Opabinia regalis (talk | contribs) →Biological Target Inhibition Perspectives: rm section, WP:NOT for raw screening hits |
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{{for|the butterflies|Chalcone (skipper)}} |
{{for|the butterflies|Chalcone (skipper)}} |
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| ImageSize1 = 220 |
| ImageSize1 = 220 |
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| ImageAlt1 = Ball-and-stick model of the chalcone molecule |
| ImageAlt1 = Ball-and-stick model of the chalcone molecule |
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| ImageFile2 = |
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| PIN = Chalcone<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 722 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> |
| PIN = Chalcone<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 722 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> |
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| SystematicName = (2''E'')-1,3-Diphenylprop-2-en-1-one |
| SystematicName = (2''E'')-1,3-Diphenylprop-2-en-1-one |
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| OtherNames = Chalkone<br />Benzylideneacetophenone<br />Phenyl styryl ketone |
| OtherNames = Chalkone<br />Benzylideneacetophenone<br />Phenyl styryl ketone<br />benzalacetophenone<br /> ''β''-phenylacrylophenone<br />''γ''-oxo-''α'',''γ''-diphenyl-''α''-propylene<br /> ''α''-phenyl-''β''-benzoylethylene. |
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|Section1={{Chembox Identifiers |
|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| StdInChIKey = DQFBYFPFKXHELB-UHFFFAOYSA-N |
| StdInChIKey = DQFBYFPFKXHELB-UHFFFAOYSA-N |
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| CASNo = 94-41-7 |
| CASNo = 94-41-7 |
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| |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 5S5A2Q39HX |
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⚫ | |||
| CASNo2 = 614-47-1 |
| CASNo2 = 614-47-1 |
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⚫ | |||
| CASNo2_Comment = ((''E'')-Chalcone) |
| CASNo2_Comment = ((''E'')-Chalcone) |
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| PubChem = 637760 |
| PubChem = 637760 |
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|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
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| C=15 | H=12 | O=1 |
| C=15 | H=12 | O=1 |
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| Appearance = |
| Appearance = pale yellow solid |
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| Density =1.071 g/cm<sup>3</sup> |
| Density =1.071 g/cm<sup>3</sup> |
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| MeltingPtC = 55 to 57 |
| MeltingPtC = 55 to 57 |
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'''Chalcone''' is |
'''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> They are widely known bioactive substances, fluorescent materials, and chemical intermediates. |
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== Chemical properties == |
== Chemical properties == |
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Chalcones have two absorption |
Chalcones have two absorption maxima at 280 nm and 340 nm.<ref>{{cite journal |doi=10.1016/S0925-3467(02)00220-3 |title=Photochemistry of chalcone and the application of chalcone-derivatives in photo-alignment layer of liquid crystal display |journal=Optical Materials |volume=21 |issue=1–3 |pages=667–71 |year=2003 |last1=Song |first1=Dong-mee |last2=Jung |first2=Kyoung-Hoon |last3=Moon |first3=Ji-hye |last4=Shin |first4=Dong-Myung |bibcode=2003OptMa..21..667S}}</ref> |
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==Biosynthesis== |
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== Chemical reactions == |
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Chalcones and [[chalconoids]] are synthesized in plants as [[secondary metabolite]]s. 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 plant|vascular]]) and several "lower" ([[non-vascular plant|non-vascular]]) plants.<ref name=zhuang_2017 /> |
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=== Synthesis === |
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Chalcones can be prepared by an [[aldol condensation]] between [[benzaldehyde]] and [[acetophenone]] in the presence of [[sodium hydroxide]] as a [[catalyst]].<ref>{{Cite journal|last1=Dumitru|first1=Sîrbu|last2=Ion|first2=Marin|date=2011|title=SYNTHESIS AND IR, NMR CARACTERISATION OF NEW P-(N,N-DIPHENYLAMINO) CHALCONES|url=http://www.cjm.asm.md/synthesis-and-ir-nmr-caracterisation-of-new-p-n-n-diphenylamino-chalcones}}</ref><ref>{{Cite journal|last1=Gómez-Rivera|first1=Abraham|last2=Aguilar-Mariscal|first2=Hidemí|last3=Romero-Ceronio|first3=Nancy|last4=Roa-de la Fuente|first4=Luis F.|last5=Lobato-García|first5=Carlos E.|date=2013-10-15|title=Synthesis and anti-inflammatory activity of three nitro chalcones|url=http://www.sciencedirect.com/science/article/pii/S0960894X13010019|journal=Bioorganic & Medicinal Chemistry Letters|language=en|volume=23|issue=20|pages=5519–5522|doi=10.1016/j.bmcl.2013.08.061|pmid=24012185|issn=0960-894X|doi-access=free}}</ref> |
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==Laboratory synthesis == |
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Chalcone is usually prepared by an [[aldol condensation]] between [[benzaldehyde]] and [[acetophenone]].<ref>{{cite journal |doi=10.15227/orgsyn.002.0001|title=Benzalacetophenone|journal=Organic Syntheses|year=1922|volume=2|page=1|author=E. P. Kohler, H. M. Chadwell}}</ref> |
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:[[Image:Chalcone preparation.svg|400px|preparation of chalcone]] |
:[[Image:Chalcone preparation.svg|400px|preparation of chalcone]] |
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This reaction can be carried out without any solvent |
This reaction, which can be carried out without any solvent, is so reliable that it is often given as an example of [[green chemistry]] in undergraduate education.<ref>{{cite journal |doi=10.1021/ed081p1345 |title=Solvent-Free Synthesis of Chalcones |journal=Journal of Chemical Education |volume=81 |issue=9 |pages=1345 |year=2004 |last1=Palleros |first1=Daniel R |bibcode=2004JChEd..81.1345P }}</ref> |
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Substituted chalcones were also synthesised by piperidine-mediated condensation to avoid side reactions such as multiple condensations, polymerizations, and rearrangements.<ref>{{cite journal |doi=10.1002/jhet.268 |title=Piperidine mediated synthesis ofn-heterocyclic chalcones and their antibacterial activity |journal=Journal of Heterocyclic Chemistry |volume=47 |issue=1 |pages=81–84 |year=2009 |last1=Venkatesan |first1=P |last2=Sumathi |first2=S }}</ref> |
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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> |
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==Uses== |
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=== Other reactions === |
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===Medicinal uses=== |
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An example is the [[conjugate reduction]] of the enone by [[tributyltin hydride]]:<ref>{{cite journal |doi=10.1016/S0040-4039(00)72405-1 |title=Reaction of organotin hydrides with α,β-unsaturated ketones |journal=Tetrahedron Letters |volume=7 |issue=20 |pages=2221–5 |year=1966 |last1=Leusink |first1=A.J |last2=Noltes |first2=J.G |hdl=1874/17014 |hdl-access=free }}</ref> |
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In [[medicinal chemistry]], chalcones have been used as: |
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*[[antioxidant]]s |
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*[[Anticancer agent]]s |
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*[[antidiabetic drug]]s |
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*[[antiviral drug]]s |
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*[[antimalarial drug]]s and more. |
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===Industrial uses=== |
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:[[File:Conjugate reduction chalcone.svg|500px|Conjugate reduction of chalcone]] |
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In chemical industries, they are employed as: |
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*[[liquid crystal]]s |
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*[[fluorescent]] [[scaffold (chemistry)|chemical scaffold]]s |
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*[[metal sensor]]s |
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*[[corrosion inhibitor]]s |
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*[[plant hormone]]s.<ref>{{Cite journal |last1=Nayak |first1=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 |s2cid=255212828 |issn=0022-152X}}</ref> |
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===Uses in organic chemistry=== |
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3,5-Disubstituted 1''H''-pyrazoles can be produced from a suitably substituted chalcone by reaction with [[hydrazine hydrate]] in the presence of elemental [[sulfur]]<ref>{{cite journal |doi=10.1002/jhet.5570450231 |title=New one step synthesis of 3,5-disubstituted pyrazoles under microwave irradiation and classical heating |journal=Journal of Heterocyclic Chemistry |volume=45 |issue=2 |pages=503–5 |year=2008 |last1=Outirite |first1=Moha |last2=Lebrini |first2=Mounim |last3=Lagrenée |first3=Michel |last4=Bentiss |first4=Fouad }}</ref> or [[sodium persulfate]],<ref>{{cite journal |doi=10.3987/COM-13-12867 |title=One-Pot Synthesis of 3,5-Diphenyl-1H-pyrazoles from Chalcones and Hydrazine under Mechanochemical Ball Milling |journal=Heterocycles |volume=89 |pages=103–12 |year=2014 |last1=Zhang |first1=Ze |last2=Tan |first2=Ya-Jun |last3=Wang |first3=Chun-Shan |last4=Wu |first4=Hao-Hao }}</ref> or by using a [[hydrazone]] in which case an [[azine]] is produced as a by-product. The specific case for formation of 3,5-diphenyl-1''H''-pyrazole from chalcone itself can be represented as:<ref>{{cite journal|title = Metal-free and FeCl<sub>3</sub>-catalyzed synthesis of azines and 3,5-diphenyl-1''H''-pyrazole from hydrazones and/or ketones monitored by high resolution ESI<sup>+</sup>-MS|year = 2018|journal = Indian Journal of Chemistry, Section B|volume = 57B|issue = 3|pages = 362–373|url = http://nopr.niscair.res.in/handle/123456789/43824|first1 = Jamal|last1 = Lasri|first2 = Ali I.|last2 = Ismail}}</ref> |
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Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of [[pyrazole]]s and [[aurone]]s.<ref>{{Cite journal |last1=Nayak |first1=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 |s2cid=255212828 |issn=0022-152X}}</ref> |
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:[[File:Lasri condensation reaction.jpg|700px]] |
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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> |
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The therapeutic (anti-cancer, anti-bacterial, anti-fungal, anti-viral, anti-ameobic, anti-malarial, anti-tubercular, nematicidal, anti-oxidant, inhibitors against various therapeutic targets, etc.), catalytic, chemosensing, and photosensitizing potentials of various Metal (Iron, Ruthenium, Platinum, Copper, Zinc, Cobalt, Manganese, Nickel, Osmium, Chromium, Tellurium, Boron, Tungsten, and Silicon)-Chalcone complexes have also been reported. <ref>Mahapatra, D. K., Bharti, S. K., Asati, V., & Singh, S. K. (2017). Perspectives of medicinally privileged chalcone based metal coordination compounds for biomedical applications. European journal of medicinal chemistry, 174, 142-158. DOI: https://doi.org/10.1016/j.ejmech.2019.04.032</ref><ref>{{cite journal |last1=Ramesh |first1=Deepthi |last2=Joji |first2=Annu |last3=Vijayakumar |first3=Balaji Gowrivel |last4=Sethumadhavan |first4=Aiswarya |last5=Mani |first5=Maheswaran |last6=Kannan |first6=Tharanikkarasu |title=Indole chalcones: Design, synthesis, in vitro and in silico evaluation against Mycobacterium tuberculosis |journal=European Journal of Medicinal Chemistry |date=15 July 2020 |volume=198 |pages=112358 |doi=10.1016/j.ejmech.2020.112358 |url=https://doi.org/10.1016/j.ejmech.2020.112358 |language=en |issn=0223-5234}}</ref> |
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==See also== |
==See also== |
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==External links== |
==External links== |
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* [http://www.reference.md/files/D047/mD047188.html Chalcone on reference.md] |
* [http://www.reference.md/files/D047/mD047188.html Chalcone on reference.md] {{Webarchive|url=https://web.archive.org/web/20200925011431/http://www.reference.md/files/D047/mD047188.html |date=2020-09-25 }} |
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[[Category:Chalconoids]] |
[[Category:Chalconoids]] |
Latest revision as of 23:03, 27 June 2023
Names | |
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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)
|
|
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.002.119 |
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
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] They are widely known bioactive substances, fluorescent materials, and chemical intermediates.
Chemical properties[edit]
Chalcones have two absorption maxima at 280 nm and 340 nm.[4]
Biosynthesis[edit]
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.[5]
Laboratory synthesis[edit]
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 often given as an example of green chemistry in undergraduate education.[7]
Potential pharmacology[edit]
Chalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation.[8] Some 2′-amino chalcones have been studied as potential antitumor agents.[9][10] Chalcones are of interest in medicinal chemistry and have been described as a privileged scaffold.[5]
Uses[edit]
Medicinal uses[edit]
In medicinal chemistry, chalcones have been used as:
Industrial uses[edit]
In chemical industries, they are employed as:
- liquid crystals
- fluorescent chemical scaffolds
- metal sensors
- corrosion inhibitors
- plant hormones.[11]
Uses in organic chemistry[edit]
Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of pyrazoles and aurones.[12]
See also[edit]
References[edit]
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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. S2CID 255212828.
- ^ 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. S2CID 255212828.
External links[edit]
- Chalcone on reference.md Archived 2020-09-25 at the Wayback Machine