108979-08-4

Basic information

• Product Name: 2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)-
• CAS NO: 108979-08-4
• Molecular Formula: C17H15BrO4
• Molecular Weight: 363.208
• Mol File: 108979-08-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)-(108979-08-4)
• EPA Substance Registry System: 2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)-(108979-08-4)

Safety Data

• Hazardous Substances Data: 108979-08-4(Hazardous Substances Data)

Usage

Description

2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)is a chemical compound that consists of a propenone group attached to a phenyl group with a bromine atom and another phenyl group with hydroxyl and dimethoxy substituents. It is a ketone with a double bond and is commonly used in organic synthesis and as a flavoring agent in the food industry. The presence of bromine and hydroxyl groups in its structure makes it potentially useful for medicinal and pharmaceutical applications. Additionally, the dimethoxy substituents provide the compound with antioxidant properties, making it potentially beneficial for health and skincare products.

Uses

Used in Organic Synthesis:
2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)is used as a building block in organic synthesis for the creation of various chemical compounds.
Used in Flavoring Agents:
2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)is used as a flavoring agent in the food industry to impart unique flavors to food products.
Used in Medicinal and Pharmaceutical Applications:
2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)is used as a potential candidate for medicinal and pharmaceutical applications due to the presence of bromine and hydroxyl groups in its structure.
Used in Health and Skincare Products:
2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)is used in health and skincare products due to its antioxidant properties provided by the dimethoxy substituents.

Upstream product

• 871878-99-8 1-(2,4-dimethoxyphenyl)-2-hydroxyethanone 
• 1122-91-4 4-bromo-benzaldehyde 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 108-73-6 3,5-dihydroxyphenol 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 99-90-1 para-bromoacetophenone 

Downstream Products

• 3791-76-2 2’-hydroxy-4’,6’-dimethoxydihydrochalcone 
• 350982-89-7 (Z)-2-(4-bromobenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one 
• 1394173-49-9 C₁₇H₁₄Br₂O₄ 

Relevant articles and documents

Targeting the MDM2-p53 protein-protein interaction with prenylchalcones: Synthesis of a small library and evaluation of potential antitumor activity

Prenylation of several bioactive scaffolds is a very interesting strategy used in Medicinal Chemistry in order to improve biological/pharmacological effects. A small library of prenylchalcones was synthesized and evaluated for the ability to inhibit the MDM2-p53 interaction using a yeast-based assay. The capacity of all synthesized prenylchalcones and their non-prenylated precursors to inhibit the growth of human colon tumor HCT116 cells was also evaluated. The obtained results led to the identification of a hit compound, prenylchalcone 2e, which behaved as potential inhibitor of the MDM2-p53 interaction in yeast, and showed improved cytotoxicity against human tumor cells expressing wild-type p53, including liver hepatocellular carcinoma HepG2, breast adenocarcinoma MCF-7, and malignant melanoma A375 cells. In colon cancer cells, it was also shown that the growth inhibitory effect of prenylchalcone 2e was associated with the induction of cell cycle arrest, apoptosis, and increased protein expression levels of p53 transcriptional targets. Moreover, computational docking studies were performed in order to predict docking poses and residues involved in the MDM2-p53 potential interaction.

Development of a novel nitric oxide (NO) production inhibitor with potential therapeutic effect on chronic inflammation

Inflammation is a complex biological response to stimuli. Activated macrophages induced excessively release of pro-inflammatory cytokines and mediators such as endogenous radical nitric oxide (NO) play a significant role in the progression of multiple inflammatory diseases. Both natural and synthetic chalcones possess a wide range of bioactivities. In this work, thirty-nine chalcones and three related compounds, including several novel ones, based on bioactive kava chalcones were designed, synthesized and their inhibitory effects on NO production in RAW 264.7 cells were evaluated. The novel compound (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3-methoxy-4-(3-morpholinopropoxy)phenyl)prop-2-en-1-one (53) exhibited a better inhibitory activity (84.0%) on NO production at 10 μM (IC50 = 6.4 μM) with the lowest cytotoxicity (IC50 > 80 μM) among the tested compounds. Besides, western blot analysis indicated that compound 53 was a potent down-regulator of inducible nitric oxide synthase (iNOS) protein. Docking study revealed that compound 53 also can dock into the active site of iNOS. Furthermore, at the dose of 10 mg/kg/day, compound 53 could both significantly suppress the progression of inflammation on collagen-induced arthritis (CIA) and adjuvant-induced arthritis (AIA) models. In addition, the structure-activity relationship (SAR) of the kava chalcones based analogs was also depicted.

In Vitro and in Vivo Antischistosomal Activities of Chalcones

In this study, we evaluated the in vitro and in vivo schistosomicidal activities of chalcones against Schistosoma mansoni worms. In vitro assays revealed that chalcones 1 and 3 were the most active compounds, without affecting significantly mammalian cells. Confocal laser scanning microscopy and scanning electron microscopy studies revealed reduction on the numbers of tubercles and morphological alterations in the tegument of S. mansoni worms after in vitro incubation with chalcones 1 and 3. In a mouse model of schistosomiasis, the oral treatment (400 mg/kg) with chalcone 1 or 3 significantly caused a total worm burden reduction in mice. Chalcone 1 showed significant inhibition of the S. mansoni ATP diphosphohydrolase activity, which was corroborated by molecular docking studies. The results suggested that chalcones could be explored as lead compounds with antischistosomal properties.