20432-02-4

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-1-(4-Nitrophenyl)-3-phenyl-2-propene-1-one is used as a chemical intermediate for the synthesis of various pharmaceutical compounds, including flavonoids and dyes, which have potential applications in medicine and healthcare.
Used in Chemical Synthesis:
(2E)-1-(4-Nitrophenyl)-3-phenyl-2-propene-1-one is used as a precursor in chemical synthesis for creating a range of other chemical compounds, highlighting its utility in organic chemistry and the development of new materials.
Used in Cancer Research:
(2E)-1-(4-Nitrophenyl)-3-phenyl-2-propene-1-one is used as a research compound for studying its potential to inhibit the growth of certain cancer cells, which could contribute to the development of new cancer treatments.
Used in Anti-Inflammatory Research:
(2E)-1-(4-Nitrophenyl)-3-phenyl-2-propene-1-one is used in anti-inflammatory research to explore its effects on reducing inflammation, potentially leading to the creation of new anti-inflammatory drugs.

Upstream product

• 17638-55-0 P-phenacyltriphenylphosphonium cation 
• 555-16-8 4-nitrobenzaldehdye 
• 100-52-7 benzaldehyde 
• 100-19-6 (4-nitrophenyl)ethanone 
• 770-37-6 2-(N-benzylidenamino)ethanol 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 17763-80-3 para-nitrophenyl triflate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 581-55-5 benzylidene 1,1-diacetate 
• 72758-64-6 (Z)-4'-nitrochalcone 
• 99-81-0 4-Nitrophenacyl bromide 
• 51246-20-9 1-phenyl-1-iodoethylene 
• 6783-05-7 trans-2-phenylvinylboronic acid 

Downstream Products

• 23893-30-3 1-(4-nitrophenyl)-3-phenyl-2,3-dibromopropan-1-one 
• 95939-26-7 3-(2-morpholin-4-yl-ethylsulfanyl)-1-(4-nitro-phenyl)-3-phenyl-propan-1-one 
• 118757-40-7 5-(4-Nitro-phenyl)-7-phenyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine 
• 121567-86-0 5-(4-Nitro-phenyl)-7-phenyl-4,7-dihydro-tetrazolo[1,5-a]pyrimidine 
• 150356-92-6 2,3-dihydro-7-(4-nitrophenyl)-5-phenyl-2-thioxopyrido<2,3-d>pyrimidin-4(1H)-one 
• 134834-72-3 5-(4-Nitro-phenyl)-7-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylamine 
• 113854-32-3 3-Methyl-6-(4-nitro-phenyl)-1,4-diphenyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine 
• 111336-88-0 3-Methyl-5-(4-nitro-phenyl)-1,7-diphenyl-1,6,7,8-tetrahydro-pyrazolo[3,4-b][1,4]diazepine 
• 13620-59-2 3-Phenyl-1-(4-nitro-phenyl)-4-nitro-butan-1-on 
• 75703-66-1 diethyl 5-(p-nitrophenyl)-3-phenyl-3,4-dihydro-2H-pyrrole-2,2-dicarboxylate 
• 98124-31-3 C₃₆H₂₆NO₃P 
• 54914-77-1 1-(4-nitrophenyl)-3-phenyl-1-propanone 
• 122-78-1 phenylacetaldehyde 
• 62-23-7 4-nitro-benzoic acid 

Relevant academic research and scientific papers

Synthesis and anti-inflammatory activity of three nitro chalcones

The aim of this study was to synthesize three nitro substituted chalcones and to evaluate their anti-inflammatory activity in the model of carrageenan induced edema in rats. The nitro chalcone were prepared by aldol condensation using of mechanical agitation and environmentally friendly solvents with 72-73% yields in approximately 2 h. The three structures were evaluated on biological activity at dose of 200 mg/kg and they showed anti-inflammatory protective effect by both oral and intraperitoneal administration, this effect was time dependent.

Mechanochemical Solvent-Free Suzuki–Miyaura Cross-Coupling of Amides via Highly Chemoselective N?C Cleavage

Although cross-coupling reactions of amides by selective N?C cleavage are one of the most powerful and burgeoning areas in organic synthesis due to the ubiquity of amide bonds, the development of mechanochemical, solid-state methods remains a major challe

Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation

The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.

Mechanochemical Syntheses of N-Containing Heterocycles with TosMIC

A mechanochemical van Leusen pyrrole synthesis with a base leads to 3,4-disubstitued pyrroles in moderate to excellent yields. The developed protocol is compatible with a range of electron-withdrawing groups and can also be applied to the synthesis of oxazoles. Attempts to mechanochemically convert the resulting pyrroles into porphyrins proved to be difficult.

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.]

Organo-catalyzed Michael addition of 2-fluoro-2-arylacetonitriles

An efficient synthesis of a variety of 2-arylacetonitriles containing a fluorinated stereogenic center through organo-catalyzed Michael addition reaction of 2-fluoro-2-arylacetonitriles has been developed. This protocol uses a cheap organocatalyst (DBU) and has a broad substrate scope: α, β-unsaturated ketones, esters, nitriles and sulfones were all successfully reacted. Importantly, water proved to be a good solvent for this reaction.

Recyclable Copper Nanoparticles-Catalyzed Hydroboration of Alkenes and β-Borylation of α,β-Unsaturated Carbonyl Compounds with Bis(Pinacolato)Diboron

Nano-ferrite-supported Cu nanoparticles (Fe-dopamine-Cu NPs) catalyzed anti-Markovnikov-selective hydroboration of alkenes with B2pin2 is reported under mild reaction conditions. This protocol can be applied to a broad range of substrates with high functional group compatibility. In addition, we demonstrated the use of Fe-dopamine-Cu NPs as a catalyst for the β-borylation of α,β-unsaturated ketones and ester, providing alkylboronate esters in up to 98% yield. Reuse of the magnetically recyclable catalyst resulted in no significant loss of activity in up to five reaction runs for both systems. (Figure presented.).

Novel nicotinonitrile-coumarin hybrids as potential acetylcholinesterase inhibitors: design, synthesis, in vitro and in silico studies

Abstract: Alzheimer’s disease is a degenerative brain condition that is the leading cause of dementia affecting millions of people around the world. Therapeutic development has focused on the problem of the loss of basal forebrain cholinergic function, as it is the only evidence responsible for brain neurodegeneration in patients with Alzheimer’s disease. Several attempts to improve cholinergic neurotransmission have been investigated by minimizing synaptic degradation of acetylcholine using acetylcholinesterase inhibitors. In the current study, we explore the designing of a new series of nicotinonitrile-coumarin hybrids as potential acetylcholinesterase inhibitors. The new hybrids were prepared utilizing pyridine-2(1H)-thiones as starting precursors. The in vitro acetylcholinesterase (AChE) inhibitory activities were examined for the new nicotinonitrile-coumarin hybrid molecules, when compared with donepezil as a standard drug with IC50 of 14?nM. Coumarin derivative, linked to 6-(4-nitrophenyl)-4-phenylnicotinonitrile, showed more effective inhibitory activity than the reference donepezil with IC50 of 13?nM. The free radical-scavenging capabilities against DPPH of the new hybrid derivatives were screened. Additionally, their in vitro cytotoxic activities have been tested against various eukaryotic cells. Furthermore, docking study showed excellent interaction between nicotinonitrile-coumarin hybrids and AChE. Graphic abstract: [Figure not available: see fulltext.]

Boosting the catalytic performance of zinc linked amino acid complex as an eco-friendly for synthesis of novel pyrimidines in aqueous medium

Zinc linked amino acid complex, Zn(l-proline)2, is considered as a green catalyst for the synthesis of novel series of pyrimidine derivatives 5a–q. The pyrimidines 5a–q were prepared via two pathways: the first is a one-pot reaction of guanidines 3a–c with aromatic aldehyde 1 and acetophenones 2; and the second one is the reaction of guanidines 3a–c with different chalcones 4a–j in aqueous medium. The simplicity of the operation, the short reaction time, and the high efficiency (97%) are the main advantages of this protocol. Furthermore, the green aspects of this synthetic protocol were further investigated by examining the reusability of Zn(l-proline)2 complex throughout five consecutive cycles without a significant loss of catalytic activity. This new procedure has presented remarkable advantages in terms of safety, simplicity, stability, mild conditions, a short reaction time, excellent yields, and high purities without using any organic solvents.

Rapid umpolung Michael addition of isatin N, N ′-cyclic azomethine imine 1,3-dipoles with chalcones

The umpolung Michael addition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones is reported. The reaction could be finished within a very short time (0.3-2 min), with 3,3-disubstituted oxindole derivatives obtained in moderate to excellent yields with promising dr values. Unusual Michael adducts were obtained in moderate to high yields (26-98%) with low to high diastereoselectivities (0.8: 1 to 8.5: 1 dr). All the synthesized compounds (3, 3′, 4, 5, 5′, 7, 7′, 9 and 9′) were well characterized by FTIR, NMR, and mass spectral analyses and further confirmed by the single-crystal X-ray diffraction analysis of compounds 3aa and 4n.