94-41-7 Usage
Description
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.They show antibacterial, antifungal, antitumor and anti-inflammatory properties. They are also intermediates in the biosynthesis of flavonoids, which are substances widespread in plants and with an array of biological activities. Chalcones are also intermediates in the Auwers synthesis of flavones.
Chemical Properties
light yellow powder
Uses
Different sources of media describe the Uses of 94-41-7 differently. You can refer to the following data:
1. 1,3-Diphenyl-2-propenone was used in the preparation of pharmacologically-interesting heterocyclic systems like pyrazolines and pyrimidines.
2. Chalcone is used in the preparation of pharmacologically-interesting heterocyclic systems like pyrazolines and pyrimidines. It also 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.
Definition
ChEBI: A member of the class of chalcones that is acetophenone in which one of the methyl hydrogens has been replaced by a benzylidene group.
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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Sequential Catalytic Functionalization of Aryltriazenyl Aldehydes for the Synthesis of Complex Benzenes
Seo, Sangwon,Gao, Ming,Paffenholz, Eva,Willis, Michael C.
, p. 6091 - 6098 (2021/05/29)
We demonstrate that aryltriazenes can promote three distinctive types of C-H functionalization reactions, allowing the preparation of complex benzene molecules with diverse substitution patterns. 2-Triazenylbenzaldehydes are shown to be efficient substrates for Rh(I)-catalyzed intermolecular alkyne hydroacylation reactions. The resulting triazene-substituted ketone products can then undergo either a Rh(III)-catalyzed C-H activation, or an electrophilic aromatic substitution reaction, achieving multifunctionalization of the benzene core. Subsequent triazene derivatization provides traceless products.
One-pot two-step reaction of selenosulfonate with isocyanides and allyl alcohol under aqueous conditions: Atom-economic synthesis of selenocarbamates and allyl sulfones
Ai, Jing-Jing,Li, Jian,Ji, Shun-Jun,Wang, Shun-Yi
supporting information, p. 721 - 724 (2020/07/24)
In many reactions involving selenosulfonate or thiosulfonate, the sulfone group often leaves in form of benzenesulfinic acid or sodium benzenesulfinate. A one-pot two-step reaction of selenosulfonate with isocyanides and allyl alcohol under aqueous conditions to afford selenocarbamates and allyl sulfone compounds is reported. The sulfinic acid as the first-step side product is converted to the allyl sulfone compound by water promoted reaction with allyl alcohol. Water acts as both an oxygen source of selenocarbamates and as a promoter to drive the second step reaction. The reactions have the advantages of mild conditions, green, environment-friendly, and high atomic economy.
