2204-33-3

Usage

Uses

Used in Organic Synthesis:
(2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE is used as a starting material in the synthesis of various pharmaceuticals and functional materials due to its unique molecular structure and reactivity.
Used in Pharmaceutical Industry:
(2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE is used as a precursor for the development of new drugs, leveraging its potential biological activities such as antimicrobial, anticancer, and anti-inflammatory properties.
Used in Antimicrobial Applications:
In the field of antimicrobials, (2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE is utilized for its ability to combat microbial infections, providing a potential alternative to conventional antibiotics.
Used in Anti-inflammatory Applications:
(2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE is employed as an anti-inflammatory agent, potentially reducing inflammation and associated symptoms in various conditions.
Used in Anticancer Applications:
In oncology, (2E,4E)-1-(4-CHLOROPHENYL)-5-PHENYLPENTA-2,4-DIEN-1-ONE is used for its potential to inhibit cancer cell growth and proliferation, offering a novel approach to cancer treatment.

InChI:InChI=1/C17H13ClO/c18-16-12-10-15(11-13-16)17(19)9-5-4-8-14-6-2-1-3-7-14/h1-13H

Upstream product

• 99-91-2 para-chloroacetophenone 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 300-57-2 allylbenzene 
• 676486-15-0 1-(4-chlorophenyl)-2-(dimethyl(oxo)-λ⁶-sulfanylidene)ethan-1-one 
• 108-86-1 bromobenzene 

Downstream Products

• 1234704-12-1 (R,E)-1-(4-chlorophenyl)-3-(nitromethyl)-5-phenylpent-4-en-1-one 
• 1239279-02-7 (S,E)-2-[1-(4-chlorophenyl)-1-oxo-5-phenylpent-4-en-3-yl]malononitrile 
• 1253389-67-1 3-(4'-chlorophenyl)-5-styrylisoxazoline 
• 1315595-96-0 C₂₅H₂₀ClNO 
• 35173-74-1 3,3'-bis-indolyl(phenyl)methane 
• 1415681-06-9 methyl 4'-chloro-3-phenethyl-[1,1'-biphenyl]-4-carboxylate 
• 54006-60-9 5-(4-chloro-phenyl)-1-phenyl-3-styryl-4,5-dihydro-1H-pyrazole 

Relevant academic research and scientific papers

Some 1,3,5-trisubstituted pyrazoline derivatives targeting breast cancer: Design, synthesis, cytotoxic activity, EGFR inhibition and molecular docking

Different 1,3,5-trisubstituted pyrazoline derivatives 2a-c, 3-c, 4a-f, 6a-c, 7a-f and 8a-d were prepared via condensation reaction of the appropriate chalcone 1a-c or 5a-c with various hydrazine derivatives. All compounds were screened for their cytotoxicity against breast MCF-7 cancer cell line and the normal fibroblasts WI-38. Thirteen compounds 2a, 3a, 3c, 4a-d, 6c, 7d, 7e, 8b, 8d and 8f revealed promising cytotoxicity against MCF-7 compared to the reference standard staurosporine and they were safe to the normal fibroblasts WI-38. In addition, compounds 3c, 6c, 7d, 8b and 8d elicited higher cytotoxicity than erlotinib and exhibited promising EGFR inhibitory activity at submicromolar level comparable to that of erlotinib except for compound 8b that may exert its cytotoxicity via another mechanism besides EGFR inhibition. Molecular docking of 3c, 6c, 7d, 8b and 8d in the active site of EGFR confirmed the obtained results.

Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones

The first examples of palladium-catalyzed allylic C-H oxidative allylation of sulfoxonium ylides to afford the corresponding conjugated dienones with moderate to good yields have been established. The features of this novel conversion include mild reaction conditions, wide substrate scope, and excellent regioselectivity.

Antibacterial & antitubercular activities of cinnamylideneacetophenones

Cinnamaldehyde is a natural product with broad spectrum of antibacterial activity. In this work, it was used as a template for design and synthesis of a series of 17 cinnamylideneacetophenones. Phenolic compounds 3 and 4 exhibited MIC (minimum inhibitory

Highly regioselective introduction of aryl substituents via asymmetric 1,4-addition of boronic acids to linear α,β,γ,δ-unsaturated ketones

An efficient palladium(II)-catalyzed regioselective asymmetric 1,4-conjugate addition of arylboronic acids to linear α,β,γ,δ-unsaturated ketones is developed using phosphapalladacycle catalysts. The relevant 1,4-products were obtained exclusively with per

Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids

In our ongoing search for new anti-invasive chemotypes, we have made an excursion from previously reported potent 1,3-diarylpropenones (chalcones) to congeners bearing longer linkers between the aromatic moieties. Nine 1,ω-diarylalkenones, including curcumin and bisdemethoxycurcumin, were evaluated in the chick heart invasion assay. Unfortunately, these compounds proved less potent and more toxic than earlier evaluated chemotypes. In the 1,3-diarylpenta-2,4-dien-1-one series, fluoro and/or trimethoxy substitution caused an increase in potency. This agrees with observations made earlier for the chalcone class.

Synthesis, antimicrobial and cytotoxic activity of novel 1,5 benzodiazepine derivatives

In the present study, a series of novel 2-(substituted phenyl)-3-styryl-2,3-dihydro- 1H-benzo [b] [1,4] diazepines (1-12) has been synthesized from 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones (1a-12a). 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones were prepared by condensing cinnamaldehyde with various aromatic ketones in the presence of 20% NaOH as base. Different 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones on cyclisation with o-phenylene diamine in the presence of NaOH as base resulted in 2-(substituted phenyl)-3-styryl-2,3-dihydro-1H-benzo [b] [1,4] diazepine derivatives. The structures of the newly synthesized compounds were characterized by elemental analysis, IR, 1H NMR and mass spectroscopic studies. All titled compounds were screened for their antimicrobial and cytotoxic activities. Most of the compounds showed promising cytotoxic, antibacterial and antifungal activities.

One-pot synthesis of cinnamylideneacetophenones and their in vitro cytotoxicity in breast cancer cells

A series of cinnamylideneacetophenones were synthesized via a modified Claisen-Schmidt condensation reaction and evaluated for cytotoxicity against breast cancer cells using the Alamar Blue assay. Derivatives 17 and 18 bearing a 2-nitro group on the B rin

Synthesis, characterization and biological activity studies of some substituted pyrimidine derivatives

A new series of substituted 1-phenyl-3-styryl-4,5-dihydo-1H-pyrazoles (TP1-TP9) has been synthesized by the cyclisation of chalcones with phenyl hydrazine and glacial acetic acid and substituted 4-styryl-pyrimidin-2-ols (LP1-LP9) have been synthesized by the condensation of chalcones with urea in the presence of 40% NaOH as a base. The intermediate substituted 1,5-diphenylpenta-2,4-dien-1-ones were synthesized by condensing cinnamaldehyde with various substituted aromatic ketones in presence of 20% NaOH. The title compounds obtained were characterized by IR, 1H NMR, mass spectral data and were screened for antimicrobial, anticancer and antitubercular activity.

Tetra-n-butylammonium bromide: A simple but efficient organocatalyst for alcohol oxidation under mild conditions

A simple but efficient organocatalytic system with 5 mol% tetra-n-butylammonium bromide (TBAB) as the catalyst has been identified for alcohol oxidation for the first time. This organocatalytic system is compatible with a broad range of benzylic/allylic alcohols with various catalytically reactive groups. Besides, it shows excellent selectivity for secondary benzylic alcohols over aliphatic alcohols, and good selectivity over the primary benzylic alcohol site in 4-(1-hydroxyethyl)benzyl alcohol. Thus, the features of simplicity, high efficiency, selectivity and mildness of reaction conditions associated with this TBAB organocatalytic system suggest its potential for widespread use in synthetic chemistry.

Copper-catalyzed asymmetric 1,4-conjugate addition of Grignard reagents to linear α,β,γ,δ-unsaturated ketones

A highly regioselective and enantioselective copper-catalyzed 1,4-conjugate addition of Grignard reagents to linear α,β,γ,δ- unsaturated ketones was developed. The 1,4-addition products were obtained regioselectively in high yields with up to 98% ee. The Royal Society of Chemistry 2013.