Chalcone

Chalcone is the organic compound C 6 H 5 C(O)CH=CHC 6 H 5 . It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids. They are widely known bioactive substances, fluorescent materials, and chemical intermediates.

Chalcone is the organic compound C 6 H 5 C(O)CH=CHC 6 H 5 . It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids. They are widely known bioactive substances, fluorescent materials, and chemical intermediates. ==Biosynthesis== Chalcones and chalconoids are synthesized in plants as secondary metabolites. The enzyme chalcone synthase, a type III polyketide synthase, is responsible for the biosynthesis of these compounds. The enzyme is found in all "higher" (vascular) and several "lower" (non-vascular) plants. ==Potential pharmacology== Chalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation. Some 2′-amino chalcones have been studied as potential antitumor agents. Chalcones are of interest in medicinal chemistry and have been described as a privileged scaffold. ==Uses== ===Medicinal uses=== In medicinal chemistry, chalcones have been used as: antioxidants anticancer agents antidiabetic drugs antiviral drugs antimalarial drugs ===Industrial uses=== In chemical industries, they are employed as: liquid crystals fluorescent chemical scaffolds metal sensors corrosion inhibitors plant hormones ===Uses in organic chemistry=== Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of pyrazoles and aurones. In the Johnson–Corey–Chaykovsky reaction, chalcone reacts with dimethylsulfoxonium methylide to give 1-phenyl-2-benzoylcyclopropane [15295-43-9] [1145-91-1] in 95% yield. A Leuckart reaction or ammonium acetate in the presence of sodium cyanoborohydride would be predicted to give Phenyl(2-phenylcyclopropyl)methanamine [1559116-96-9]. Alternatively if a reductive amination of the ketone with methylamine is performed one would instead get the secondary amine N-Me [1559367-56-4]. These compounds have the same trans-stereochemistry as was observed for tranylcypromine although their exact mode of pharmacology is still lacking. Lastly, it was discovered that if a hydrazine is prepared from the ketone (ala pheniprazine) one gets a compound that is called [Phenyl-(2-phenylcyclopropyl)methyl]hydrazine (PC105199424). ==See also== Juliá–Colonna epoxidation ==References== ==External links== Chalcone on reference.md

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