5452-98-2

Usage

Uses

Used in Pharmaceutical Synthesis:
(2E)-1-(2,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one is used as an intermediate in the synthesis of pharmaceuticals. It serves as a key building block for the development of various drugs due to its unique chemical structure and properties.
Used in Antioxidant Applications:
In various plant sources, (2E)-1-(2,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one exhibits antioxidant properties. It helps protect cells from oxidative damage caused by free radicals, contributing to the maintenance of overall health and well-being.
Used in Antimicrobial Applications:
This chalcone compound also demonstrates antimicrobial properties, making it useful in the development of antimicrobial agents. It can be employed to combat various types of bacteria and other microorganisms, contributing to the prevention and treatment of infections.
Used in Anticancer Applications:
(2E)-1-(2,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one has been found to possess anticancer properties. It can be used in the development of cancer treatments, potentially targeting and inhibiting the growth of cancer cells, and offering a promising avenue for cancer therapy research.

Upstream product

• 2040-04-2 2,6-dimethoxyacetophenone 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

A synthetic chalcone as a potent inducer of glutathione biosynthesis

Chalcones continue to attract considerable interest due to their anti-inflammatory and antiangiogenic properties. We recently reported the ability of 2′,5′-dihydroxychalcone (2′,5′-DHC) to induce both breast cancer resistance protein-mediated export of glutathione (GSH) and c-Jun N-terminal kinase-mediated increased intracellular GSH levels. Herein, we report a structure-activity relationship study of a series of 30 synthetic chalcone derivatives with hydroxyl, methoxyl, and halogen (F and Cl) substituents and their ability to increase intracellular GSH levels. This effect was drastically improved with one or two electrowithdrawing groups on phenyl ring B and up to three methoxyl and/or hydroxyl groups on phenyl ring A. The optimal structure, 2-chloro-4′,6′-dimethoxy-2′- hydroxychalcone, induced both a potent NF-E2-related factor 2-mediated transcriptional response and an increased formation of glutamate cysteine ligase holoenzyme, as shown using a human breast cancer cell line stably expressing a luciferase reporter gene driven by antioxidant response elements.

Investigation of chalcones as selective inhibitors of the breast cancer resistance protein: Critical role of methoxylation in both inhibition potency and cytotoxicity

ABCG2 plays a major role in anticancer-drug efflux and related tumor multidrug resistance. Potent and selective ABCG2 inhibitors with low cytotoxicity were investigated among a series of 44 chalcones and analogues (1,3-diarylpropenones), by evaluating their inhibitory effect on the transport of mitoxantrone, a known ABCG2 substrate. Six compounds producing complete inhibition with IC50 values below 0.5 μM and high selectivity for ABCG2 were identified. The number and position of methoxy substituents appeared to be critical for both inhibition and cytotoxicity. The best compounds, with potent inhibition and low toxicity, contained an N-methyl-1-indolyl (compound 38) or a 6′-hydroxyl-2′,4′-dimethoxy-1-phenyl (compound 27) moiety (A-ring) and two methoxy groups at positions 2 and 6 of the 3-phenyl moiety (B-ring). Methoxy substitution contributed to inhibition at positions 3 and 5, but had a negative effect at position 4. Finally, methoxy groups at positions 3, 4, and 5 of the B-ring markedly increased cytotoxicity and, therefore, should be avoided.

NUCLEAR RECEPTOR MODULATORS AND THEIR USE FOR THE TREATMENT AND PREVENTION OF CANCER

Disclosed are compounds which are nuclear receptor modulators that can act as antagonists to the androgen receptor, for example, a compound of Formula I: wherein R1 to R5 and X1 to X5 are as described herein, as well as pharmaceutically acceptable salts, solvates, and stereoisomers thereof. Pharmaceutical compositions comprising such compounds, as well as methods of use, and treatment for cancers, including prostate cancers, other nuclear receptor mediated cancers, and other conditions, are also disclosed.