53744-32-4

Basic information

• Product Name: (2E)-1-(2-nitrophenyl)-3-phenyl-2-propen-1-one
• Synonyms: (2E)-1-(2-nitrophenyl)-3-phenyl-2-propen-1-one
• CAS NO: 53744-32-4
• Molecular Weight: 253.257
• Mol File: 53744-32-4.mol

Chemical Properties

• CAS DataBase Reference: (2E)-1-(2-nitrophenyl)-3-phenyl-2-propen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(2-nitrophenyl)-3-phenyl-2-propen-1-one(53744-32-4)
• EPA Substance Registry System: (2E)-1-(2-nitrophenyl)-3-phenyl-2-propen-1-one(53744-32-4)

Safety Data

• Hazardous Substances Data: 53744-32-4(Hazardous Substances Data)

Upstream product

• 577-59-3 2-acetylnitrobenzene 
• 100-52-7 benzaldehyde 
• 581-55-5 benzylidene 1,1-diacetate 

Downstream Products

• 78807-66-6 2-[5-(2-Nitro-phenyl)-3-phenyl-4,5-dihydro-pyrazol-1-yl]-1-phenothiazin-10-yl-ethanone 
• 16619-14-0 2-phenyl-2,3-dihydro-1H-quinolin-4-one 
• 14802-18-7 2-phenyl-1H-quinolin-4-one 
• 726208-00-0 (E)-2-(3-oxoindolin-2-ylidene)-2-phenylacetonitrile 

Relevant articles and documents

Promising Non-cytotoxic Monosubstituted Chalcones to Target Monoamine Oxidase-B

A library of monosubstituted chalcones (1-17) bearing electron-donating and electron-withdrawing groups on both aromatic rings were selected. The cell viability on human tumor cell lines was evaluated first. The compounds unable to induce detectable cytotoxicity (1, 13, and 14) were tested using the monoamine oxidase (MAO) activity assay. Interestingly, they inhibit MAO-B, acting as competitive inhibitors, with 13 and 14 showing the best profiles. In particular, 13 exhibited a potency higher than that of safinamide, taken as a reference. Docking studies and crystallographic analysis showed that in human MAO-B 13 binds with the halogen-substituted aromatic ring in the entrance cavity, similar to safinamide, whereas 14 is accommodated in the opposite way. The main conclusion of this cell biology, biochemistry, and structural study is to highlights 13 as a chalcone derivative that is worth consideration for the development of novel MAO-B-selective inhibitors for the treatment of neurodegenerative diseases.

Unexpected cyclization ofortho-nitrochalcones into 2-alkylideneindolin-3-ones

An original, facile, and highly efficient method for the preparation of 2-(3-oxoindolin-2-ylidene)acetonitriles fromortho-nitrochalcones is described. The featured transformation is a triggered Michael addition of the cyanide anion to the chalcone followed by a cascade cyclization mechanistically related to the Baeyer-Drewson reaction.

Antiproliferative effects of chalcones on T cell acute lymphoblastic leukemia-derived cells: Role of PKCβ

In this study, a series of 20 chalcone derivatives was synthesized, and their antiproliferative activity was tested against the human T cell acute lymphoblastic leukemia-derived cell line, CCRF-CEM. On the basis of the structural features of the most active compounds, a new library of chalcone derivatives, according to the structure–activity relationship design, was synthesized, and their antiproliferative activity was tested against the same cancer cell line. Furthermore, four of these derivatives (compounds 3, 4, 8, 28), based on lower IC50 values (between 6.1 and 8.9 μM), were selected for further investigation regarding the modulation of the protein expression of RACK1 (receptor for activated C kinase), protein kinase C (PKC)α and PKCβ, and their action on the cell cycle level. The cell cycle analysis indicated a block in the G0/G1 phase for all four compounds, with a statistically significant decrease in the percentage of cells in the S phase, with no indication of apoptosis (sub-G0/G1 phase). Compounds 4 and 8 showed a statistically significant reduction in the expression of PKCα and an increase in PKCβ, which together with the demonstration of an antiproliferative role of PKCβ, as assessed by treating cells with a selective PKCβ activator, indicated that the observed antiproliferative effect is likely to be mediated through PKCβ induction.

Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties

The three-component reaction between alkyl- or arylamines, β-ketoesters and chalcones in refluxing ethanol containing a catalytic amount of Ce(IV) ammonium nitrate allowed the construction of a large library of highly substituted dihydro-m-terphenyl derivatives containing β-alkylamino- or β-arylamino ester moieties. This process generates three new bonds and one ring and proceeds in high atom economy, having two molecules of water as the only side product. Another domino process, in which the original MCR was telescoped with a subsequent aza Michael/retro-aza Michael sequence, allowed the one-pot preparation of a library of compounds with a N-unsubstituted β-aminoester fragment. Finally, to extend the structural diversity of these libraries, we also examined the aromatization of the central ring of our compounds in the presence of dichlorodicyanoquinone. This reaction sequence did not affect the integrity of a stereogenic center belonging to the amino component.

One-Pot Synthesis of Functionalized Carbazoles via a CAN-Catalyzed Multicomponent Process Comprising a C-H Activation Step

The microwave-promoted three-component reaction between o-nitrochalcones, primary amines and β-dicarbonyl compounds in the presence of Ce(IV) ammonium nitrate constitutes the first example of a multicomponent carbazole synthesis. This reaction furnishes highly substituted and functionalized carbazole derivatives via a double annulation process that generates two C-C and two C-N bonds, with water as the only side product. Mechanistically, this transformation has some unusual features that include an intramolecular coupled hydrogenation-dehydrogenation process, the functionalization of a C-H group by direct attack onto a nitrogen function and a CAN-catalyzed reduction via hydride transfer from ethanol. The mechanisms of these reactions were studied with the aid of computational techniques.

Process Intensification with Bifunctional Heterogeneous Catalysts: Selective One-Pot Synthesis of 2′-Aminochalcones

(Chemical Equation Presented) 2′-Aminochalcones of pharmaceutical and commercial interest have been obtained in high yields and selectivities through a one-pot process using a bifunctional heterogeneous catalyst bearing base and metal active sites. This is a physical mixture material formed by a high-surface-area MgO and Pt on TiO2. The process involves as the first step the Claisen-Schmidt condensation between o-nitroacetophenone and benzaldehyde derivatives on the basic catalytic function. This is followed by a chemoselective hydrogenation of the nitro group in the presence of the carbonyl and double-bond carbon-carbon groups within the molecule. Using the bifunctional catalyst and the reaction system proposed here, it is possible to produce, under mild reaction conditions and short reaction times, 2′-aminochalcones with higher yields and selectivities than those obtained by conventional multistep methods.

Synthesis and anti-inflammatory activity of three nitro chalcones

The aim of this study was to synthesize three nitro substituted chalcones and to evaluate their anti-inflammatory activity in the model of carrageenan induced edema in rats. The nitro chalcone were prepared by aldol condensation using of mechanical agitation and environmentally friendly solvents with 72-73% yields in approximately 2 h. The three structures were evaluated on biological activity at dose of 200 mg/kg and they showed anti-inflammatory protective effect by both oral and intraperitoneal administration, this effect was time dependent.

(±)-2-Aryl-2,3-dihydro-4(1H)-quinolinones by a tandem reduction-Michael addition reaction

An efficient synthesis of (±)-2-aryl-2,3-dihydro-4(1H)-quinolinones has been developed from chalcones prepared from 2′-nitroacetophenone and a series of substituted benzaldehydes. The cyclization sequence is initiated by reduction of the nitro group under dissolving metal conditions using iron powder in concentrated hydrochloric acid. Milder conditions, using acetic acid or acetic acid-phosphoric acid as the reaction medium, were less satisfactory. Procedural details as well as a mechanistic discussion and reaction optimization studies are presented.

Screening of biological activities of a series of chalcone derivatives against human pathogenic microorganisms

In an effort to develop new antimicrobial agents, a series of chalcone derivatives, 3-60, were prepared by Claisen-Schmidt condensation of appropriate acetophenones and 2-furyl methyl ketones with appropriate aromatic aldehydes, furfural, and thiophene-2-carbaldehyde in an aqueous solution of NaOH and EtOH at room temperature. The synthesized compounds were characterized by means of their IR- and NMR-spectral data, and elemental analysis. All compounds were tested for their antibacterial and antifungal activities by the disc diffusion method. For the most active compounds, also minimum inhibitory concentrations (MICs) were determined.

Application of the Pictet-Spengler reaction to aryl amine-based substrates having pyrimidine as a π-nucleophile: synthesis of pyrimidoquinolines with structural analogy to benzonaphthyridines present in alkaloids

Synthesis of pyrimidine annulated quinolines, structurally analogous to biologically active benzonaphthyridines present in alkaloids, has been described. Our synthetic strategy is based on the modified Pictet-Spengler reaction involving substrates comprising deactivated pyrimidine ring as the nucleophilic partner whereas aryl amine originating from the C-4 of the pyrimidine ring served as the source for electrophilic partner. The resulting substrates 5-7 with diversity at 2- and 6-position after condensation with a variety of aldehydes underwent 6-endo cyclization to furnish pyrimido[5,4-c]quinolines 14 in good yields. However, attempts to further extend this strategy on new structurally analogous substrate involving the pyridine ring as nucleophilic partner failed, thus limiting the scope of the reaction.