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.

Upstream product

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Downstream Products

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Relevant articles and documents

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.

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.