42771-77-7

Basic information

• Product Name: 1-(2-NITRO-BIPHENYL-4-YL)-ETHANONE
• Synonyms: 1-(2-NITRO-BIPHENYL-4-YL)-ETHANONE;4-ACETYL-2-NITRO BIPHENYL;1-(2-Nitro-(1,1'-biphenyl)-4-yl)ethanone;3-Nitro-4-phenylacetophenone
• CAS NO: 42771-77-7
• Molecular Formula: C₁₄H₁₁NO₃
• Molecular Weight: 241.24204
• EINECS: 255-933-8
• Mol File: 42771-77-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 350.6°Cat760mmHg
• Flash Point: 156.6°C
• Appearance: /
• Density: 1.217g/cm³
• CAS DataBase Reference: 1-(2-NITRO-BIPHENYL-4-YL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-NITRO-BIPHENYL-4-YL)-ETHANONE(42771-77-7)
• EPA Substance Registry System: 1-(2-NITRO-BIPHENYL-4-YL)-ETHANONE(42771-77-7)

Safety Data

• Hazardous Substances Data: 42771-77-7(Hazardous Substances Data)

Usage

Uses

1-(2-Nitro[1,1''-biphenyl]-4-yl)ethanone is a useful reagent in the reductive cyclization of nitrobiphenyls and nitrostyrenes to carbazoles and indoles.

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 articles and documents

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.

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.

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.