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 
• 6935-75-7 2-bromo-1,3-diphenyl-2-propen-1-one 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 742-43-8 1,3-diphenyl-3-(N-phenylamino)propanone 
• 19805-05-1 ε-truxilldiketone 
• 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 
• 859951-06-7 3-hydroxy-2-methyl-3,5-diphenyl-pent-4-enoic acid ethyl ester 
• 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 
• 861534-70-5 5-oxo-2,2,3,5-tetraphenyl-valeric acid 

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.

Iridium and copper supported on silicon dioxide as chemoselective catalysts for dehydrogenation and borrowing hydrogen reactions

High active ligand usually plays an important role during catalysis and synthesis chemistry. A new and efficient benzotriazole-pyridinyl-silane ligand (BPS) was designed, and the corresponding iridium and copper catalysts were synthesized and thoroughly characterized by means of EDS, TEM, and XPS. The resulting iridium composite revealed excellent catalytic activity for the reaction of tert-butanesulfinamide with benzyl alcohols, while copper catalyst could realize the synthesis of unsaturated carbonyl compounds through the reaction of benzyl alcohols with ketones. This provided an efficient method for selective synthesis of unsaturated carbonyl compounds from benzyl alcohols and ketones in high yields with good recovery performance.

Iridium Complexes as Efficient Catalysts for Construction of α-Substituted Ketones via Hydrogen Borrowing of Alcohols in Water

Ketones are of great importance in synthesis, biology, and pharmaceuticals. This paper reports an iridium complexes-catalyzed cross-coupling of alcohols via hydrogen borrowing, affording a series of α-alkylated ketones in high yield (86 %–95 %) and chemoselectivities (>99 : 1). This methodology has the advantages of low catalyst loading (0.1 mol%) and environmentally benign water as the solvent. Studies have shown the amount of base has a great impact on chemoselectivities. Meanwhile, deuteration experiments show water plays an important role in accelerating the reduction of the unsaturated ketones intermediates. Remarkably, a gram-scale experiment demonstrates this methodology of iridium-catalyzed cross-coupling of alcohols has potential application in the practical synthesis of α-alkylated ketones.

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.

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.