569646-61-3

Basic information

• Product Name: (2E)-1-(4-aminophenyl)-3-(4-methylphenyl)prop-2-en-1-one
• Synonyms: (2E)-1-(4-aminophenyl)-3-(4-methylphenyl)prop-2-en-1-one;(E)-1-(4-aminophenyl)-3-(4-methylphenyl)prop-2-en-1-one
• CAS NO: 569646-61-3
• Molecular Formula: C16H15NO
• Molecular Weight: 237.2964
• Mol File: 569646-61-3.mol
• Article Data: 26

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2E)-1-(4-aminophenyl)-3-(4-methylphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(4-aminophenyl)-3-(4-methylphenyl)prop-2-en-1-one(569646-61-3)
• EPA Substance Registry System: (2E)-1-(4-aminophenyl)-3-(4-methylphenyl)prop-2-en-1-one(569646-61-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 569646-61-3(Hazardous Substances Data)

Usage

General Description

The chemical "(2E)-1-(4-aminophenyl)-3-(4-methylphenyl)prop-2-en-1-one" is an organic compound that belongs to the class of enones. It is a yellow solid with a molecular formula of C15H15NO and a molecular weight of 221.29 g/mol. (2E)-1-(4-aminophenyl)-3-(4-methylphenyl)prop-2-en-1-one is commonly used as a building block in the synthesis of various organic and pharmaceutical compounds. It has potential applications in the pharmaceutical industry as a key intermediate in the production of drugs. The chemical structure of "(2E)-1-(4-aminophenyl)-3-(4-methylphenyl)prop-2-en-1-one" consists of a phenyl ring substituted with an amine group and a methyl group attached to a propenone moiety, giving it important chemical and biological properties.

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Downstream Products

• 25870-86-4 1-(4-isothiocyanatophenyl)-3-(4-methylphenyl)-2-propen-1-one 

Relevant articles and documents

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 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.

Synthesis and biological evaluation of amino chalcone derivatives as antiproliferative agents

Chalcone is a common scaffold found in many biologically active compounds. The chalcone scaffold was also frequently utilized to design novel anticancer agents with potent biological efficacy. Aiming to continue the research of effective chalcone derivatives to treat cancers with potent anticancer activity, fourteen amino chalcone derivatives were designed and synthesized. The antiproliferative activity of amino chalcone derivatives was studied in vitro and 5-Fu as a control group. Some of the compounds showed moderate to good activity against three human cancer cells (MGC-803, HCT-116 and MCF-7 cells) and compound 13e displayed the best antiproliferative activity against MGC-803 cells, HCT-116 cells and MCF-7 cells with IC50 values of 1.52 μM (MGC-803), 1.83 μM (HCT-116) and 2.54 μM (MCF-7), respectively which was more potent than the positive control (5-Fu). Further mechanism studies were explored. The results of cell colony formatting assay suggested compound 10e inhibited the colony formation of MGC-803 cells. DAPI fluorescent staining and flow cytometry assay showed compound 13e induced MGC-803 cells apoptosis. Western blotting experiment indicated compound 13e induced cell apoptosis via the extrinsic/intrinsic apoptosis pathway in MGC-803 cells. Therefore, compound 13e might be a valuable lead compound as antiproliferative agents and amino chalcone derivatives worth further effort to improve amino chalcone derivatives’ potency.