6552-67-6

Usage

Uses

Used in Organic Synthesis:
(E)-1-(4-methoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one is used as a key intermediate for the synthesis of various organic compounds due to its versatile reactivity and structural features.
Used in Medicinal Chemistry:
(E)-1-(4-methoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one is used as a starting material for the development of new pharmaceuticals, leveraging its antioxidant, antimicrobial, and anti-inflammatory properties.
Used in Pharmaceutical Applications:
(E)-1-(4-methoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one is used as a building block for the creation of novel drugs, taking advantage of its biological activities and potential to be modified into more complex molecules with therapeutic benefits.
Used in Antioxidant Applications:
In the field of health and nutrition, (E)-1-(4-methoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one is used as an antioxidant agent to protect cells from oxidative damage, which may contribute to various diseases and aging.
Used in Antimicrobial Applications:
(E)-1-(4-methoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one is used as an antimicrobial agent, potentially useful in the development of new antibiotics or as a preservative in the food and cosmetics industries.
Used in Anti-inflammatory Applications:
In the pharmaceutical and healthcare sectors, (E)-1-(4-methoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one is used as an anti-inflammatory agent to help reduce inflammation and alleviate pain associated with various conditions.

InChI:InChI=1/C16H13NO4/c1-21-15-9-5-13(6-10-15)16(18)11-4-12-2-7-14(8-3-12)17(19)20/h2-11H,1H3/b11-4+

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 27547-03-1 (4-methoxy-phenyl)-[3-(4-nitro-phenyl)-oxiranyl]-methanone 
• 64-19-7 acetic acid 
• 51410-44-7 1-(4-methoxylphenyl)-2-propen-1-ol 
• 24067-17-2 4-nitrophenylboronic acid 
• 636-98-6 p-nitrobenzene iodide 
• 19115-30-1 1-(4-methoxyphenyl)-2-propyn-1-ol 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 30278-80-9 4'-methoxy-4-aminochalcone 
• 77636-34-1 (4-Methoxy-phenyl)-[4-(4-nitro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-methanone 
• 87544-63-6 (4-Methoxy-phenyl)-[4-(4-nitro-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-methanone 
• 75745-34-5 3-(4-Methoxy-phenyl)-5-(4-nitro-phenyl)-4,5-dihydro-pyrazole-1-carbaldehyde 
• 2387-74-8 1-(4-methoxyphenyl)-2-(4-nitrophenyl)ethane-1,2-dione 
• 75745-31-2 3-(4-methoxyphenyl)-5-(4-nitrophenyl)-2-pyrazoline 
• 27547-03-1 (4-Methoxy-phenyl)-[(2S,3R)-3-(4-nitro-phenyl)-oxiranyl]-methanone 
• 19268-77-0 3-(4-methoxy-phenyl)-5-(4-nitro-phenyl)-1-phenyl-4,5-dihydro-1H-pyrazole 
• 75745-33-4 3-(4-Methoxy-phenyl)-5-(4-nitro-phenyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrazole 
• 75745-32-3 1-Benzenesulfonyl-3-(4-methoxy-phenyl)-5-(4-nitro-phenyl)-4,5-dihydro-1H-pyrazole 
• 75745-37-8 1-[3-(4-Methoxy-phenyl)-5-(4-nitro-phenyl)-4,5-dihydro-pyrazol-1-yl]-butan-1-one 
• 68063-58-1 1-p-Methoxyphenyl-3-p-aminophenylpropanol-1 
• 93850-86-3 [(4S,5R)-2,2-Dimethyl-5-(4-nitro-phenyl)-[1,3]dioxolan-4-yl]-(4-methoxy-phenyl)-methanone 
• 1217356-20-1 7-(4-methoxyphenyl)-1,3-dimethyl-5-(4-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Synthesis, characterization and structure–activity relationship of non-linear optical response of chalcone derivatives with in silico insights

Fifteen chalcone derivatives having D–A–D, D–A–A and A–A–D architectures have been synthesized by Claisen–Schmidt condensation reaction and characterized by UV–Vis, IR, 1H-NMR, 13C-NMR and Mass spectrometry. In order to unambiguously establish the structure–activity relationship for the non-linear optical activity of these compounds, for the first time to our knowledge, we use the femtosecond degenerate four wave mixing (DFWM) technique to quantify and compare the third-order non-linear optical (NLO) activity of all the 15 compounds, under identical conditions. The second harmonics generation (SHG) efficiencies for all the compounds have also been evaluated using the Kurtz-Perry powder method. Among the compounds that we have synthesized here, the ones with A–A–D architecture show the highest NLO activity. Our results show that the NLO activity of a compound with A–A–D architecture can be further enhanced by incorporating a substituent with strong electron withdrawing ability on ring A and strong electron donating substituent on ring B. The results of the in silico studies that we have carried out correlate well with our experimental findings. The compounds (E)-3-(4-(dimethylamino)phenyl)-1-(4-nitrophenyl)prop-2-en-1-one with the compound code (4-N(CH3)2–4′-NO2) and (E)-3-(4-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one with the compound code (4-MeO-4′-NO2) show the highest NLO activity among the compounds we have reported here. Graphical abstract: [Figure not available: see fulltext.]

Convenient Synthesis of Novel Chalcone and Pyrazoline Sulfonamide Derivatives as Potential Antibacterial Agents

Abstract: Novel chalcone sulfonamide derivatives were synthesized starting from benzophenones and aldehydes in 3 steps. Also, (E)-3-(4-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one was converted to different pyrazoline in four steps. The synthesis of s

Direct Reduction of Allylic Alcohols Using Isopropanol as Reductant

The lithium cation-catalyzed direct reduction of allylic alcohols to alkenes using isopropanol as a hydride donor was developed. The hydride transfer of the in situ-generated lithium isopropoxide to an allylic cation is the key process in this transformation. The reaction generates only water and acetone as byproducts, which highlights the synthetic utility of this method. (Figure presented.).

An eco-friendly synthesis of 2-pyrazoline derivatives catalysed by CeCl 3· 7 H 2O

Abstract: 1,3,5-triaryl-2-pyrazoline derivatives were synthesised by a condensation reaction between chalcones and phenyl hydrazine using cerium chloride heptahydrate as a catalyst. All these reactions were carried out in ethyl lactate (70%) as a green solvent. Easy and efficient work up, recyclability of solvent and catalyst are the key merits of this protocol. Graphical Abstract:: SYNOPSIS A facile protocol for the synthesis of 1,3,5-triaryl-2-pyrazolines is described. The solvent ethyl lactate, obtained from renewable sources, is biodegradable. The catalyst CeCl 3· 7 H 2O is a water-tolerant Lewis acid with low toxicity. Easy and clean work up, recyclable solvent and catalyst are merits of the protocol. The reaction works well for all systems giving good yields of the desired products.[Figure not available: see fulltext.].

Synthesis and biological screening of some new 1,5-benzodiazepine derivatives as promising antibacterial and antitubercular agents

In this study, various substituted 1,5-benzodiazepines were synthesized by condensing different substituted chalcones with o-phenylenediamine in methanol using piperidine as a base under refluxing conditions and were obtained in good yield after purificat

Monoamine oxidase inhibitory activity of methoxy-substituted chalcones

The MAO-B inhibitory activity of chalcone (1, 3- diphenyl-2-propen-1-one) based compounds arise from its structural similarity with 1, 4-diphenyl-2-butene, a known MAO-B inhibitor. Based on our previous report, the methoxy-substituted with fluorine containing chalcones are promising reversible MAO-B inhibitors, while in the present study, a series of methoxylated chalcones (C1-C9) bearing substitution on the para position of ring B was synthesized and evaluated for their human monoamine oxidase inhibitory activity. With the exception of (2E)-1-(4-methoxyphenyl)-3-(4-nitrophenyl) prop-2-en-1-one (C7), which is a nonselective inhibitor, the chalcones exhibited competitive, selective, and reversible inhibition of hMAO-B. The most potent compound, (2E)-3-[4-(dimethylamino) phenyl]-1-(4-methoxyphenyl) prop-2-en-1-one (C5), showed the best inhibitory activity towards hMAO-B (IC50 = 0.29 ± 0.011 μM; Ki = 0.14 ± 0.001 μM). The reversibility of MAO-B inhibition by compound C5 was demonstrated by the recovery of enzyme activity after dialysis of mixtures containing enzyme and inhibitor. The reversiblity of C5 was 25.38 ± 1.40 and 92.00 ± 3.87% before and after dialysis, respectively. PAMPA was carried out to evaluate the blood-brain barrier effects of the designated compounds. Moreover, the most potent MAO-B inhibitor, C5, was found to be nontoxic towards cultured hepatic cells at 5 and 25 μM, with 97 and 90% viability. Molecular docking study was performed against hMAO-B to observe the binding site interactions of the lead compound.

Antimicrobial activity of xanthohumol and its selected structural analogues

The objective of this study was to evaluate the antimicrobial activity of structural analogues of xanthohumol 1, a flavonoid compound found in hops (Humulus lupulus). The agar-diffusion method using filter paper disks was applied. Biological tests performed for selected strains of Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria, fungi (Alternaria sp.), and yeasts (Rhodotorula rubra, Candida albicans) revealed that compounds with at least one hydroxyl group - all of them have it at the C-4 position - demonstrated good activity. Our research showed that the strain S. aureus was more sensitive to chalcones than to the isomers in which the heterocyclic ring C is closed (flavanones). The strain R. rubra was moderately sensitive to only one compound: 4-hydroxy-4′-methoxychalcone 8. Loss of the hydroxyl group in the B-ring of 4′-methoxychalcones or its replacement by a halogen atom (-Cl, -Br), nitro group (-NO2), ethoxy group (-OCH2CH3), or aliphatic substituent (-CH3, -CH2CH3) resulted in the loss of antimicrobial activity towards both R. rubra yeast and S. aureus bacteria. Xanthohumol 1, naringenin 5, and chalconaringenin 7 inhibited growth of S. aureus, whereas 4-hydroxy-4′-methoxychalcone 8 was active towards two strains: S. aureus and R. rubra.

Synthesis of new pyrazolyl-1,3-diazabicyclo[3.1.0]hexe-3-ene derivatives

A series of new of photochromic 1,3-diazabicyclo[3.1.0]hex-3-ene derivatives based on the skeleton of five-membered pyrazole moiety have been synthesized and characterized by spectral techniques, as well as their photochromic properties were examined under UV light irradiation in various solutions. All these newly synthesized compounds showed good photochromic properties in the both solution and solid states. The UV-Visible spectral analysis of the corresponding pyrazolyl bicyclic aziridines established structure-photochromic behavior relationships.

Antimycobacterial and anti-inflammatory activities of substituted chalcones focusing on an anti-tuberculosis dual treatment approach

Tuberculosis (TB) remains a serious public health problem aggravated by the emergence of M. tuberculosis (Mtb) strains resistant to multiple drugs (MDR). Delay in TB treatment, common in the MDR-TB cases, can lead to deleterious life-threatening inflammation in susceptible hyper-reactive individuals, encouraging the discovery of new anti-Mtb drugs and the use of adjunctive therapy based on anti-inflammatory interventions. In this study, a series of forty synthetic chalcones was evaluated in vitro for their anti-inflammatory and antimycobacterial properties and in silico for pharmacokinetic parameters. Seven compounds strongly inhibited NO and PGE2 production by LPS-stimulated macrophages through the specific inhibition of iNOS and COX-2 expression, respectively, with compounds 4 and 5 standing out in this respect. Four of the seven most active compounds were able to inhibit production of TNF-α and IL-1β. Chalcones that were not toxic to cultured macrophages were tested for antimycobacterial activity. Eight compounds were able to inhibit growth of the M. bovis BCG and Mtb H37Rv strains in bacterial cultures and in infected macrophages. Four of them, including compounds 4 and 5, were active against a hypervirulent clinical Mtb isolate as well. In silico analysis of ADMET properties showed that the evaluated chalcones displayed satisfactory pharmacokinetic parameters. In conclusion, the obtained data demonstrate that at least two of the studied chalcones, compounds 4 and 5, are promising antimycobacterial and anti-inflammatory agents, especially focusing on an anti-tuberculosis dual treatment approach.

Synthesis of new ferrocenyl 1,3-diazabicyclo[3.1.0]hex-3-ene derivatives

In this work, several new derivatives of ferrocenyl bicylic aziridine photochromic compounds have been prepared from the premade ketoaziridines and ferrocene carboxaldehyde in the presence of ammonium acetate in absolute ethanol via one-pot, three-component reaction. The structures of the newly synthesized compounds were established on the basis of IR, NMR and UV-Vis spectral studies. The newly synthesized compounds exhibit interesting photochromic behavior in the solid phase and solution state. The photochromic behavior of the prepared compounds has been investigated by UV-Visible spectral data.