569646-59-9

Basic information

• Product Name: (2E)-1-(4-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one
• Synonyms: (2E)-1-(4-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one
• CAS NO: 569646-59-9
• Molecular Formula: C15H12ClNO
• Molecular Weight: 257.71488
• Mol File: 569646-59-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2E)-1-(4-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(4-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one(569646-59-9)
• EPA Substance Registry System: (2E)-1-(4-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one(569646-59-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 569646-59-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(2E)-1-(4-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one is used as a pharmaceutical intermediate for the development of drugs targeting various diseases due to its potential biological activities, including anti-inflammatory, antioxidant, and antitumor properties.
Used in Organic Synthesis:
(2E)-1-(4-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one is used as a valuable intermediate in the synthesis of more complex organic molecules, owing to its unique chemical structure and reactivity.

Upstream product

• 100-19-6 (4-nitrophenyl)ethanone 
• 104-88-1 4-chlorobenzaldehyde 
• 99-92-3 p-aminobenzophenone 
• 25870-65-9 3-(4-chlorophenyl)-1-(4-nitrophenyl)-2-propen-1-one 
• 114569-19-6 N-(4-Hydroxybenzyliden)-4-acetylanilin 
• 873-76-7 para-Chlorobenzyl alcohol 

Downstream Products

• 25870-88-6 1-(4-isothiocyanatophenyl)-3-(4-chlorophenyl)-2-propen-1-one 

Relevant articles and documents

Synthesis and studying of the biological activity of some new coumarin-3-Carboxylic acid heterocyclic derivatives

This study includes the synthesis of a few different coumarin-3-carboxylic acid derivatives of 1,2,3-triazole and triazoline as a starting material. The first step involves the formation of compound (a) in absolute ethanol through the reaction of coumarin

Design, synthesis, and evaluation of different scaffold derivatives against NS2B-NS3 protease of dengue virus

The number of deaths or critical health issues is a threat in the infection caused by Dengue virus, which complicates the situation, as only symptomatic treatment is the current solution. In this regard we have targeted the dengue protease NS2B-NS3 that is responsible for the replication. The series was designed with the help of molecular modeling approach using docking protocols. The series comprised of different scaffolds viz. cinnamic acid analogs (CA1–CA11), chalcone (C1–C10) and their molecular hybrids (Lik1–Lik10), analogs of benzimidazole (BZ1-BZ5), mercaptobenzimidazole (BS1-BS4), and phenylsulfanylmethylbenzimidazole (PS1-PS4). Virtual screening of various natural phytoconstituents was employed to determine the interactions of designed analogs with the residues of catalytic triad in the active site of NS2B-NS3. We have further synthesized the selected leads. The synthesized analogs were evaluated for the cytotoxicity and NS2B-NS3 protease inhibition activity and compared with known anti-dengue natural phytoconstituent quercetin as the standard. CA2, BZ1, and BS2 were found to be more potent and efficacious than the standard quercetin as evident from the protease inhibition assay.

A combined experimental and DFT investigation of mono azo thiobarbituric acid based chalcone disperse dyes

A number of monoazo dyes were synthesized by the reaction of 4-aminoacetophenone with different substituted benzaldehydes to give a new series of chalcone derivatives. The diazonium salts of these chalcones then allowed to react with thiobarbituric acid to produce the appropriate azo dye. The structures of the newly synthesized dyes were assigned by IR, NMR spectral data. IR study confirmed the existence of azo-dioxothioxo tautomer in the solid phase while 1H NMR study indicated the predominance of azoenol-oxothioxo or hydrazo-dioxothioxo tautomers. The geometries of the azo and hydrazo tautomeric forms and their electronic absorption of the dyes were optimized at B3LYP/6-311G level of theory. All the azo compounds were evaluated for their dyeing performance on polyester fibers, and PET. All the synthesized dyes gave moderate to excellent fastness properties on PET fiber. The effects of the nature of the substituents on the color and dyeing properties of these dyes have been evaluated. The mechanism of dyeing polyester fiber was discussed.

Synthesis and antiproliferative activity of chalcone-imide derivatives based on 3,4-dichloro-1h-pyrrole-2,5-dione

A series of chalcone imide derivatives,4'-aminochalcones-based dichloromaleimides,was synthesized from the reaction of 1-(4-acetylphenyl)-3,4-dichloro-1H-pyrrole-2,5-dione with various substituted aldehydes, or by treating 4'- aminochalcone with 3,4-dichlorofuran-2,5-dione in an alternative path. The structures of chalcone imide derivatives were established using IR, 1H NMR, 13C NMR, and mass spectroscopy. Antiproliferative effects of the newly synthesized compounds have been screened on two human cancer types via the MTT assay. Compounds with p-tolyl-1H-pyrrole-2,5-dione, and 4- bromophenyl-1H-pyrrole-2,5-dione derivatives, are highly active on the human liver cancer (HepG-2).On the other hand, all compounds were found to be more effective against breast cancer cells (MCF-7)than the positive control doxorubicin. The results of this work provide a basis for further research of selected chalcone-imide moiety as antiproliferative agents.

ADME properties, bioactivity and molecular docking studies of 4-amino-chalcone derivatives: new analogues for the treatment of Alzheimer, glaucoma and epileptic diseases

In this study, in vitro inhibition effects of (E)-1-(4-aminophenyl)-3-(aryl) prop-2-en-1-one (4-amino-chalcones) derivatives (3a–o) on acetylcholinesterase (AChE) enzyme and human erythrocyte carbonic anhydrase I and II isoenzymes (hCA I- II) were investigated. And also, the biological activities of 4-amino-chalcone derivatives against enzymes which names are acetylcholinesterase (PDB ID: 1OCE), human Carbonic Anhydrase I (PDB ID: 2CAB), human carbonic anhydrase II (PDB ID: 3DC3), were compared. After the results obtained, ADME/T analysis was performed in order to use 4-amino-chalcone derivatives as a drug in the future. Effective inhibitors of carbonic anhydrase I and II isozymes (hCAI and II) and acetylcholinesterase (AChE) enzymes with Ki values in the range of 2.55 ± 0.35–11.75 ± 3.57?nM for hCA I, 4.31 ± 0.78–17.55 ± 5.86?nM for hCA II and 96.01 ± 25.34–1411.41 ± 32.88?nM for AChE, respectively, were the 4-amino-chalcone derivatives (3a–o) molecules.

Design, synthesis and antibacterial activity of chalcones against MSSA and MRSA planktonic cells and biofilms

Staphylococcus aureus is the one of the most successful modern pathogens. The same bacterium that lives as a skin and mucosal commensal can be transmitted in health-care and community-settings and causes severe infections. Thus, there is a great challenge for a discovery of novel anti-Staphylococcus aureus compounds, which should act against resistant strains. Herein, we designed and synthesized a series of 17 chalcones, substituted by amino group on ring A, which were evaluated against methicillin-susceptible S. aureus (MSSA) and methicillin-resistant S. aureus MRSA planktonic cells. The antibacterial potency was improved by substituents on ring B, which were designed according to Topliss’ manual method. 4-bromo-3′-aminochalcone (5f) was the most active, demonstrating minimum inhibitory concentration (MIC) values of 1.9 μg mL?1 and 7.8 μg mL?1 against MSSA and MRSA, respectively. The association of 5f with vancomycin demonstrated synergistic effect against MSSA and MRSA, with Fractional Inhibitory Concentration Index (FICI) values of 0.4 and 0.3, respectively. Subinhibitory concentration of 5f inhibited the MSSA and MRSA adhesion to human keratinocytes. Chalcone 5f was able to reduce MSSA and MRSA biofilm formation, as well as acts on preformed biofilm in concentration-dependent mode. Scanning electron microscopy analyses confirmed severe perturbations caused by 5f on MSSA and MRSA biofilm architecture. The acute toxicity assay, using Galleria mellonella larvae, indicated a low toxic effect of 5f after 72 h, displaying lethality of 20% and 30% at 7.8 μg mL?1 and 78.0 μg mL?1, respectively. In addition, the antibacterial activity spectrum of 5f indicated action against planktonic cells of Enterococcus faecalis (MIC = 7.8 μg mL?1), Acinetobacter baumannii (MIC = 15.6 μg mL?1) and Mycobacterium tuberculosis (MIC = 5.7 μg mL?1). Altogether, these results open new avenues for 5f as an anti-Staphylococcus aureus agent, with potential applications as antibacterial drug, adjunct of antibiotics and medical devices coating.

Synthesis and biological activity of new chalcone scaffolds as prospective antimicrobial agents

Chalcones are open-chain flavonoids which contains two aromatic rings are joined by 3-carbons α-, β-unsaturated carbonyl chain. The, β-unsaturated ketonic group which is liable for the antimicrobial activity of the chalcone is additionally of vast use in

Aminophenyl chalcones potentiating antibiotic activity and inhibiting bacterial efflux pump

Chalcones and their derivatives are substances of great interest for medicinal chemistry due to their antibacterial activities. As the bacterial resistance to clinically available antibiotics has become a worldwide public health problem, it is essential to search for compounds capable of reverting the bacterial resistance. As a possibility, the chalcone class could be an interesting answer to this problem. The chalcones (2E)-1-(4′-aminophenyl)-3-(phenyl)?prop-2-en-1-one (APCHAL), and (2E)-1-(4′-aminophenyl)-3-(4-chlorophenyl)?prop-2-en-1-one (ACLOPHENYL) were synthesized by the Claisen-Schmidt condensation and characterized by 1H and 13C nuclear magnetic resonance (NMR), Fourier-transform infrared (FT-IR), and mass spectrometry (MS), In addition, microbiological tests were performed to investigate the antibacterial activity, modulatory potential, and efflux pump inhibition against Staphylococcus aureus (S. aureus) multi-resistant strains. Regarding the S. aureus Gram-positive model, the APCHAL presented synergism with gentamicin and antagonism with penicillin. APCHAL reduced the Minimum inhibitory concentration (MIC) of gentamicin by almost 70%. When comparing the effects of the antibiotic modifying activity of ACLOPHENYL and APCHAL, a loss of synergism is noted with gentamicin due to the addition of a chlorine to the substance structure. For Escherichia coli (E. coli) a total lack of effect, synergistic or antagonistic, was observed between ACLOPHENYL and the antibiotics. In the evaluation of inhibition of the efflux pump, both chalcones presented a synergistic effect with norfloxacin and ciprofloxacin against S. aureus, although the effect is much less pronounced with ACLOPHENYL. The effect of APCHAL is particularly notable against the K2068 (MepA overexpresser) strain, with synergistic effects with both ciprofloxacin and ethidium bromide. The docking results also show that both compounds bind to roughly the same region of the binding site of 1199B (NorA overexpresser), and that this region overlaps with the preferred binding region of norfloxacin. The APCHAL chalcone may contribute to the prevention or treatment of infectious diseases caused by multidrug-resistant S. aureus.

Novel potent and selective DPP-4 inhibitors: Design, synthesis and molecular docking study of dihydropyrimidine phthalimide hybrids

Background: Dipeptidyl peptidase-4 (DPP-4) inhibitors have emerged as antihyperglycemic agents that improve glycemic control in type 2 diabetic patients, either as monotherapy or in combination with other antidiabetic drugs. Methods: A novel series of dihydropyrimidine phthalimide hybrids was synthesized and evaluated for their in vitro and in vivo DPP-4 inhibition activity and selectivity using alogliptin as reference. Oral glucose tolerance test was assessed in type 2 diabetic rats after chronic treatment with the synthesized hybrids ± metformin. Cytotoxicity and antioxidant assays were performed. Additionally, molecular docking study with DPP-4 and structure activity relationship of the novel hybrids were also studied. Results: Among the synthesized hybrids, 10g, 10i, 10e, 10d and 10b had stronger in vitro DPP-4 inhibitory activity than alogliptin. Moreover, an in vivo DPP-4 inhibition assay revealed that 10g and 10i have the strongest and the most extended blood DPP-4 inhibitory activity compared to alogliptin. In type 2 diabetic rats, hybrids 10g, 10i and 10e exhibited better glycemic control than alogliptin, an effect that further supported by metformin combination. Finally, 10j, 10e, 10h and 10d had the highest radical scavenging activity in DPPH assay. Conclusions: Hybrids 10g, 10i and 10e are potent DPP-4 inhibitors which may be beneficial for T2DM treatment.

Design, synthesis, and anticancer activity studies of novel quinoline-chalcone derivatives

The chalcone and quinoline scaffolds are frequently utilized to design novel anticancer agents. As the continuation of our work on effective anticancer agents, we assumed that linking chalcone fragment to the quinoline scaffold through the principle of molecular hybridization strategy could produce novel compounds with potential anticancer activity. Therefore, quinoline-chalcone derivatives were designed and synthesized, and we explored their antiproliferative activity against MGC-803, HCT-116, and MCF-7 cells. Among these compounds, compound 12e exhibited a most excellent inhibitory potency against MGC-803, HCT-116, and MCF-7 cells with IC50 values of 1.38, 5.34, and 5.21 μM, respectively. The structure–activity relationship of quinoline-chalcone derivatives was preliminarily explored in this report. Further mechanism studies suggested that compound 12e inhibited MGC-803 cells in a dose-dependent manner and the cell colony formation activity of MGC-803 cells, arrested MGC-803 cells at the G2/M phase and significantly upregulated the levels of apoptosis-related proteins (Caspase3/9 and cleaved-PARP) in MGC-803 cells. In addition, compound 12e could significantly induce ROS generation, and was dependent on ROS production to exert inhibitory effects on gastric cancer cells. Taken together, all the results suggested that directly linking chalcone fragment to the quinoline scaffold could produce novel anticancer molecules, and compound 12e might be a valuable lead compound for the development of anticancer agents.