THC Science

Chalcone^[1]
Names
	Preferred IUPAC name Chalcone
	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
CAS Number	94-41-7; 614-47-1 ((E)-Chalcone) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27618 ;
ChemSpider	6921 ;
ECHA InfoCard	100.002.119
PubChem CID	637760;
UNII	5S5A2Q39HX ;
CompTox Dashboard (EPA)	DTXSID20873536 ;
	InChI InChI=1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H Key: DQFBYFPFKXHELB-UHFFFAOYSA-N ; InChI=1/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H Key: DQFBYFPFKXHELB-UHFFFAOYAP;
	SMILES O=C(C=Cc1ccccc1)c2ccccc2;
Properties
Chemical formula	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)
Magnetic susceptibility (χ)	-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). verify (what is ?) Infobox references

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:

Uses in organic chemistry[edit]

Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of pyrazoles and aurones.^[12]

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

[1] Merck Index, 11th Edition, 2028

[iupac2013-2] "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.

[3] 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.

[4] 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.

[zhuang_2017-5] 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.

[6] E. P. Kohler, H. M. Chadwell (1922). "Benzalacetophenone". Organic Syntheses. 2: 1. doi:10.15227/orgsyn.002.0001.

[7] Palleros, Daniel R (2004). "Solvent-Free Synthesis of Chalcones". Journal of Chemical Education. 81 (9): 1345. Bibcode:2004JChEd..81.1345P. doi:10.1021/ed081p1345.

[pmid28914193-8] 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.

[XiaYang2000-9] 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.

[SantosPinhanelli2017-10] 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.

[11] 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.

[12] 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.

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@@ Line 1: / Line 1: @@
 {{for|the butterflies|Chalcone (skipper)}}
-{{cleanup|reason=Convert long prose list(s) to bulleted list(s).|date=March 2021}}
 {{chembox
 | Verifiedfields = changed
@@ Line 12: / Line 12: @@
 | ImageSize1 = 220
 | ImageAlt1 = Ball-and-stick model of the chalcone molecule
+| ImageFile2 =
 | 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>
 | SystematicName = (2''E'')-1,3-Diphenylprop-2-en-1-one
-| 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.
 |Section1={{Chembox Identifiers
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
@@ Line 24: / Line 25: @@
 | StdInChIKey = DQFBYFPFKXHELB-UHFFFAOYSA-N
 | CASNo = 94-41-7
-| CASNo_Ref = {{cascite|correct|CAS}}
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 5S5A2Q39HX
-| CASNo2_Ref = {{cascite|changed|??}}
 | CASNo2 = 614-47-1
+| CASNo2_Ref = {{cascite|correct|CAS}}
 | CASNo2_Comment = ((''E'')-Chalcone)
 | PubChem = 637760
@@ Line 37: / Line 39: @@
 |Section2={{Chembox Properties
 | C=15 | H=12 | O=1
-| Appearance =
+| Appearance = pale yellow solid
 | Density =1.071 g/cm<sup>3</sup>
 | MeltingPtC = 55 to 57
@@ Line 46: / Line 48: @@
  }}
 }}
-'''Chalcone''' is an [[aromatic]] [[ketone]] and an [[Alpha-beta Unsaturated carbonyl compounds|enone]] that forms the central core for a variety of important biological compounds, which are known collectively as chalcones or [[chalconoid]]s. Alternative names for chalcone include benzylideneacetophenone, phenyl styryl ketone, benzalacetophenone, ''β''-phenylacrylophenone, ''γ''-oxo-''α'',''γ''-diphenyl-''α''-propylene, and ''α''-phenyl-''β''-benzoylethylene.
+'''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.
 == Chemical properties ==
-Chalcones have two absorption maximums at 280&nbsp;nm and 340&nbsp;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>
+Chalcones have two absorption maxima at 280&nbsp;nm and 340&nbsp;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>
+==Biosynthesis==
-== Chemical reactions ==
+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 />
-=== Synthesis ===
-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>
+==Laboratory synthesis ==
+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>
 :[[Image:Chalcone preparation.svg|400px|preparation of chalcone]]
-This reaction can be carried out without any solvent as a [[Solid-state physics|solid-state]] reaction.<ref>{{cite journal |doi=10.1039/P19900003207 |title=Aldol condensations in the absence of solvent: Acceleration of the reaction and enhancement of the stereoselectivity |journal=Journal of the Chemical Society, Perkin Transactions 1 |issue=11 |pages=3207–9 |year=1990 |last1=Toda |first1=Fumio |last2=Tanaka |first2=Koichi |last3=Hamai |first3=Koki }}</ref>  The reaction between substituted benzaldehydes and acetophenones can be used 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> In a study investigating green syntheses, chalcones were synthesized from the same starting materials in high-temperature water (200 to 350&nbsp;°C).<ref>{{cite journal |doi=10.1039/b314622g |title=Kinetics of crossed aldol condensations in high-temperature water |journal=Green Chemistry |volume=6 |issue=4 |pages=227–31 |year=2004 |last1=Comisar |first1=Craig M |last2=Savage |first2=Phillip E }}</ref>
+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>
+==Potential pharmacology==
-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>
+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>
+==Uses==
-=== Other reactions ===
+===Medicinal uses===
-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>
+In [[medicinal chemistry]], chalcones have been used as:
+*[[antioxidant]]s
+*[[Anticancer agent]]s
+*[[antidiabetic drug]]s
+*[[antiviral drug]]s
+*[[antimalarial drug]]s and more.
+===Industrial uses===
-:[[File:Conjugate reduction chalcone.svg|500px|Conjugate reduction of chalcone]]
+In chemical industries, they are employed as:
+*[[liquid crystal]]s
+*[[fluorescent]] [[scaffold (chemistry)|chemical scaffold]]s
+*[[metal sensor]]s
+*[[corrosion inhibitor]]s
+*[[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>
+===Uses in organic chemistry===
-,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>
+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>
-:[[File:Lasri condensation reaction.jpg|700px]]
-==Biosynthesis==
-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 />
-==Potential pharmacology==
-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}}</ref>
 ==See also==
@@ Line 83: / Line 92: @@
 ==External links==
-* [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 }}
 [[Category:Chalconoids]]

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Latest revision as of 23:03, 27 June 2023