852931-96-5

Basic information

• Product Name: 2-(2,6-dichlorobenzylidene)-3,4-dihydro-1(2H)-naphthalenone
• Synonyms: 2-(2,6-dichlorobenzylidene)-3,4-dihydro-1(2H)-naphthalenone
• CAS NO: 852931-96-5
• Molecular Formula: C17H12Cl2O
• Molecular Weight: 303.18258
• Mol File: 852931-96-5.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2,6-dichlorobenzylidene)-3,4-dihydro-1(2H)-naphthalenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,6-dichlorobenzylidene)-3,4-dihydro-1(2H)-naphthalenone(852931-96-5)
• EPA Substance Registry System: 2-(2,6-dichlorobenzylidene)-3,4-dihydro-1(2H)-naphthalenone(852931-96-5)

Safety Data

• Hazardous Substances Data: 852931-96-5(Hazardous Substances Data)

Upstream product

• 83-38-5 2,6-dichlorobenzaldehyde 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 

Relevant articles and documents

Tetralone derivatives are MIF tautomerase inhibitors and attenuate macrophage activation and amplify the hypothermic response in endotoxemic mice

Macrophage migration inhibitory factor (MIF) is a pro-inflammatory cytokine playing crucial role in immunity. MIF exerts a unique tautomerase enzymatic activity that has relevance concerning its multiple functions and its small molecule inhibitors have been proven to block its pro-inflammatory effects. Here we demonstrate that some of the E-2-arylmethylene-1-tetralones and their heteroanalogues efficiently bind to MIF’s active site and inhibit MIF tautomeric (enolase, ketolase activity) functions. A small set of the synthesised derivatives, namely compounds (4), (23), (24), (26) and (32), reduced inflammatory macrophage activation. Two of the selected compounds (24) and (26), however, markedly inhibited ROS and nitrite production, NF-κB activation, TNF-α, IL-6 and CCL-2 cytokine expression. Pre-treatment of mice with compound (24) exaggerated the hypothermic response to high dose of bacterial endotoxin. Our experiments suggest that tetralones and their derivatives inhibit MIF’s tautomeric functions and regulate macrophage activation and thermal changes in severe forms of systemic inflammation.