342808-40-6

Basic information

• Product Name: 3,5-Bis[(2-fluorophenyl)Methylene]-4-piperidinone
• Synonyms: 3,5-Bis[(2-fluorophenyl)Methylene]-4-piperidinone;(3E,5E)-3,5-bis[(2-fluorophenyl)methylene]-4-piperidinone;EF-24
• CAS NO: 342808-40-6
• Molecular Formula: C₁₉H₁₅F₂NO
• Molecular Weight: 311.3253064
• Product Categories: Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 342808-40-6.mol
• Article Data: 9

Chemical Properties

• Appearance: yellow/
• Storage Temp.: ?20°C
• Solubility: DMSO: ≥10mg/mL
• CAS DataBase Reference: 3,5-Bis[(2-fluorophenyl)Methylene]-4-piperidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Bis[(2-fluorophenyl)Methylene]-4-piperidinone(342808-40-6)
• EPA Substance Registry System: 3,5-Bis[(2-fluorophenyl)Methylene]-4-piperidinone(342808-40-6)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50
• Safety Statements: 61
• WGK Germany: 3
• Hazardous Substances Data: 342808-40-6(Hazardous Substances Data)

Usage

Uses

3,5-Bis[(2-fluorophenyl)methylene]-4-piperidinone is an analog of curcumin that acts as a kinase inhibitor which mediates anticancer properties.

Upstream product

• 1217237-15-4 3,5-bis(2-fluorobenzylidene)-4-piperidone hydrochloride 
• 342808-41-7 3,5-bis-(2-fluorobenzylidene)-4-piperidone acetic acid 
• 41979-39-9 4-piperidone hydrochloride 
• 446-52-6 2-Fluorobenzaldehyde 
• 41661-47-6 piperidin-4-one 
• 342808-24-6 3,5-bis(2-pyridinylmethylidene)-4-piperidone 

Downstream Products

• 600637-08-9 4-[3,5-bis(2-fluorobenzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butanoic acid 
• 896743-51-4 5-[3,5-bis-(2-fluorobenzylidene)-4-oxopiperidin-1-yl]-5-oxopentanoic acid 
• 1246964-13-5 3,5-bis(2-fluorobenzyl)-4-piperidone 
• 939343-12-1 N-acetyl-3,5-bis(2-fluorobenzylidene)-4-piperidone 
• 1437707-98-6 C₂₀H₁₇F₂N₃O 

Relevant articles and documents

Anti-inflammatory activity of ortho-trifluoromethoxy-substituted 4-piperidione-containing mono-carbonyl curcumin derivatives in vitro and in vivo

Curcumin was reported as an anti-inflammatory agent. However, curcumin's poor bioavailability limited its clinical utility. Here, thirty ortho-substituted mono-carbonyl curcumin derivatives, containing acetone, cyclopentanone, cyclohexanone or 4-piperidione (N—H, N-methyl or N-acrylyl) moieties replacing β-diketone moiety of curcumin, were investigated for anti-inflammatory activity. Two active ortho-trifluoromethoxy-substituted 4-piperidione-containing derivatives 22 and 24 owned good cell uptake ability, and displayed excellent anti-inflammatory activity in both lipopolysaccharide-induced Raw264.7 macrophages and a dextran sulfate sodium (DSS)-induced mouse model of colitis. They inhibited the production of nitric oxide, reactive oxygen species, malonic dialdehyde and cyclooxygenase-2; and the expression of pro-inflammatory cytokines interleukin-1β, tumor necrosis factor-α and myeloperoxidase; the phosphorylation of mitogen-activated protein kinases; and the nucleus translocation of p65. What's more, 22 or 24 oral administered reduced the severity of clinical symptoms of ulcerative colitis (body weight and disease activity index), and reduced obviously DSS-induced colonic pathological damage (the colon length and histopathology analysis). These results suggested that ortho-trifluoromethoxy-substituted 4-piperidione-containing mono-carbonyl curcumin derivatives 22 and 24 were potential anti-inflammatory agents; and offered the important information for design and discovery of more potent anti-inflammatory drug candidates.

3,5-Bis(2-fluorobenzylidene)-4-piperidone induce reactive oxygen species-mediated apoptosis in A549 cells

The presence of the substituents in the ortho position of the aromatic ring(s) is helpful to strenghen the biological activity, highlighting a so-called ortho effect. In this paper, we synthesized six mono-carbonyl curcumin analogs with the fluorine group

Synthesis and discovery of highly functionalized mono- and bis-spiro-pyrrolidines as potent cholinesterase enzyme inhibitors

Novel mono and bis spiropyrrolidine derivatives were synthesized via an efficient ionic liquid mediated, 1,3-dipolar cycloaddition methodology and evaluated in vitro for their AChE and BChE inhibitory activities in search for potent cholinesterase enzyme