94-41-7 Usage
Description
Chalcone, with the chemical formula C6H5C(O)CH=CHC6H5, is an α,β-unsaturated ketone that belongs to a group of important biological compounds known as chalcones or chalconoids. These compounds exhibit a range of biological activities, including antibacterial, antifungal, antitumor, and anti-inflammatory properties. Chalcones also play a crucial role as intermediates in the biosynthesis of flavonoids, which are widespread in plants and possess an array of biological activities. Additionally, chalcones are involved in the Auwers synthesis of flavones.
Uses
Used in Pharmaceutical Industry:
Chalcone is used as a key intermediate in the synthesis of pharmacologically-interesting heterocyclic systems, such as pyrazolines and pyrimidines. These heterocyclic systems have potential applications in the development of new drugs with various therapeutic effects.
Used in Cancer Treatment:
Chalcone has demonstrated its potential as an antitumor agent, particularly in inhibiting the proliferation of human breast cancer cell lines, MCF-7 and MDA-MB-231. It achieves this by inducing apoptosis and blocking cell cycle progression in the G2/M phase, which can contribute to the development of novel cancer treatments.
Preparation
Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones.Chalcones can be prepared by an aldol condensation between a benzaldehyde and an 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. The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education.In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 °C).
Biological Activity
1,3-Diphenyl-2-propenone (chalcone) inhibits the proliferation of human breast cancer cell lines, MCF-7 and MDA-MB-231 by inducing apoptosis and blocking cell cycle progression in the G2/M phase. It is an inhibitor of Plasmodium falciparum cyclin-dependent protein kinases.
Biochem/physiol Actions
1,3-Diphenyl-2-propenone (chalcone) inhibits the proliferation of human breast cancer cell lines, MCF-7 and MDA-MB-231 by inducing apoptosis and blocking cell cycle progression in the G2/M phase. It is an inhibitor of Plasmodium falciparum cyclin-dependent protein kinases.
Safety Profile
Poison by intravenous
route. See also KETONES. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Purification Methods
Crystallise it from EtOH by warming to 50o (about 5mL/g), iso-octane, or toluene/pet ether, or recrystallise it from MeOH, and then twice from hexane. SKIN IRRITANT. [Beilstein 7 IV 1658.]
Check Digit Verification of cas no
The CAS Registry Mumber 94-41-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 4 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 94-41:
(4*9)+(3*4)+(2*4)+(1*1)=57
57 % 10 = 7
So 94-41-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H/b12-11-
94-41-7Relevant articles and documents
Silver-Catalyzed Intramolecular C-2 Selective Acylation of Indoles with Aldehydes: An Atom-Economical Entry to Indole-Indolone Scaffolds
Wang, Xiaoxia,Li, Zhongfeng,Cao, Shengli,Rao, Honghua
, p. 2059 - 2065 (2016)
A direct annulation reaction of N-(2-formylaryl)indoles has been developed, which can provide a new entry to biologically and medicinally important indole-indolone scaffolds via a silver-catalyzed direct oxidative coupling between aldehyde C H and sp2C H bonds for the first time. Remarkably, this strategy displayed excellent functional group compatibilities, thereby suggesting its wide potential for applications in developing and synthesizing new drug-like compounds containing indole-indolone frameworks. (Figure presented.) .
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Egger,Schloegl
, p. 398,404 (1964)
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Arnould,J.C.,Pete,J.P.
, p. 2459 - 2462 (1975)
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The kinetics and mechanism of reactions of cis- and trans-chalcones with amines.
Menger,Smith
, p. 4211 - 4216 (1969)
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Lutz,Jordan
, p. 40,90 (1950)
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Boron-catalyzed dehydrative allylation of 1,3-diketones and β-ketone esters with 1,3-diarylallyl alcohols in water
Zhang, Guo-Min,Zhang, Hua,Wang, Bei,Wang, Ji-Yu
, p. 17025 - 17031 (2021/05/25)
A metal-free catalytic allylation with atom economy and green environment friendly was developed. Allylic alcohols could be directly dehydrated in water by B(C6F5)3, without using any base additives. The reaction can afford the corresponding monoallylated product in moderate to high yield and has been performed on a gram-scale, and a quaternary carbon center can be constructed for the active methine compounds of 1,3-diketones or β-ketone esters in this process. The product can be further converted, such as the synthesis of tetra-substituted pyrazole compounds, or 1,4-dienes and functionalized dihydropyrans.
Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide
Matsumoto, Shoji,Marumoto, Hayato,Akazome, Motohiro,Otani, Yasuhiko,Kaiho, Tatsuo
, p. 590 - 599 (2021/03/29)
The selective reduction of ?,￠-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ￠ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ￠-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.
