616232-04-3

Basic information

• Product Name: (2E)-1-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
• Synonyms: (2E)-1-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one;(E)-1-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
• CAS NO: 616232-04-3
• Molecular Formula: C₁₇H₁₇NO₃
• Molecular Weight: 283.32178
• Mol File: 616232-04-3.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2E)-1-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one(616232-04-3)
• EPA Substance Registry System: (2E)-1-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one(616232-04-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 616232-04-3(Hazardous Substances Data)

Usage

General Description

The chemical (2E)-1-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one, also known as "Curcumin analog C1" is a synthetic compound with potential biological activities. It is a curcumin analog, a derivative of the natural compound curcumin found in the turmeric plant. Studies have shown that curcumin analog C1 exhibits anti-inflammatory, antioxidant, and anticancer properties. It has also been found to inhibit the growth of cancer cells and possess potential therapeutic benefits for various diseases. The compound's structure contains an amino group, a dimethoxyphenyl group, and a prop-2-en-1-one group, which are believed to contribute to its biological activities. Due to its promising properties, curcumin analog C1 is a subject of ongoing research for potential pharmaceutical applications.

Upstream product

• 99-92-3 p-aminobenzophenone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 1352346-96-3 (E)-3-(3,4-dimethoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one 

Downstream Products

• 1151741-90-0 2-bromo-N-(4-((E)-3-(3,4-dimethoxyphenyl)acryloyl)phenyl)acrylamide 

Relevant articles and documents

Acryloylphenylcarboxamides: A New Class of Breast Cancer Resistance Protein (ABCG2) Modulators

Chalcones are easily synthesized natural precursors of secondary plant metabolites, and their derivatives show various biological activities including inhibition of ABC transporters. Especially, their role as inhibitors of ABCG2, the most recently discovered ABC transporter involved in multidrug resistance, inspired the synthesis of new structurally diverse derivatives. Therefore, we combined the typical chalcone moiety with several acid chlorides by using an amide linker at position 2′, 3′, or 4′ on ring A of the chalcone. The resulting 35 compounds covered a wide spectrum of substitution patterns, which allowed development of structure–activity relationships and to find the optimal structural features for further investigations. Synthesized acryloylphenylcarboxamides were investigated for their inhibitory activity against ABCG2 and their behavior toward ABCB1 and ABCC1. Furthermore, for the most promising compounds, their intrinsic cytotoxicity and their ability to reverse ABCG2-mediated multidrug resistance were determined.

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 neuroprotective effects of novel chalcone-triazole hybrids

The development of novel neuroprotective agents is urgently needed for the treatment of neurodegenerative diseases, affecting aging individuals worldwide. In this study, a new set of chalcone-triazole hybrids (6a-g) was synthesized and evaluated for their