphosphine-mediated reductive cyclization of 2-nitrobiphenyls: A practical and convenient synthesis of carbazoles

The synthesis of a series of substituted carbazoles from the corresponding 2-nitrobiphenyl derivatives using a novel modification of the Cadogan reaction is described. Cyclization of the 2-nitrobiphenyls was achieved via reductive deoxygenation of the nitro groups using a slight excess of triphenylphosphine in a suitable solvent. We have observed a temperature dependence on the extent of conversion under these conditions, with higher boiling solvents affording higher yields across a range of substrates. The new reaction conditions are very straightforward and convenient to execute, tolerate a broad range of functional groups, and yield carbazole products in the absence of unwanted side products.

Prostaglandin synthase inhibitors

This invention relates to ortho substituted phenyl compounds as inhibitors of prostaglandin synthase, to pharmaceutical compositions comprising such compounds and to methods of using such compounds as antiinflammatory and antipyretic agents. The class of compounds useful in this method of treatment is represented by Formula I below: STR1

Therapeutically active phenylalkane derivatives

2-(2-Fluoro-4-biphenylyl)propan-1-ol, 2-(2'-Fluoro-4-biphenylyl)propan-1-ol and 2-(2,2'-Difluoro-4-biphenylyl)propan-1-ol Possessing great anti-inflammatory, analgesic and antipyretic activities.