962-10-7

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(4-ethoxyphenyl)-3-phenylprop-2-en-1-one is used as a key intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique chemical structure allows it to be a versatile building block in the creation of a wide range of medicinal compounds.
Used in Organic Chemical Reactions:
As a reagent, 1-(4-ethoxyphenyl)-3-phenylprop-2-en-1-one is employed in organic chemical reactions to facilitate the formation of new compounds. Its participation in these reactions is valuable for the development of novel organic substances with potential applications in various fields.
Used in the Production of Other Compounds:
1-(4-ethoxyphenyl)-3-phenylprop-2-en-1-one serves as a fundamental building block for the production of a variety of other compounds, contributing to the diversification of chemical products available for different industries.
Used in Biological Research:
1-(4-ethoxyphenyl)-3-phenylprop-2-en-1-one is used in biological research as a subject of study for its potential anti-inflammatory and anti-cancer properties. The exploration of these properties could lead to the discovery of new therapeutic approaches for treating inflammation and cancer.

Upstream product

• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 699-08-1 1-ethoxy-4-iodobenzene 
• 140-10-3 (E)-3-phenylacrylic acid 
• 70080-55-6 (4-ethoxy-phenyl)-glyoxylic acid 
• 103-73-1 Phenetole 
• 100-52-7 benzaldehyde 
• 1676-63-7 4'-ethoxyacetophenone 
• 99-93-4 4-Hydroxyacetophenone 

Downstream Products

• 79182-00-6 3-(4-ethoxyphenyl)-5-phenylisoxazole 
• 94910-09-5 3-Morpholino-3-phenyl-1-<4-ethoxy-phenyl>-propan-1-on 

Relevant academic research and scientific papers

Molecular docking of 4-ehoxychalcones on oxidoreductase/pirin inhibitors and cytotoxic evaluation on breast/skin cancer cell lines

Background: The role of α, β unsaturated propenone derivatives, has attracted the chemists for its biological importance. An attempt is made to reveal the interaction between breast and skin cancer cell lines with the help of molecular docking studies. Ob

Design, synthesis, docking studies and monoamine oxidase inhibition of a small library of 1-acetyl- and 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazoles

New N-acetyl/N-thiocarbamoylpyrazoline derivatives were designed and synthesized in high yields to assess their inhibitory activity and selectivity against human monoamine oxidase A and B. The most important chiral compounds were separated into their single enantiomers and tested. The impact of the substituents at N1, C3 and C5 positions as well the influence of the configuration of the C5 on the biological activity were analyzed. Bulky aromatic groups at C5 were not tolerated. p-Prenyloxyaryl moiety at C3 oriented the selectivity toward the B isoform. The results were also corroborated by molecular modelling studies providing new suggestions for the synthesis of privileged structures to serve as lead compounds for the treatment of mood disorders and neurodegenerative diseases.

Synthesis and structure-activity relationships of chalcone derivatives as inhibitors of ovarian cancer cell growth

Background: Ovarian cancer remains a disease with a poor five year survival rate. As such, novel therapies are needed. Natural chalcones as well as their synthetic derivatives have shown biological activity in a number of areas including the inhibition of cancer cell growth. Objective: To synthesize a library of chalcone derivatives, including novel structures, and determiner the inhibition of ovarian cancer cell growth and Structure-activity-relationships. Methods: The Claisen-Schmidt condensation reaction between substituted acetophenones and aromatic aldehydes was used to produce a series of novel chalcones in moderate to excellent yields and good purity. Cellular proliferation of CA-OV3 cells was measured with a MTS assay. Results: Out of the thirty-four synthesized compounds, eight are new derivatives. The synthesized compounds were characterized by 1H NMR, 13C NMR, and HRMS. Biological evaluation of these β-phenylacrylophenone derivatives in CA-OV3 cells showed interesting antiproliferative activities providing initial structure – activity information. Conclusion: Fourteen of the thirty-four tested compounds showed significant activity, with several showing near complete inhibition of growth at 100 μM. The structure-activity relationships suggest that modification to the A ring is widely tolerated and that electron-donating modifications to the B ring are beneficial to activity. Electron-withdrawing modifications to the B ring did not show inhibition of cell growth.

Iron-facilitated oxidative radical decarboxylative cross-coupling between α-oxocarboxylic acids and acrylic acids: An approach to α,β-unsaturated carbonyls

The first Fe-facilitated decarboxylative cross-coupling reaction between α-oxocarboxylic acids and acrylic acids in aqueous solution has been developed. This transformation is characterized by its wide substrate scope and good functional group compatibility utilizing inexpensive and easily accessible reagents, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyls frequently found in bioactive compounds. The synthetic potential of the coupled products is also demonstrated in subsequent functionalization reactions. Preliminary mechanism studies suggest that a free radical pathway is involved in this process: the generation of an acyl radical from α-oxocarboxylic acid via the excision of carbon dioxide followed by the addition of an acyl radical to the α-position of the double bond in acrylic acid then delivers the α,β-unsaturated carbonyl adduct through the extrusion of another carbon dioxide.

A new and direct synthesis of chalcones via TFAA-H3PO 4 mediated c-c bond forming reaction

A number of α,β-unsaturated carboxylic acids were reacted with electron rich arenes or heteroarene in the presence of trifluoroacetic anhydride (TFAA) and H3PO4 at room temperature to give a variety of chalcone derivatives in good to

Ferrocenyl chalcones versus organic chalcones: A comparative study of their nematocidal activity

A series of 30 organic chlacones and 33 ferrocenyl (Fc) chalcones were synthesized and characterized by melting point, elemental analysis, spectroscopy (1H NMR and FTIR) and, in two cases, by X-ray crystallography. The biological activity of each compound (10-4 M in DMSO) against the model nematode Caenorhabditis elegans was examined in terms of % mortality (percent nematodes that died) and % fecundity (percent nematodes that reproduced) and compared to that obtained for the control medium (1% DMSO) over a 14-day period. Detailed conformational analyses for two Fc-chalcones (studied also by X-ray crystallography) were performed via molecular modeling studies. In general, the organic chalcones were found to be less polar than their Fc analogs. Some structure-activity relationships (SARs) were determined: (a) The nematocidal activities of the organic chalcones in this series were found to be much greater than those of their ferrocenyl analogs. (b) The position of the carbonyl group played a central role in the biological activity of both classes of chalcones studied. (c) For both classes of chalcones, lipophilicity of a compound seemed to play a significant role in its nematocidal activity. (d) The planarity of a ferrocenyl-chlacone seems to play a role in its activity.

Development of a general palladium-catalyzed carbonylative heck reaction of aryl halides

The first general palladium-catalyzed carbonylative vinylation of aryl halides with olefins in the presence of CO has been developed. Applying a catalyst system consisting of [(cinnamyl)PdCl]2 and bulky imidazolyl-phosphine ligand L1 allows for the efficient and selective synthesis of α,β-unsaturated ketones under mild reaction conditions. Starting from easily available aryl halides and olefins, versatile building blocks can be prepared in a straightforward manner. The generality and functional group tolerance of this novel protocol is demonstrated.

Shape-persistent binuclear cyclometalated platinum(II) luminophores: Pushing π-mediated excimeric fluid emissions into the NIR region and ion-induced perturbations

The synthesis and spectroscopic properties of new binuclear cyclometalated 6-aryl-2, 2'-bipyridine (C,N,N) platinum(II) complexes tethered by a xanthene backbone has been reported. The rigid bridging unit is chosen to preclude intramolecular metal-metal interactions and hence MMLCT states, while allowing π-stacking interactions within the (Pt-C, N, N) moiety, which has pushed the associated excimeric-type emission into the near-infrared region. The emission features and particularly the relative intensities of the high- and low-energy emissions for desirable electronic and recognition/signaling, are independent of complex concentration. These emissions are susceptible to perturbations in different solvents and by selected metal ions. The NIR emissions are desirable reporting tools for biomolecular probes and chemosensing applications.

Antimalarial alkoxylated and hydroxylated chalones: Structure-activity relationship analysis

Chalcones with 2′,3′,4′-trimethoxy, 2′,4′-dimethoxy, 4′-methoxy, 4′-ethoxy, 2′,4′-dihydroxy, and 4′-hydroxy groups on ring B were synthesized and evaluated in vitro against Plasmodium falciparum (K1) in a [3H] hypoxanthine uptake assay. The other ring A was quinoline, pyridine, naphthalene, or phenyl rings with electron-donating or electron-withdrawing substituents of varying lipophilicities. Trimethoxy 6 and 27, dimethoxy 7, 8, 29, and methoxy 31 analogues had good in vitro activities (IC50 5μM). 3-Quinolinyl ring A derivatives were well represented among the active compounds. Hydroxylated chalcones were less active than the corresponding alkoxylated analogues. When evaluated in vivo, 8 and 208 were comparable to chloroquine in extending the lifespan of infected mice. Multivariate data analysis showed that in vitro activity was mainly determined by the properties of ring B. Quantitative structure - activity relationship models with satisfactory predictive ability were obtained for various B ring chalcones using projections to latent structures. A model with good predictability was proposed for 19 active chalcones. Size and hydrophobicity were identified as critical parameters.

Improved microwave-induced synthesis of chalcones and related enones

Various chalcones and related enones have been synthesised in unsealed vessels in a domestic microwave oven.Considerable increase in the reaction rate has been observed with better yields.