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'''Chalcone''' is the [[organic compound]] C<sub>6</sub>H<sub>5</sub>C(O)CH=CHC<sub>6</sub>H<sub>5</sub>. It is an [[Alpha-beta Unsaturated carbonyl compounds|α,β-unsaturated ketone]]. A variety of important biological compounds are known collectively as chalcones or [[chalconoid]]s.<ref>{{cite journal |doi=10.1002/(SICI)1097-0010(20000515)80:7<1073::AID-JSFA568>3.0.CO;2-B|title=Flavanones, Chalcones and Dihydrochalcones - Nature, Occurrence and Dietary Burden|year=2000|last1=Tomás-Barberán|first1=Francisco A.|last2=Clifford|first2=Michael N.|journal=Journal of the Science of Food and Agriculture|volume=80|issue=7|pages=1073–1080}}</ref> |
'''Chalcone''' is the [[organic compound]] C<sub>6</sub>H<sub>5</sub>C(O)CH=CHC<sub>6</sub>H<sub>5</sub>. It is an [[Alpha-beta Unsaturated carbonyl compounds|α,β-unsaturated ketone]]. A variety of important biological compounds are known collectively as chalcones or [[chalconoid]]s.<ref>{{cite journal |doi=10.1002/(SICI)1097-0010(20000515)80:7<1073::AID-JSFA568>3.0.CO;2-B|title=Flavanones, Chalcones and Dihydrochalcones - Nature, Occurrence and Dietary Burden|year=2000|last1=Tomás-Barberán|first1=Francisco A.|last2=Clifford|first2=Michael N.|journal=Journal of the Science of Food and Agriculture|volume=80|issue=7|pages=1073–1080}}</ref> As bioactive substances, fluorescent materials, and chemical intermediates, they are widely known. Chalcones have been used in medicinal chemistry as antioxidants, anticancer agents, diabetes medications, antiviral agents, antimalarial agents, and more. Aside from being utilized as medicines, they may also be employed as liquid crystals, fluorescent scaffolds, metal sensors, corrosion inhibitors, and plant growth promoters.<ref>{{Cite journal |last=Nayak |first=Yogeesha N. |last2=Gaonkar |first2=Santosh L. |last3=Sabu |first3=Mariya |date=2023-01-04 |title=Chalcones: Versatile intermediates in heterocyclic synthesis |url=https://onlinelibrary.wiley.com/doi/10.1002/jhet.4617 |journal=Journal of Heterocyclic Chemistry |language=en |pages=jhet.4617 |doi=10.1002/jhet.4617 |issn=0022-152X}}</ref> |
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== Chemical properties == |
== Chemical properties == |
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==Potential pharmacology== |
==Potential pharmacology== |
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Chalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation.<ref name=pmid28914193>{{cite journal |doi=10.2174/1568026617666170914160446 |pmid=28914193 |title=Chalcone Derivatives: Anti-inflammatory Potential and Molecular Targets Perspectives |journal=Current Topics in Medicinal Chemistry |volume=17 |issue=28 |pages=3146–3169 |year=2017 |last1=Mahapatra |first1=Debarshi Kar |last2=Bharti |first2=Sanjay Kumar |last3=Asati |first3=Vivek }}</ref> Some 2′-amino chalcones have been studied as potential antitumor agents.<ref name="XiaYang2000">{{cite journal|last1=Xia|first1=Yi|last2=Yang|first2=Zheng-Yu|last3=Xia|first3=Peng|last4=Bastow|first4=Kenneth F.|last5=Nakanishi|first5=Yuka|last6=Lee|first6=Kuo-Hsiung|title=Antitumor agents. Part 202: Novel 2′-amino chalcones: design, synthesis and biological evaluation|journal=Bioorganic & Medicinal Chemistry Letters|volume=10|issue=8|year=2000|pages=699–701|issn=0960-894X|doi=10.1016/S0960-894X(00)00072-X|pmid=10782667}}</ref><ref name="SantosPinhanelli2017">{{cite journal|last1=Santos|first1=Mariana B.|last2=Pinhanelli|first2=Vitor C.|last3=Garcia|first3=Mayara A.R.|last4=Silva|first4=Gabriel|last5=Baek|first5=Seung J.|last6=França|first6=Suzelei C.|last7=Fachin|first7=Ana L.|last8=Marins|first8=Mozart|last9=Regasini|first9=Luis O.|title=Antiproliferative and pro-apoptotic activities of 2′- and 4′-aminochalcones against tumor canine cells|journal=European Journal of Medicinal Chemistry|volume=138|year=2017|pages=884–889|issn=0223-5234|doi=10.1016/j.ejmech.2017.06.049|pmid=28738308|url=https://repositorio.unesp.br/bitstream/11449/174929/1/2-s2.0-85024884865.pdf|hdl=11449/174929|hdl-access=free}}</ref> Chalcones are of interest in [[medicinal chemistry]] and have been described as a [[privileged scaffold]].<ref name="zhuang_2017">{{cite journal |last1=Zhuang |first1=Chunlin |last2=Zhang |first2=Wen |last3=Sheng |first3=Chunquan |last4=Zhang |first4=Wannian |last5=Xing |first5=Chengguo |last6=Miao |first6=Zhenyuan |title=Chalcone: A Privileged Structure in Medicinal Chemistry |journal=Chemical Reviews |date=28 June 2017 |volume=117 |issue=12 |pages=7762–7810 |doi=10.1021/acs.chemrev.7b00020|pmid=28488435 |pmc=6131713 }}</ref> |
Chalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation.<ref name=pmid28914193>{{cite journal |doi=10.2174/1568026617666170914160446 |pmid=28914193 |title=Chalcone Derivatives: Anti-inflammatory Potential and Molecular Targets Perspectives |journal=Current Topics in Medicinal Chemistry |volume=17 |issue=28 |pages=3146–3169 |year=2017 |last1=Mahapatra |first1=Debarshi Kar |last2=Bharti |first2=Sanjay Kumar |last3=Asati |first3=Vivek }}</ref> Some 2′-amino chalcones have been studied as potential antitumor agents.<ref name="XiaYang2000">{{cite journal|last1=Xia|first1=Yi|last2=Yang|first2=Zheng-Yu|last3=Xia|first3=Peng|last4=Bastow|first4=Kenneth F.|last5=Nakanishi|first5=Yuka|last6=Lee|first6=Kuo-Hsiung|title=Antitumor agents. Part 202: Novel 2′-amino chalcones: design, synthesis and biological evaluation|journal=Bioorganic & Medicinal Chemistry Letters|volume=10|issue=8|year=2000|pages=699–701|issn=0960-894X|doi=10.1016/S0960-894X(00)00072-X|pmid=10782667}}</ref><ref name="SantosPinhanelli2017">{{cite journal|last1=Santos|first1=Mariana B.|last2=Pinhanelli|first2=Vitor C.|last3=Garcia|first3=Mayara A.R.|last4=Silva|first4=Gabriel|last5=Baek|first5=Seung J.|last6=França|first6=Suzelei C.|last7=Fachin|first7=Ana L.|last8=Marins|first8=Mozart|last9=Regasini|first9=Luis O.|title=Antiproliferative and pro-apoptotic activities of 2′- and 4′-aminochalcones against tumor canine cells|journal=European Journal of Medicinal Chemistry|volume=138|year=2017|pages=884–889|issn=0223-5234|doi=10.1016/j.ejmech.2017.06.049|pmid=28738308|url=https://repositorio.unesp.br/bitstream/11449/174929/1/2-s2.0-85024884865.pdf|hdl=11449/174929|hdl-access=free}}</ref> Chalcones are of interest in [[medicinal chemistry]] and have been described as a [[privileged scaffold]].<ref name="zhuang_2017">{{cite journal |last1=Zhuang |first1=Chunlin |last2=Zhang |first2=Wen |last3=Sheng |first3=Chunquan |last4=Zhang |first4=Wannian |last5=Xing |first5=Chengguo |last6=Miao |first6=Zhenyuan |title=Chalcone: A Privileged Structure in Medicinal Chemistry |journal=Chemical Reviews |date=28 June 2017 |volume=117 |issue=12 |pages=7762–7810 |doi=10.1021/acs.chemrev.7b00020|pmid=28488435 |pmc=6131713 }}</ref> |
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== Organic chemistry == |
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chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of pyrazoles, aurones etc.<ref>{{Cite journal |last=Nayak |first=Yogeesha N. |last2=Gaonkar |first2=Santosh L. |last3=Sabu |first3=Mariya |date=2023-01-04 |title=Chalcones: Versatile intermediates in heterocyclic synthesis |url=https://onlinelibrary.wiley.com/doi/10.1002/jhet.4617 |journal=Journal of Heterocyclic Chemistry |language=en |pages=jhet.4617 |doi=10.1002/jhet.4617 |issn=0022-152X}}</ref> |
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==See also== |
==See also== |
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Revision as of 06:08, 18 January 2023
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| Names | |
|---|---|
| Preferred IUPAC name
Chalcone[2] | |
| Systematic IUPAC name
(2E)-1,3-Diphenylprop-2-en-1-one | |
| Other names
Chalkone
Benzylideneacetophenone Phenyl styryl ketone benzalacetophenone β-phenylacrylophenone γ-oxo-α,γ-diphenyl-α-propylene α-phenyl-β-benzoylethylene. | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.002.119 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C15H12O | |
| Molar mass | 208.260 g·mol−1 |
| Appearance | pale yellow solid |
| 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) |
| -125.7·10−6 cm3/mol | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Chalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids.[3] As bioactive substances, fluorescent materials, and chemical intermediates, they are widely known. Chalcones have been used in medicinal chemistry as antioxidants, anticancer agents, diabetes medications, antiviral agents, antimalarial agents, and more. Aside from being utilized as medicines, they may also be employed as liquid crystals, fluorescent scaffolds, metal sensors, corrosion inhibitors, and plant growth promoters.[4]
Chemical properties
Chalcones have two absorption maxima at 280 nm and 340 nm.[5]
Synthesis
Chalcone is usually prepared by an aldol condensation between benzaldehyde and acetophenone.[6]
This reaction, which can be carried out without any solvent, is so reliable that it is used in as an example of green chemistry in undergraduate education.[7]
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.[8]
Potential pharmacology
Chalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation.[9] Some 2′-amino chalcones have been studied as potential antitumor agents.[10][11] Chalcones are of interest in medicinal chemistry and have been described as a privileged scaffold.[8]
Organic chemistry
chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of pyrazoles, aurones etc.[12]
See also
References
- ^ Merck Index, 11th Edition, 2028
- ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 722. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
- ^ Tomás-Barberán, Francisco A.; Clifford, Michael N. (2000). "Flavanones, Chalcones and Dihydrochalcones - Nature, Occurrence and Dietary Burden". Journal of the Science of Food and Agriculture. 80 (7): 1073–1080. doi:10.1002/(SICI)1097-0010(20000515)80:7<1073::AID-JSFA568>3.0.CO;2-B.
- ^ Nayak, Yogeesha N.; Gaonkar, Santosh L.; Sabu, Mariya (2023-01-04). "Chalcones: Versatile intermediates in heterocyclic synthesis". Journal of Heterocyclic Chemistry: jhet.4617. doi:10.1002/jhet.4617. ISSN 0022-152X.
- ^ Song, Dong-mee; Jung, Kyoung-Hoon; Moon, Ji-hye; Shin, Dong-Myung (2003). "Photochemistry of chalcone and the application of chalcone-derivatives in photo-alignment layer of liquid crystal display". Optical Materials. 21 (1–3): 667–71. Bibcode:2003OptMa..21..667S. doi:10.1016/S0925-3467(02)00220-3.
- ^ E. P. Kohler, H. M. Chadwell (1922). "Benzalacetophenone". Organic Syntheses. 2: 1. doi:10.15227/orgsyn.002.0001.
- ^ Palleros, Daniel R (2004). "Solvent-Free Synthesis of Chalcones". Journal of Chemical Education. 81 (9): 1345. Bibcode:2004JChEd..81.1345P. doi:10.1021/ed081p1345.
- ^ a b Zhuang, Chunlin; Zhang, Wen; Sheng, Chunquan; Zhang, Wannian; Xing, Chengguo; Miao, Zhenyuan (28 June 2017). "Chalcone: A Privileged Structure in Medicinal Chemistry". Chemical Reviews. 117 (12): 7762–7810. doi:10.1021/acs.chemrev.7b00020. PMC 6131713. PMID 28488435.
- ^ Mahapatra, Debarshi Kar; Bharti, Sanjay Kumar; Asati, Vivek (2017). "Chalcone Derivatives: Anti-inflammatory Potential and Molecular Targets Perspectives". Current Topics in Medicinal Chemistry. 17 (28): 3146–3169. doi:10.2174/1568026617666170914160446. PMID 28914193.
- ^ Xia, Yi; Yang, Zheng-Yu; Xia, Peng; Bastow, Kenneth F.; Nakanishi, Yuka; Lee, Kuo-Hsiung (2000). "Antitumor agents. Part 202: Novel 2′-amino chalcones: design, synthesis and biological evaluation". Bioorganic & Medicinal Chemistry Letters. 10 (8): 699–701. doi:10.1016/S0960-894X(00)00072-X. ISSN 0960-894X. PMID 10782667.
- ^ Santos, Mariana B.; Pinhanelli, Vitor C.; Garcia, Mayara A.R.; Silva, Gabriel; Baek, Seung J.; França, Suzelei C.; Fachin, Ana L.; Marins, Mozart; Regasini, Luis O. (2017). "Antiproliferative and pro-apoptotic activities of 2′- and 4′-aminochalcones against tumor canine cells" (PDF). European Journal of Medicinal Chemistry. 138: 884–889. doi:10.1016/j.ejmech.2017.06.049. hdl:11449/174929. ISSN 0223-5234. PMID 28738308.
- ^ Nayak, Yogeesha N.; Gaonkar, Santosh L.; Sabu, Mariya (2023-01-04). "Chalcones: Versatile intermediates in heterocyclic synthesis". Journal of Heterocyclic Chemistry: jhet.4617. doi:10.1002/jhet.4617. ISSN 0022-152X.
External links
- Chalcone on reference.md Archived 2020-09-25 at the Wayback Machine