41564-65-2

Usage

Uses

Used in Organic Synthesis:
(2E)-1-(4-methoxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one is used as a building block for the synthesis of more complex organic molecules. Its α, β-unsaturated ketone structure allows for various chemical reactions, making it a versatile compound in organic synthesis.
Used in Pharmaceutical Research:
(2E)-1-(4-methoxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one is used as a starting material for the development of new pharmaceuticals. Its aromatic substituents and unique structure make it a promising candidate for the creation of novel drug molecules.
Used in Agrochemical Development:
(2E)-1-(4-methoxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one is also used as a starting material for the development of new agrochemicals. Its structural features and potential reactivity make it a valuable compound for the creation of innovative agrochemical products.

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 138711-20-3 1-(4-Methoxy-phenyl)-2-[2-(4-methoxy-phenyl)-2-oxo-ethanesulfinyl]-ethanone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 100-07-2 4-methoxy-benzoyl chloride 
• 51410-44-7 1-(4-methoxylphenyl)-2-propen-1-ol 
• 5720-05-8 4-methylphenylboronic acid 
• 589-18-4 4-Methylbenzyl alcohol 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 
• 196862-13-2 2-(1H-1,2,3-benzotriazol-1-yl)-1-<4-(methyloxy)phenyl>-2-(4-methylphenyl)-3-(trimethylsilyl)propan-1-one 
• 15851-89-5 (E)-p-methylcinnamoyl chloride 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 7099-91-4 p-methoxybenzoylformic acid 
• 20912-79-2 4-methoxyphenacylidene dimethylsulphurane 

Downstream Products

• 132808-72-1 4-(4-Methoxy-phenyl)-6-p-tolyl-5,6-dihydro-1H-pyrimidine-2-thione 
• 127394-79-0 2-methoxy-6-(4-methoxy-phenyl)-4-p-tolyl-nicotinonitrile 
• 1132907-10-8 (2-hydroxy-2-(4-methoxyphenyl)-4,5-di-p-tolylcyclopentyl)(4-methoxyphenyl)methanone 
• 898807-86-8 C₂₅H₂₃NO₂ 
• 519149-78-1 7-(4-methoxyphenyl)-1,3-dimethyl-5-p-tolylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione 
• 1234670-67-7 3-(4-methoxyphenyl)-3-oxo-1-p-tolylpropyl diethylcarbamodithioate 
• 1260620-88-9 6-(4-methoxyphenyl)-3-methyl-1-phenyl-4-p-tolyl-1H-pyrazolo[3,4-b]pyridine 
• 153332-15-1 3-(4-methoxyphenyl)-5-(p-tolyl)-2-pyrazoline-1-carbothioamide 
• 1174918-68-3 C₂₃H₂₁NOS 
• 287961-67-5 1-(4-methoxyphenyl)-3-(phenylamino)-3-p-tolylpropan-1-one 
• 1346451-23-7 1-(4-methoxyphenyl)-3-(phenylamino)-3-p-tolylpropan-1-one 
• 1350308-47-2 (4-methoxyphenyl)(2-(2-nitrophenyl)-5-(p-tolyl)-2H-1,2,3-triazol-4-yl)methanone 
• 106511-65-3 3-(4-methylphenyl)-1-(4’-methoxyphenyl)propan-1-one 

Relevant academic research and scientific papers

Method using Ti (III) complex catalytic alkyne selective hydrogenation reduction to prepare chalcone compounds

The invention discloses a method for preparing chalcone compounds through selective hydrogenation of Ti (III) complexes to prepare chalcone compounds, wherein zinc powder is used as a catalyst, zinc powder is a reducing agent, triethylamine hydrochloride is a proton source, and an alkyne and triethylamine hydrochloride are subjected to radical selective addition reaction under the protection of inert gas to generate chalcone compounds. The reaction condition is mild, the operation is simple, the reaction time is short, the reaction product is single, the atom economy is high, and only the product needs to be separated by simple column chromatography after the reaction is finished. The chalcone compound has wide biological activity and medicinal value.

Alkene Synthesis by Photo-Wolff-Kischner Reaction of Sulfur Ylides and N-Tosylhydrazones

A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity. A series of mechanistic studies support that the reaction should proceed through a radical-carbanion crossover pathway, specifically involving addition of photo-generated sulfur ylide radical cations to N-tosylhydrazones to form carbanions and subsequent Wolff-Kischner process.

Combined 3D-QSAR and docking analysis for the design and synthesis of chalcones as potent and selective monoamine oxidase B inhibitors

Monoamine oxidases (MAOs) are important targets in medicinal chemistry, as their inhibition may change the levels of different neurotransmitters in the brain, and also the production of oxidative stress species. New chemical entities able to interact selectively with one of the MAO isoforms are being extensively studied, and chalcones proved to be promising molecules. In the current work, we focused our attention on the understanding of theoretical models that may predict the MAO-B activity and selectivity of new chalcones. 3D-QSAR models, in particular CoMFA and CoMSIA, and docking simulations analysis have been carried out, and their successful implementation was corroborated by studying twenty-three synthetized chalcones (151–173) based on the generated information. All the synthetized molecules proved to inhibit MAO-B, being ten out of them MAO-B potent and selective inhibitors, with IC50 against this isoform in the nanomolar range, being (E)-3-(4-hydroxyphenyl)-1-(2,2-dimethylchroman-6-yl)prop-2-en-1-one (152) the best MAO-B inhibitor (IC50 of 170 nM). Docking simulations on both MAO-A and MAO-B binding pockets, using compound 152, were carried out. Calculated affinity energy for the MAO-A was +2.3 Kcal/mol, and for the MAO-B was ?10.3 Kcal/mol, justifying the MAO-B high selectivity of these compounds. Both theoretical and experimental structure–activity relationship studies were performed, and substitution patterns were established to increase MAO-B selectivity and inhibitory efficacy. Therefore, we proved that both 3D-QSAR models and molecular docking approaches enhance the probability of finding new potent and selective MAO-B inhibitors, avoiding time-consuming and costly synthesis and biological evaluations.

Design and synthesis of quinoline-pyrimidine inspired hybrids as potential plasmodial inhibitors

Presently, artemisinin-based combination therapy (ACT) is the first-line therapy of Plasmodium falciparum malaria. With the emergence of malaria parasites that are resistant to ACT, alternative antimalarial therapies are urgently needed. In line with this

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.

Synthesis, characterization, molecular docking and in vitro anticancer activity of 3-(4-methoxyphenyl)-5-substituted phenyl-2-pyrazoline-1-carbothioamide

In the present study, eight numbers of new 3-(4-methoxy phenyl)-5-substituted phenyl-2-pyrazoline-1-carbothioamide (5a-h) have been synthesized from 1-(4-methoxy phenyl)-3-(substituted phenyl)-prop-2-en-1-one (3a-h) and structurally characterized by using FT-IR,1H NMR,13C NMR, Mass and Elemental analysis. The synthesized molecules were biologically eval-uated for their in vitro anticancer activity against human breast adenocar-cinoma (MCF-7), liver cancer (Hep-G2) and leukaemia cancer (K-562) cell line using Sulforhodamine B (SRB) bioassay technique. From the all synthesized compounds 5a, 5c, 5d, and 5e exhibited potent anticancer activity (GI50= 50=44.5μg/ml) and Adriamycin (ADR) (GI50= 10μg/ml) on MCF-7 cell lines. Besides this, all the synthesized compounds have exhibited moderate activity against human liver cancer (Hep-G2) and leukaemia cancer (K-562) cell lines. In addition, molecular docking studies were also explored in order to study the probable binding specificity into the active site of Epidermal Growth Factor Receptor tyrosine kinase (EGFR) (PDB ID: 1M17) using Molegro Virtual Docker Evaluation 2013 6.0.1 (MVD). Based on the molecular docking result, it was found that compound 5a exhibited the best interaction with the above target (i.e., EGFR) by interacting with specific amino acid residues such as: Thr 766, Gin 767, Thr 830, Cys 575, Ala 719 and Met 769.

Design, synthesis, and SAR study of novel 4,5-dihydropyrazole-Thiazole derivatives with anti-inflammatory activities for the treatment of sepsis

Systemic inflammatory response syndrome is a major feature of sepsis which is one of the major causes of death worldwide. It has been reported that 3,5-diaryl-4,5-dihydropyrazole and thiazole derivatives have many biological functions, especially in the aspect of anti-inflammation. According to the strategy of pharmacophore combination, we introduced thiazole moiety into dihydropyrazole skeleton to design and synthesize a novel series of 2-(3,5-diphenyl-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole derivatives, and evaluated their anti-inflammatory activities for sepsis treatment. Preliminary structure?activity relationship (SAR) analysis was conducted by their inhibitory activities against nitric oxide (NO) release in LPS-induced RAW264.7 cells, and the optimal compound E26 exhibited more potent anti-inflammatory activity than the positive control treatment indomethacin and dexamethasone. In further mechanism study, our results showed that compound E26 significantly suppressed the production of interleukin-1β (IL-1β), tumor necrosis factor-α (TNF-α), NO and inhibited the expressions of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2) through blocking MAPKs signaling pathway. In addition, in vivo administration of compound E26 resulted in a significant improvement of LPS-induced sepsis in C57BL/6J mice, with reducing toxicity in multiple organs. Taken together, this study demonstrated the compound E26 could be a promising agent for the treatment of sepsis.

Antiproliferative effects of chalcones on T cell acute lymphoblastic leukemia-derived cells: Role of PKCβ

In this study, a series of 20 chalcone derivatives was synthesized, and their antiproliferative activity was tested against the human T cell acute lymphoblastic leukemia-derived cell line, CCRF-CEM. On the basis of the structural features of the most active compounds, a new library of chalcone derivatives, according to the structure–activity relationship design, was synthesized, and their antiproliferative activity was tested against the same cancer cell line. Furthermore, four of these derivatives (compounds 3, 4, 8, 28), based on lower IC50 values (between 6.1 and 8.9 μM), were selected for further investigation regarding the modulation of the protein expression of RACK1 (receptor for activated C kinase), protein kinase C (PKC)α and PKCβ, and their action on the cell cycle level. The cell cycle analysis indicated a block in the G0/G1 phase for all four compounds, with a statistically significant decrease in the percentage of cells in the S phase, with no indication of apoptosis (sub-G0/G1 phase). Compounds 4 and 8 showed a statistically significant reduction in the expression of PKCα and an increase in PKCβ, which together with the demonstration of an antiproliferative role of PKCβ, as assessed by treating cells with a selective PKCβ activator, indicated that the observed antiproliferative effect is likely to be mediated through PKCβ induction.

Synthesis of sulfonamides bearing 1,3,5-triarylpyrazoline and 4-thiazolidinone moieties as novel antimicrobial agents

Two series of sulfonamides were synthesized from 4-hydrazinylben-zenesulfonamide as the key starting material. 1,3,5-Triarylpyrazoline sulfonamides (2a-i) were obtained by cyclocondensation of various chalcones in 53-64 % yields, while 4-thiazolidinone derivatives (4a-e) were synthesized by cyclocondensation between mercaptoacetic acid and different phenylhydrazones in 43-62 % yields. The synthesized compounds were characterized based on FTIR, 1H-NMR, 13C-NMR and HRMS data. The sulfonamides were evaluated for their in vitro antimicrobial activities against four bacterial strains (E. coli, P. aeruginosa, B. subtillis and S aureus), two filamentous fungal strains (A. Niger and F. oxysporum) and two yeast strains (C. albicans and S. cerevisiae). Seven pyrazolines, 2a-c and 2e-h, exhibited significant inhibition of different microbial strains. Among them, compound 2b displayed good antifungal activity against A. Niger (MIC value at 12.5 μg mL-1) over the reference drug.

Synthesis and characterization of new 4,5-dihydropyrazol-1-yl derivatives

In this study, first, a series of chalcone compounds S1–S6 were synthesized from various acetophenone derivatives (acetophenone, p-methyl acetophenone, and p-methoxy acetophenone) and aromatic aldehyde derivatives (benzaldehyde, p-methyl benzaldehyde, and p-methoxy benzaldehyde) by the Claisen–Schmidt condensation reaction. These S1–S6 compounds were then used in the preparation of 4,5-dihydropyrazol-1-yl derivatives S7–S15. Finally, four new compounds S16–S19 were synthesized from compound (S7, S8, S9, and S12) and 2,4-dinitrophenylhydrazine. Therefore, three known and ten new heterocyclic compounds were synthesized and completely characterized using 1H NMR, 13C NMR, IR, and elemental analysis.