2373-95-7

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Pentadien-1-one, 1-(4-methoxyphenyl)-5-phenylis used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of complex molecular structures that can exhibit therapeutic effects.
Used in Perfumery:
In the perfume industry, 2,4-Pentadien-1-one, 1-(4-methoxyphenyl)-5-phenylis used as a fragrance ingredient, capitalizing on its distinct odor to create unique scents for various perfumes.
Used in Organic Synthesis:
2,4-Pentadien-1-one, 1-(4-methoxyphenyl)-5-phenylis utilized as a reactant in organic synthesis, playing a crucial role in the formation of complex molecules that can be used in a wide range of applications across different industries.
Used in Research and Development:
2,4-Pentadien-1-one, 1-(4-methoxyphenyl)-5-phenylis also used in research settings to study its potential biological activities, such as its antimicrobial and antioxidant properties, which could lead to new applications in medicine and other fields.

Upstream product

• 104-55-2 3-phenyl-propenal 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 14371-10-9 (E)-3-phenylpropenal 
• 19115-30-1 1-(4-methoxyphenyl)-2-propyn-1-ol 
• 123-11-5 4-methoxy-benzaldehyde 
• 16469-68-4 1-(4-methoxyphenyl)-2-propyn-1-one 
• 201852-49-5 potassium (E)-trifluoro(styryl)borate 

Downstream Products

• 61022-41-1 1-(4-methoxyphenyl)-5-phenylpentan-1-one 
• 3185-61-3 1-Phenyl-5-(4-methoxy-phenyl)-pentadien-(1,3)-ol-⁽⁵⁾ 
• 78722-47-1 [Rh(η4-PhCH=CHCH=CH(O)C6H4-p-OMe)2Cl] 
• 1234704-11-0 (R,E)-1-(4-methoxyphenyl)-3-(nitromethyl)-5-phenylpent-4-en-1-one 
• 1239279-01-6 (S,E)-2-[1-(4-methoxyphenyl)-1-oxo-5-phenylpent-4-en-3-yl]malononitrile 
• 1315595-93-7 C₂₆H₂₃NO₂ 
• 35173-74-1 3,3'-bis-indolyl(phenyl)methane 
• 102316-72-3 (E)-1-(3-(4-methoxyphenyl)-5-styryl-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one 

Relevant academic research and scientific papers

Synthesis of 2,6-diaryl-1,2-dihydropyridines through a 6π-electrocyclization of N-sulfonylazatrienes

The development of an efficient synthetic method toward substituted 1,2-dihydropyridines from cinnamylideneacetophenones is reported. The key intermediates N-sulfonylazatrienes were synthesized through a TiCl4-mediated direct condensation of primary sulfonamides with the substituted (E,E)-cinnamylideneacetophenones. The 6π-electrocyclization of these intermediates, catalyzed by a Lewis acid, selectively afforded the desired products in good yields.

Crystal structure, Hirshfeld, computational biomolecular investigations, and MTT assay studies of amino pyrimidine derivative as EGFR kinase domain inhibitor

A nitrogen heterocyclic pyrimidine fused heterocyclic derivative 4-(4-Methoxyphenyl)-6-(2-phenylethyl)pyrimidin-2-amine (MPPPA), was synthesized and crystal structure is identified by single crystal XRD method. The asymmetric structure of MPPPA belongs to orthorhombic (Pna21) space group with unit cell parameters a = 14.6720(7) ?, b = 14.3922(6) ?, c = 7.6334(3) ?, α=β=γ= 90° and Z = 4. Two inter-molecular N3-H3A···N1i, N3-H3B···N2ii hydrogen bonds that fomrs R22(8) ring motifs in zigzag format that run along c-axis is noticed in supramolecular network of MPPPA crystal structure. The optimized structure of the compound is investigated using density functional theory (DFT). Energies of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) with other global reactivity parameters are computed. Further, surface map of molecular electrostatic potential (MEP) is determined using the electron density of the compound to recognize the reactivity region of our compound. To understand the supramolecular features, the close contacts of the molecular crystal of the complex is evaluated using Hirshfeld surface analysis by CrystalExplorer 17.5 program. Enrichment ratio is calculated to find the propensity of the intermolecular contacts in building the crystal packing. Bioactivity score, drug-likeness and ADMET properties of the compound is analysed to determine its potential bioactivity. In-silico molecular docking was performed to examine the EGFR inhibition of the MPPPA compound as a potential anticancer agent by docking with Crystal structure of EGFR kinase domain protein (PDB ID: 2J6M) using PyRx program. The MPPPA ligand is docked with 2J6M protein by three conventional N-H…O type hydrogen bonds, one C-H…O hydrogen bond, and various hydrophobic bonds with docking energy = -9.8 kcal/mol. Further, anticancer activity of MPPPA was investigated against lung cancer (A549), cervical cancer (HeLa) and liver cancer (Hep3b) cell lines and compared with activity of standard drug Gefitinib. In vitro results showed higher cytotoxicity of MPPPA with A549 cells and could be treated as lead molecule for lung cancer drug design.

Palladium-Catalyzed Aminomethylation of Nitrodienes and Dienones via Double C—N Bond Activation

A new strategy for the generation of the active Pd-alkyl species from aminal via C—N bond activation has been established, in which the formation of zwitterionic intermediate through aza-Michael addition of aminal to nitrodienes or dienones is identified as a key step for the activation of the C—N bond. The efficient strategy has enabled a new palladium-catalyzed α-aminomethylation of nitrodienes and dienones via double C—N bond activation. The scope and versatility of the reaction were demonstrated and a broad range of substrates bearing electron-donating and -withdrawing groups on the aromatic rings were all compatible with this reaction to furnish the desired α-aminomethylated products in moderate to good yields with excellent regioselectivities and E/Z selectivities.

Curcumin-cinnamaldehyde hybrids as antiproliferative agents against women’s cancer cells

Curcumin and cinnamaldehyde are natural products whose antineoplastic activity has been well explored in biological evaluations. However, their poor chemical stability under physiological conditions has been an obstacle to their use as therapeutic agents. Herein, we designed and synthesized two series of curcumin-cinnamaldehyde hybrids by removing reactive functionalities, including β-diketone and aldoxyl moieties. All compounds were evaluated by the MTT assay to determine their antiproliferative activity against women’s cancer cells. Compound 5a (3′-hydroxychalcone) demonstrated potent antiproliferative activity against all cancer cell lines tested, with IC50 values ranging from 2.7 to 36.5 μM. Compound 5a was more active and selective than curcumin and cinnamaldehyde (parent compounds) against the CaSki, SiHa, C33, and A431 cell lines, displaying a higher selectivity index (SI = 8.5) than curcumin (SI = 0.8) toward the non-tumorigenic HaCaT cell line. Clonogenic experiments indicated that compound 5a inhibited A431 colony formation in a concentration-dependent manner. In addition, 5a was more stable than its parent compounds in pH 7.4 at 37 °C. In silico investigations suggested that 5a has good drug-likeness properties. In conclusion, our results indicate the use of curcumin and cinnamaldehyde as parent compounds for the design of hybrids with attractive antiproliferative activity and chemical stability.

Relay Catalysis to Synthesize β-Substituted Enones: Organocatalytic Substitution of Vinylogous Esters and Amides with Organoboronates

Organocatalysis was shown to facilitate conjugate additions to vinylogous esters and amides for the first time. Subsequent elimination of a β-alcohol or amine provided π-conjugated β-substituted enones. Remarkably, nucleophile addition to the electron-rich vinylogous substrates is more rapid than classical enones, forming monosubstituted products. A doubly organocatalytic (organic diol and methyl aniline) conjugate addition synthesized the products directly from alkynyl ketones. Both of these catalytic transformations are orthogonal to transition metal catalysis, allowing for good yields, easily accessible or commercially available reagents, high selectivity, reagent recovery and recyclability, facile scalability, and exceptional functional group tolerance.

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.

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

Design, synthesis and bioactivity of chalcones and its analogues

The Vernohia anthelmintica L.'s extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and α, β-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a–15a, 20a and 1b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40?μg/mL.

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.