94-41-7

Usage

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.]

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-

Upstream product

• 6263-84-9 1,3,5-triphenyl-1,5-pentanedione 
• 4360-47-8 cinnamonitrile 
• 742-43-8 1,3-diphenyl-3-(N-phenylamino)propanone 
• 24825-07-8 δ-truxin diketone 
• 7149-37-3 4-benzoyl-1,3,5,7-tetraphenylheptane-1,7-dione 
• 5350-97-0 1,3-diphenyl-3-piperidin-1-yl-propan-1-one 
• 861378-94-1 (2-bromo-3-oxo-1,3-diphenyl-propyl)-phenyl-phosphinic acid 
• 74864-02-1 dimethyl-2,2 diphenyl-3,5 oxo-5 pentanal 
• 108-24-7 acetic anhydride 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 64-19-7 acetic acid 
• 917-64-6 methyl magnesium iodide 
• 124-41-4 sodium methylate 

Downstream Products

• 52236-60-9 10-(3-oxo-1,3-diphenyl-propyl)-anthrone 
• 5350-97-0 1,3-diphenyl-3-piperidin-1-yl-propan-1-one 
• 55860-91-8 (2E)-1,1,2,4-tetraphenyl-1,3-butadiene 
• 4529-77-5 (3-oxo-1,3-diphenyl-propyl)-phenyl-phosphinic acid 
• 861552-93-4 5-hydroxy-2,3,5-triphenyl-valeric acid 
• 6265-29-8 3-ethoxycarbonyl-4,6-diphenyl-2,6-hexanedione 
• 6287-66-7 ethyl 2-oxo-4,6-diphenylcyclohex-3-enecarboxylate 
• 53852-96-3 2-(1,3-Diphenyl-3-oxopropyl)cyclohexane-1,3-dione 
• 6323-01-9 5-oxo-2-(3-oxo-1,3-diphenyl-propyl)-2,3,5-triphenyl-valeronitrile 
• 62071-27-6 3-benzoyl-1,2-diphenylpropanecarbonitrile 
• 5339-82-2 2-(4-nitro-phenyl)-5-oxo-3,5-diphenyl-valeronitrile 
• 117402-91-2 ethyl-2-benzoyl-3,5-diphenyl-5-oxopentanoate 
• 854450-84-3 (2,2-diethoxy-4-phenyl-cyclobutyl)-phenyl ketone 
• 37904-94-2 1,3-diphenyl-3-(4-methylphenylamino)propan-1-one 

Relevant academic research and scientific papers

Silver-Catalyzed Intramolecular C-2 Selective Acylation of Indoles with Aldehydes: An Atom-Economical Entry to Indole-Indolone Scaffolds

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.) .

Copper(II)-Promoted Oxidation/[3+2]Cycloaddition/Aromatization Cascade: Efficient Synthesis of Tetrasubstituted NH -Pyrrole from Chalcones and Iminodiacetates

A simple and highly efficient method for the preparation of tetrasubstituted NH -pyrrole from a wide range of chalcones and diethyl iminodiacetates via a Cu(OAc) 2 -promoted oxidation/[3+2]cycloaddition/aromatization cascade reaction has been developed. This reaction proceeds through dehydrogenations, deamination, and oxidative cyclization, affording the corresponding products in good to excellent yields. This convenient methodology for constructing tetrasubstituted NH -pyrroles has several advantages over existing methods, such as the use of easily accessible chalcones and readily available diethyl iminodiacetates, and mild reaction conditions. A wide range of substrates are tolerated.

Application of basic isoreticular nanoporous metal-organic framework: IRMOF-3 as a suitable and efficient catalyst for the synthesis of chalcone

A highly porous isoreticular metal-organic framework (IRMOF-3) was synthesized and employed as a novel efficient heterogeneous catalyst for the synthesis of chalcone via Claisen-Schmidt condensation. The effects of temperature, catalyst amount and solvent

Ranks of Carbon Leaving Groups in Alkene-forming Elimination

Carbon leaving groups in alkene-forming eliminations are exceptionally poor and their ranks show no correlation with the pKa of the conjugate carbon acid; the extent of bond cleavage in the transition state is evidently critical in determining rank.

Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite

Earth abundant metals are much less expensive, promising, valuable metals and could be served as catalysts for the borrowing hydrogen reaction, dehydrogenation and heterocycles synthesis, instead of noble metals. The uniformly dispersed zinc composites were designed, synthesized and carefully characterized by means of XPS, EDS, TEM and XRD. The resulting zinc composite showed good catalytic activity for the N-alkylation of amines with amines, ketones with alcohols in water under base-free conditions, while unsaturated carbonyl compounds could also be synthesized by tuning the reaction conditions. Importantly, it was the first time to realize the synthesis of 2-aryl-1H-benzo[d]imidazole derivatives by using this zinc composite under green conditions. Meanwhile, this zinc catalyst could be easily recovered and reused for at least five times.

Boron-catalyzed dehydrative allylation of 1,3-diketones and β-ketone esters with 1,3-diarylallyl alcohols in water

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.

Catalyst- and acid-free Markovnikov hydration of alkynes in a sustainable H2O/ethyl lactate system

An efficient and sustainable protocol for the hydration of alkynes has been developed under metal/acid/catalyst/ligand-free conditions in a water/ethyl lactate mixture. The hydrogen-bond network in the ethyl lactate and water mixture plays a crucial and decisive role in activating the alkynes for hydration to afford the corresponding methyl ketones. This strategy gives the Markovnikov (ketone) addition product selectively over other possible products. The essential role of hydrogen bonding has been confirmed by experimental and theoretical techniques. A probable mechanism has been suggested by various control tests. The efficacy of the method has been further explored for the competent production of value-added α,β-unsaturated carbonyl compounds through the reaction of aldehydes with alkynes as ketonic surrogates. The environmentally benign hydration method takes place under mild conditions, has broad functional-group compatibility, and uses the ethyl lactate/water (1:3) medium as a “green alternative” in the absence of any hazardous, harmful, or expensive substances.

One-pot two-step reaction of selenosulfonate with isocyanides and allyl alcohol under aqueous conditions: Atom-economic synthesis of selenocarbamates and allyl sulfones

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.

Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide

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.

Method for preparing phenyl propenone compound by catalyzing phenylacetylene through molecular sieve

The invention belongs to the field of molecular sieve catalysis and organic synthesis, and discloses a method for preparing a phenyl propenone compound by catalyzing phenylacetylene through a molecular sieve, which comprises the following steps: adding a phenylacetylene compound I, aldehyde II and a molecular sieve catalyst into a small reaction kettle without adding an organic solvent and any other assistants; performing stirring to react for 0.25-6 hours under the condition of heating at 30-90 DEG C, cooling the reaction kettle to room temperature, performing diluting with ethyl acetate, andcentrifugally separating the catalyst to obtain the phenyl allyl ketone compound III. The molecular sieve catalyst provided by the invention is H-beta of which the silica-alumina ratios are respectively 14 and 29. The method is simple in reaction process, high in catalytic activity and selectivity, recyclable, environmentally friendly and capable of achieving large-scale industrial production.