1037642-78-6

Basic information

• Product Name: (2E)-1-(4-aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• Synonyms: (2E)-1-(4-aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one;(E)-1-(4-aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS NO: 1037642-78-6
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.34776
• Mol File: 1037642-78-6.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2E)-1-(4-aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(4-aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(1037642-78-6)
• EPA Substance Registry System: (2E)-1-(4-aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(1037642-78-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1037642-78-6(Hazardous Substances Data)

Usage

General Description

The chemical (2E)-1-(4-aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one is a compound with the molecular formula C18H19NO4. It is a yellow crystalline powder with a molecular weight of 313.35 g/mol. (2E)-1-(4-aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one is a derivative of 1-phenyl-2-propen-1-one and contains both an amino group and three methoxy groups attached to a phenyl group. It has potential applications in pharmaceutical research and drug development due to its structural features and reactivity. Additionally, it may also have uses in organic synthesis and as a building block for the creation of other complex chemical compounds. Overall, this chemical compound has the potential for various applications in the fields of chemistry and pharmacology.

Upstream product

• 1103585-01-8 (E)-3-(3,4,5-trimethoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 99-92-3 p-aminobenzophenone 

Downstream Products

• 1151741-96-6 2-bromo-N-(4-((E)-3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)acrylamide 
• 127033-84-5 4-acetamido-3',4',5'-trimethoxychalcone 
• 1621674-93-8 (E)-4-((1-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2H-chromen-2-one 
• 1621674-88-1 (E)-7-((1-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2H-chromen-2-one 
• 1621674-82-5 (E)-1-(4-azidophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 

Relevant articles and documents

In vitro antioxidant activity and scavenging effects of some synthesized 4-Aminochalcones

A new series of substituted 4'-aminochalcones were synthesized by Claisen-Schmidt condensation of 4-aminoacetophenone with various substituted aromatic/heteroaromatic aldehydes. The antioxidant activity for all these compounds were studied on various reac

Novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids: Synthesis, physicochemical properties, anticancer and topoisomerase i and II inhibitory activity

A group of novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids was prepared. One-dose anticancer test results indicated that compounds 3a and 3g exhibited the highest ability to inhibit the proliferation of different cancer cell lines. Compound 3a exhibited a broad-spectrum of anti-tumor activity without pronounced selectivity while compound 3g revealed high selectivity toward the leukemia subpanel with selectivity ratio of 6.71 at GI50 level. Moreover, compounds 3e and 3j have shown remarkable topo II inhibitory activity compared to etoposide at 100 μM and 20 μM concentrations. Compounds 3e and 3j exhibited comparably potent topo I inhibitory activity at 20 μM concentration compared to camptothecin. Compounds 3e and 3j exhibited strong topo II inhibitory activities compared to topo I at 20 μM concentration. Studying of the solubility and partition coefficient revealed higher lipophilicity of the hybrids 3a-j compared to the parent ciprofloxacin.

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.