22252-16-0

Usage

Uses

Used in Pharmaceutical Research:
(E)-β-(4-Chlorophenyl)acrylophenone is used as a key compound in pharmaceutical research for its potent inhibitory effects on human cytochrome P450 3A4. This makes it a valuable tool in the development of new drugs targeting this enzyme, which is involved in the metabolism of various medications and steroids.
Used in Cancer Treatment:
In the field of oncology, (E)-β-(4-Chlorophenyl)acrylophenone is utilized as a potential therapeutic agent for cancer treatment. Its ability to inhibit specific enzymes can make it a candidate for further research into its anticancer properties.
Used in Inflammation Treatment:
(E)-β-(4-Chlorophenyl)acrylophenone is also being studied for its potential application in treating inflammation. Its inhibitory effects on certain enzymes could contribute to the development of anti-inflammatory drugs.
Used in Organic Synthesis:
(E)-β-(4-Chlorophenyl)acrylophenone serves as a fundamental building block in organic synthesis, allowing for the creation of a variety of complex molecules with diverse applications.
Used in Drug Production:
(E)-β-(4-Chlorophenyl)acrylophenone is employed in the production of various drugs and pharmaceutical products, highlighting its versatility and importance in the pharmaceutical industry.
Safety Note:
It is crucial to handle (E)-β-(4-Chlorophenyl)acrylophenone with care, as it may pose health and environmental risks. Proper safety measures should be taken during its use and disposal to minimize any potential hazards.

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 98-86-2 acetophenone 
• 24721-26-4 (2Z)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one 
• 70-11-1 α-bromoacetophenone 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 38895-95-3 p-chlorochalcone dibromide 
• 153491-51-1 3-(4-Chloro-phenyl)-2,2,2-trimethoxy-5-phenyl-2,3-dihydro-2λ⁵-[1,2]oxaphosphole 
• 133961-78-1 [1-(4-Chloro-phenyl)-3-oxo-3-phenyl-propylsulfanyl]-acetic acid 
• 536-74-3 phenylacetylene 
• 83624-73-1 3-Benzoyl-2,6-bis-(4-chloro-phenyl)-1-cyano-4-hydroxy-4-phenyl-cyclohexanecarboxylic acid ethyl ester 
• 956-04-7 3-(4-chlorophenyl)-1-phenylprop-2-en-1-one 
• 2648-61-5 2,2-dichloroacetophenone 
• 166823-92-3 (2E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-ol 
• 35086-79-4 cinnamoyl chloride 

Downstream Products

• 89451-24-1 4-(4-Chloro-phenyl)-6-hydroxy-6-phenyl-2-thioxo-piperidine-3-carbonitrile; compound with piperidine 
• 74007-56-0 2-(4-Chloro-phenyl)-3,3-dimethoxy-1-phenyl-propan-1-one 
• 101855-02-1 3-(4-chloro-phenyl)-3-methoxyamino-1-phenyl-propan-1-one 
• 78807-79-1 2-[3-(4-Chloro-phenyl)-5-phenyl-4,5-dihydro-pyrazol-1-yl]-1-phenothiazin-10-yl-ethanone 
• 89451-37-6 (3R,4S)-4-(4-Chloro-phenyl)-6-phenyl-2-thioxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile 
• 89451-37-6 (3S,4S)-4-(4-Chloro-phenyl)-6-phenyl-2-thioxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile 
• 23309-52-6 (1R,6S)-6-(4-Chloro-phenyl)-2-oxo-4-phenyl-cyclohex-3-enecarboxylic acid ethyl ester 
• 144309-77-3 (4S,5R)-5-Benzoyl-1-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester 
• 144765-45-7 (1R*,2R*,3S*,4S*,6S*)-(+/-)-2,6-Bis-(4-chlorophenyl)-3-benzoyl-1-(4-bromophenyl)-4-hydroxy-4-phenylcyclohexanecarbonitrile 
• 129226-60-4 3-(4-Chloro-phenyl)-4-(5-methyl-4-nitro-2-phenyl-2H-pyrazol-3-yl)-1-phenyl-butan-1-one 
• 138982-96-4 3-(4-chlorophenyl)-1-phenyl-1-pentanone 
• 143968-99-4 4-(4-Chloro-phenyl)-6-phenyl-pyridin-2-ol 
• 95855-32-6 2-(4-chlorophenyl)-4-oxo-4-phenylbutanenitrile 
• 137594-15-1 4-(4-Chloro-phenyl)-6-phenyl-3-aza-tricyclo[8.4.1.0^2,7]pentadeca-1⁽¹⁴⁾,2⁽⁷⁾,3,8,10,12-hexaene 

Relevant academic research and scientific papers

A four-component Biginelli reaction: new opportunities for the synthesis of functionalized pyrimidines

[Figure not available: see fulltext.] Methyl 5-aroyl-6-aryl-4-methoxy-2-oxo(thioxo)hexahydropyrimidine-4-carboxylates were synthesized by four-component Biginelli reaction of methyl aroylpyruvate, aromatic aldehyde, urea (thiourea), and MeOH in the presence of NaHSO4. The products were obtained in moderate to high yields.

A facile deamination of aziridines using N2O4 under very mild conditions

Various aziridines reacted with N2O4 (2 eq) in the presence of Et3N (1 or 2 eq) in dry THF to give the corresponding ethylenes in good to excellent yields at (-23 °C or -43 °C) in 10 min under Ar.

A NOVEL ROUTE FOR THE SYNTHESIS OF α,β-UNSATURATED ESTERS, KETONES AND NITRILES USING DIBUTYL TELLURIDE

In the presence of dibutyl telluride, α-halo-ester, nitrile, and ketone were found to condense easily with aromatic aldehydes to afford α,β-unsaturated esters, nitriles and ketones in high yields as one-pot reaction.A possible reaction mechanism was proposed.

Synthesis, characterization and antichagasic evaluation of thiosemicarbazones prepared from chalcones and dibenzalacetones

Chagas disease is a neglected disease, being one of the leading causes of death from infectious diseases. In view of the severity of this pathology, this work describes the synthesis of new thiosemicarbazones derived from chalcones and dibenzalacetones as potential drugs for the treatment of this disease. The structures of all compounds were elucidated by infrared (IR) and nuclear magnetic resonance (1H and 13C NMR) spectroscopies. The chalcone derived thiosemicarbazones 10-14 were tested against the intracellular amastigote form of the protozoan Trypanosoma cruzi and had their cytotoxicity assessed using LLC-MK2 cells. The compound 10 (IC50 = 12.25 μM) presented the best activity when compared with the standard drug benznidazole (IC50 = 5.64 μM).

A new method for the synthesis of chalcone derivatives promoted by PPh3/I2under non-alkaline conditions

A straightforward and general method has been developed for the synthesis of chalcone derivatives by a Claisen-Schmidt reaction in the presence of PPh3/I2 in 1,4-dioxane under reflux temperatures. With the condensation of the aromatic ketone and aldehyde occurring at non-strongly alkaline conditions, our proposed method significantly expands the range of applicable substrates, especially for groups that are unstable under alkaline conditions.

Synthesis, characterization and biological evaluation of new 3,5-disubstituted-pyrazoline derivatives as potential anti-Mycobacterium tuberculosis H37Ra compounds

A total of fourteen pyrazoline derivatives were synthesized through cyclo-condensation reactions by chalcone derivatives with different types of semicarbazide. These compounds were characterized by IR, 1D-NMR (1H, 13C and Distortionless Enhancement by Polarization Transfer-DEPT-135) and 2D-NMR (COSY, HSQC and HMBC) as well as mass spectroscopy analysis (HRMS). The synthesized compounds were tested for their antituberculosis activity against Mycobacterium tuberculosis H37Ra in vitro. Based on this activity, compound 4a showed the most potent inhibitory activity, with a minimum inhibitory concentration (MIC) value of 17 μM. In addition, six other synthesized compounds, 5a and 5c–5g, exhibited moderate activity, with MIC ranges between 60 μM to 140 μM. Compound 4a showed good bactericidal activity with a minimum bactericidal concentration (MBC) value of 34 μM against Mycobacterium tuberculosis H37Ra. Molecular docking studies for compound 4a on alpha-sterol demethylase was done to understand and explore ligand– receptor interactions, and to hypothesize potential refinements for the compound.

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.

Heteroleptic copper(I) complexes as energy transfer photocatalysts for the intermolecular [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides

The [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides can be effectively catalyzed by heteroleptic copper(I) complexes. The reactions were carried out under mild reaction conditions and the products were obtained in 20–72% yield under visible light irradiation. The copper-based photocatalyst comprised of the rigid phenanthroline ligand with substituents at the 2,9-positions and the 4,7-positions showed high activity in the photodimerization via an energy transfer pathway.

New promising levofloxacin derivatives: Design, synthesis, cytotoxic activity screening, Topo2β polymerase inhibition assay, cell cycle apoptosis profile analysis

Newly designed levofloxacin analogues were synthesized to act as topoisomerase II beta inhibitors (Topo2β). Their cytotoxic activity was screened against breast, liver, and leukemia cancer cell lines. The best activity against liver cancer cell line (Hep3B) was exhibited by the target compounds 3c, 3e, 4a, and 6d (IC50 = 2.33, 1.38, 0.60 and 0.43, respectively). (L-SR) leukemia cancer cell line was pronouncedly affected by compounds 3b, 3g and 4a (IC50 = 1.62, 1.41 and 1.61, sequentially). 3c possessed the best activity against breast cancer cell line (MCF-7) with IC50 = 0.66. Compounds 3c, 3e, 3g, 4a and 4c exhibited Topo2β inhibition activities exceeding etoposide and levofloxacin as reference drugs and variant cell lines. In DNA-Flow cytometry cell cycle analysis, compound 3c arrested the cell cycle at G2/M phase like etoposide and levofloxacin, while compounds 3e and 4a exhibit its arrest at S phase. In addition, 3c, 3e and 4a showed a significant elevation in active caspase-3 levels (10.01, 8.98 and 10.71 folds, respectively). The effect of the new compounds on normal cells was also investigated including breast (MCF10a), liver (THLE2), and lymphocytic (PCS-800-011) normal cell lines.

Modular access to 1,2-allenyl ketones based on a photoredox-catalysed radical-polar crossover process

Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developedviathe reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and allenation, the mechanism based on a photoredox-neutral-catalysed radical-polar crossover process has been proposed. Synthetic applications of allenes have also been demonstrated.