Chalcone
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| Names | |
|---|---|
| IUPAC name
1,3-Diphenyl-2-propen-1-one | |
| Other names
Chalcone Chalkone Benzylideneacetophenone Phenyl styryl ketone | |
| Identifiers | |
94-41-7  614-47-1 ((E)-Chalcone)  | |
| ChEBI | CHEBI:27618 |
| ChemSpider | 6921 |
| Jmol interactive 3D | Image |
| PubChem | 637760 |
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| Properties | |
| C15H12O | |
| Molar mass | 208.26 g/mol |
| Density | 1.071 g/cm3 |
| Melting point | 55 to 57 °C (131 to 135 °F; 328 to 330 K) |
| Boiling point | 345 to 348 °C (653 to 658 °F; 618 to 621 K) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
Chalcone is an aromatic ketone and an enone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones or chalconoids. Benzylideneacetophenone is the parent member of the chalcone series. The alternative name given to chalcone are phenyl styryl ketone, benzalacetophenone, β-phenylacrylophenone, ɣ-oxo-α,ɣ-diphenyl-α-propylene and α-phenyl-β-benzoylethylene.
Chalcones and their derivatives demonstrate wide range of biological activities such as anti-diabetic, anti-neoplastic, anti-hypertensive, anti-retroviral, anti-inflammatory, anti-parasitic, anti-histaminic, anti-malarial, anti-oxidant, anti-fungal, anti-obesity, anti-platelet, anti-tubercular, immunosuppressant, anti-arrhythmic, hypnotic, anti-gout, anxiolytic, anti-spasmodic, anti-nociceptive, hypolipidemic, anti-filarial, anti-angiogenic, anti-protozoal, anti-bacterial, anti-steroidal, cardioprotective, etc.[2] [3] [4] [5]
Chemical properties
Chalcones have two absorption maxima at 280 nm and 340 nm.[6]
Chemical reactions
Synthesis
Chalcones can be prepared by an aldol condensation between benzaldehyde and acetophenone in the presence of sodium hydroxide as a catalyst.
This reaction has been found to work without any solvent at all - a solid-state reaction.[7] The reaction between substituted benzaldehydes and acetophenones can be used as an example of green chemistry in undergraduate education.[8] In a study investigating green syntheses, chalcones were synthesized from the same starting materials in high-temperature water (200 to 350 °C).[9]
Substituted chalcones were also synthesised by piperidine-mediated condensation to avoid side reactions such as multiple condensations, polymerizations, and rearrangements.[10]
Other reactions
An example is the conjugate reduction of the enone by tributyltin hydride:[11]
1-2-3-1: Oxidation Reaction of Chalcones Chalcones can undergo Algar-Flynn oxidation with alkaline hydrogen peroxide to produce flavonols[36] (47), and Additionally I2/DMSO can be used as oxidation reagent to synthesize flavones[37] (48).
The epoxidation of chalcone by hydrogen peroxide occurs very quickly with a high yield of 1-butyl-3-methyl imidazolium tetrafluoroborate ([bmim] BF4) [38] (3)
1-2-3-2: Subtitution reaction of Chalcones
O-Alkylation occurs with the heating reaction of 4-hydroxy chalcones and Alkyle Halides in dry acetone in the presence of anhydrous potasium carbonate.[38] (7)
1-2-3-3: Reduction of chalcones
Reduction reactions of chalcones via hydrogenation are occurred with a catalyst such as; sodium formate or Na2CO3/isopropanol serving as the hydrogen source(61). Another catalyst Pd/C (10%) is also used for the hydrogenation of chalcones (62).
the reduction may occure not only with ethylenic bond in enone part(I) of the compound but the reduction of both carbonyl group and ehtylenic bond(II) may reached with hydrogenation reactions.
1-2-3-4: Addition reaction of chalcones
may under go many different addition reactions with using different chemicals and various conditions.
Chalcones can under go Michael addition reaction usually under basic conditions. Microwave is used for the addition of compounds having active methylene to the chalcones in the presence of potasium carbonate and water.( (52))
Bromination of chalcones can be made with pure starting substance, special reagents and microwave applications (2450 MHz). The usage of microwave (MW) experiments without solvent make them feasible for synthesis of bromo organic compounds. Tetrabutylamonium tribromür (TBATB) is used as bromination reagent to avoid from damages of using molecular bromine. (54)
Diels Alder adduction is occurred between chalcones and cyclopentadiene with the polimerization that is composed by inversing ring opening. Most of chalcones give the endo and exo adduct products with high yield by the reaction of cyclopentadiene with furfurylideneacetone and N,N-diethylaminobenzylidene- (4-hydroxy) acetophenone. Chalcone reactions can be made in both of room temperature and microwawe conditions.(42)
1-2-3-4: Cyclization reaction of chalcones
One of the important class of reactions which chalcones undergo are the ring closure reactions with hydrazine, guanidine, malonitrile etc. affording heterocyclic derivatives such as pyrazoline, pyrimidine, iso-oxazole, cyanopyridine etc.[3,4] The enone functionality present in the chalcones provides an attractive site for 1,3-dinucleophiles affording such heterocyclic ring-systems.[5] article review
See also
References
- ↑ Merck Index, 11th Edition, 2028.
- ↑ Mahapatra, Debarshi Kar; Asati, Vivek; Bharti, Sanjay Kumar (2015-03-06). "Chalcones and their therapeutic targets for the management of diabetes: Structural and pharmacological perspectives". European Journal of Medicinal Chemistry 92: 839–865. doi:10.1016/j.ejmech.2015.01.051.
- ↑ Mahapatra, Debarshi Kar; Bharti, Sanjay Kumar; Asati, Vivek (2015-06-15). "Anti-cancer chalcones: Structural and molecular target perspectives". European Journal of Medicinal Chemistry 98: 69–114. doi:10.1016/j.ejmech.2015.05.004.
- ↑ Mahapatra, Debarshi Kar; Bharti, Sanjay Kumar; Asati, Vivek (2015-08-28). "Chalcone scaffolds as anti-infective agents: Structural and molecular target perspectives". European Journal of Medicinal Chemistry 101: 496–524. doi:10.1016/j.ejmech.2015.06.052.
- ↑ Mahapatra, Debarshi Kar; Bharti, Sanjay Kumar (2016-03-01). "Therapeutic potential of chalcones as cardiovascular agents". Life Sciences 148: 154–172. doi:10.1016/j.lfs.2016.02.048.
- ↑ Photochemistry of chalcone and the application of chalcone-derivatives in photo-alignment layer of liquid crystal display. Dong-mee Song, Kyoung-hoon Jung, Ji-hye Moon and Dong-myung Shin, Optical Materials, 2002, volume 21, pages 667–671, doi:10.1016/S0925-3467(02)00220-3
- ↑ Toda, F., et al., J. Chem. Soc. Perkin Trans. I, 1990, 3207.
- ↑ Palleros, D. R., J. Chem. Educ., 81, 1345 (2004).
- ↑ Comisar, C. M. and Savage, P. E. Green Chem., 6 (2004), 227 - 231. doi:10.1039/b314622g
- ↑ P Venkatesan and S Sumathi, "Piperidine Mediated Synthesis of N-Heterocyclic Chalcones and Their Antibacterial Activity", J. Heterocyclic Chem., 47, 81 (2010).
- ↑ Leusink, A.J.; Noltes, J.G. (1966). "Reaction of organotin hydrides with α,β-unsaturated ketones". Tetrahedron Letters 7 (20): 2221. doi:10.1016/S0040-4039(00)72405-1.