1017899-55-6

Basic information

• Product Name: 3-(4-FLUOROPHENYL)-1-(2,4,6-TRIMETHOXYPHENYL)-2-PROPEN-1-ONE
• Synonyms: 3-(4-FLUOROPHENYL)-1-(2,4,6-TRIMETHOXYPHENYL)-2-PROPEN-1-ONE;4-FLUORO-2',4',6'-TRIMETHOXYCHALCONE
• CAS NO: 1017899-55-6
• Molecular Formula: C18H17FO4
• Molecular Weight: 316.32
• Mol File: 1017899-55-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(4-FLUOROPHENYL)-1-(2,4,6-TRIMETHOXYPHENYL)-2-PROPEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-FLUOROPHENYL)-1-(2,4,6-TRIMETHOXYPHENYL)-2-PROPEN-1-ONE(1017899-55-6)
• EPA Substance Registry System: 3-(4-FLUOROPHENYL)-1-(2,4,6-TRIMETHOXYPHENYL)-2-PROPEN-1-ONE(1017899-55-6)

Safety Data

• Hazardous Substances Data: 1017899-55-6(Hazardous Substances Data)

Upstream product

• 403-42-9 1-(4-fluorophenyl)ethanone 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 459-57-4 4-fluorobenzaldehyde 

Relevant articles and documents

Trimethoxylated halogenated chalcones as dual inhibitors of mao-b and bace-1 for the treatment of neurodegenerative disorders

Six halogenated trimethoxy chalcone derivatives (CH1–CH6) were synthesized and spec-trally characterized. The compounds were further evaluated for their inhibitory potential against monoamine oxidases (MAOs) and β-secretase (BACE-1). Six compounds inhibit

Synthesis and biological evaluation of 3,5-diaryl-pyrazole derivatives as potential antiprostate cancer agents

Prostate cancer is the most frequently diagnosed tumor in men and the second leading cause of cancer-associated mortality in most developed countries. 3,5-Diaryl substituted pyrazole derivatives (20–28) were prepared starting from related chalcones and bi

Design, synthesis and antiproliferative activity evaluation of fluorine-containing chalcone derivatives

A series of new chalcones containing fluoro atom at B ring have been designed, synthesized, and evaluated to be antiproliferative activity against a panel of human tumor cell lines. Some of the analogs (8, 9, 12, 45, 46 and 48) displayed powerful antiproliferative effects to certain human tumor cells, but all of them were devoid of any cytotoxicity towards the normal HEK 293. Acridine orange staining data supported that the cytotoxic and antiproliferative effects of the synthesized analogs on tumor cells are mediated through apoptosis. The compounds 12 and 46 manifested concentration-dependent antiproliferative activity in human hepatocellular carcinoma cell lines using an xCELLigence assay. The structures and antiproliferative activity relationship were further supported by in silico molecular docking study of the compounds against tubulin protein which suggests our compounds interference to cell division. Communicated by Ramaswamy H. Sarma.

Design, synthesis and biological evaluation of 3,5-diaryl isoxazole derivatives as potential anticancer agents

The present study was carried out in the attempt to synthesize a new class of potential anticancer agents comprising eleven compounds (24–34) sharing the 3,5-diarylisoxazole as a core. The chemical structure of the new synthesized compounds was established by IR, 1H NMR, 13C NMR and elemental analysis. Their biological potential towards prostate cancer was evaluated by using cancer PC3 cells and non-tumorigenic PNT1a cells. Interestingly, compound 26 distinguished from others with a quite high selectivity value that is comparable to 5-FU. The binding mode of 26 towards Ribosomal protein S6 kinase beta-1 (S6K1) was investigated at a molecular level of detail by employing docking simulations based on GLIDE standard precision as well as MM-GBSA calculations.

Mechanisms of action and structure-activity relationships of cytotoxic flavokawain derivatives

22 Flavokawain derivatives (FKd) were obtained by one step syntheses in order to conduct a SAR study to understand the structural requirements for optimum and selective cytotoxicity. FKd and natural flavokawains A and B found into kava, a South Pacific traditional beverage, were evaluated against nine cancer and one healthy cell lines. The targeted cell cycle phases as well as the effects on the induction of apoptosis and cell cycle protein levels were investigated. Therapeutic improvements (more activity and selectivity) were achieved with FKd compared to natural flavokawains and notably with the 2′,3,4′,6′-tetramethoxychalcone (FKd 19). FKd induced a G1/S arrest on p53 wild-type cells and an M arrest on p53 mutant-type, via the up-regulation of p21 and cyclin B1 proteins, followed by apoptosis. Moreover, FKd exhibited a 24?h-effect on Akt/mTor normal cells versus a 48?h-effect on Akt/mTor up-regulated cells. The SAR study resulted in the conclusion that trimethoxy A-ring allowed the best compromise between cytotoxicity and selectivity, as well as the substitution of the meta position on the B-ring and the use of halogens substituents.

Design of potent fluoro-substituted chalcones as antimicrobial agents

Owing to ever-increasing bacterial and fungal drug resistance, we attempted to develop novel antitubercular and antimicrobial agents. For this purpose, we developed some new fluorine-substituted chalcone analogs (3, 4, 9–15, and 20–23) using a structure–a

Enantioselective Ring Opening of meso-Epoxides with Silicon Tetrachloride Catalyzed by Pyridine N-Oxides Fused with the Bicyclo[3.3.1]nonane Framework

The synthesis of new chiral Lewis basic organocatalysts that contain pyridine N-oxide moieties fused with the bicyclo[3.3.1]nonane framework is reported. The obtained pyridine N-oxides were employed as catalysts in the enantioselective ring opening of meso-epoxides with silicon tetrachloride. Derivative 1b endowed with two 2,4-diaryl-substituted pyridine N-oxide moieties proved to be a particularly effective catalyst for desymmetrization of norbornene oxide 16i to furnish Wagner-Meerwein rearrangement product 20i in unprecedented 96 % ee. Difunctional congener 3, which is striped of the 4-aryl substituents, exhibited moderate to high levels of asymmetric induction (47-88 % ee) with alicyclic epoxide substrates. Chiral Lewis basic catalysts with pyridine N-oxide moieties fused with a bicyclo[3.3.1]nonane framework were used in the enantioselective ring opening of meso-epoxides. 2,4-Diaryl-substituted N-oxide exhibited excellent asymmetric induction with norbornene oxide (96 % ee), whereas less-substituted congener was most effective with alicyclic epoxide substrates (47-88 % ee).