52182-14-6

Usage

InChI:InChI=1/C17H16O3/c1-19-15-9-7-14(8-10-15)17(18)11-6-13-4-3-5-16(12-13)20-2/h3-12H,1-2H3/b11-6+

Upstream product

• 3654-50-0 3-(3-hydroxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one 
• 74-88-4 methyl iodide 
• 591-31-1 3-methoxy-benzaldehyde 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 1226526-58-4 2-(benzo[d]thiazol-2-ylsulfonyl)-1-(4-methoxyphenyl)ethanone 
• 20912-79-2 4-methoxyphenacylidene dimethylsulphurane 
• 19350-71-1 N'-(3-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 7099-91-4 p-methoxybenzoylformic acid 
• 6099-04-3 3-methoxycinnamic acid 
• 15851-92-0 (E)-3-methoxycinnamoyl chloride 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 123-11-5 4-methoxy-benzaldehyde 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 

Downstream Products

• 1188386-75-5 3-(4-bromo-3-methoxyphenyl)-1-(4-methoxyphenyl)allylketone 
• 1092964-13-0 5-(3-methoxyphenyl)-3-(4-methoxyphenyl)-1H-pyrazole 
• 1122659-71-5 2,3-dibromo-1-(4-methoxyphenyl)-3-(3-methoxyphenyl)propane-1-one 
• 1380395-74-3 3-(3-methoxyphenyl)-1-(4-methoxyphenyl)pent-4-en-1-ol 
• 1380395-69-6 3-(3-methoxyphenyl)-1-(4-methoxyphenyl)pent-4-en-1-one 
• 63144-61-6 1-methoxy-3-(3-(4-methoxyphenyl)propyl)benzene 
• 169803-91-2 4-(4-Methoxy-phenyl)-2-(3-methoxy-phenyl)-4-oxo-butyric acid methyl ester 
• 169803-90-1 4-(4-Methoxy-phenyl)-2-(3-methoxy-phenyl)-4-oxo-butyronitrile 
• 75849-21-7 1-(4-methoxyphenyl)-3-(3-methoxyphenyl)propan-1-ol 
• 75849-31-9 7-methoxy-1-(4-methoxyphenyl)indan 
• 75849-32-0 5-methoxy-1-(4-methoxyphenyl)indan 
• 75849-24-0 1-(4-methoxyphenyl)-3-(3-methoxyphenyl)prop-1-ene 
• 74973-44-7 3-(4-methoxybenzoyl)-1-(3-methoxyphenyl)propanol 
• 75849-20-6 3-(3-methoxyphenyl)-1-(4-methoxyphenyl)propan-1-one 

Relevant academic research and scientific papers

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.

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.

Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products

A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and a synthetically useful morphinan alkaloid precursor.

Hansch’s analysis application to chalcone synthesis by Claisen–Schmidt reaction based in DFT methodology

Chalcones are bioactive compounds obtained from either natural sources or synthetic procedures and widely used due to their several biological properties. The most common experimental methodology in obtaining these compounds is Claisen–Schmidt reaction, which is a particular type of aldolic condensation. In this work, we have synthesized 23 chalcones and by density functional theory (DFT) calculation, we have studied the difference in reactivity of the several benzaldehydes and their effects on the yield of this reaction. From molecular orbital descriptors were obtained two quantitative structure–reactivity relationship (QSRR) models based on Hansch’s analysis. The results of this study showed that, for the most benzaldehydes (15 of 23 compounds), their reactivity was correlated with LUMO energy and global Electrophilicity Index (ω) values, which are determined in the first step of Claisen–Schmidt condensation mechanism (nucleophilic addition). Likewise, for the smallest group of benzaldehydes, their reactivity was related to their HOMO and ΔL???H (LUMO???HOMO) energies, which were determined in the second step of the mechanism (trans-elimination). This is the first report of a QSRR model analyzing the yield of chalcone synthesis based on DFT methodology.

Biological evaluation and synthesis of new pyrimidine-2(1H)-ol/-thiol derivatives derived from chalcones using the solid phase microwave method

Twenty-five new hydroxy- and methoxy-substituted 4,6-diarylpyrimidin-2(1H)-ol (20–34) and 4,6-diarylpyri-midine-2(1H)-thiol derivatives (35–44) were synthesized from the reaction of the corresponding 1,3-diaryl-2-propene-1-one compounds (1–19) with urea or thiourea using the solid-phase microwave method. All the new synthetic compounds (20–44) were evaluated with regard to their α-glucosidase activity. However, only compounds 22–25, 27, 31, 34, 35, 37, and 40 exhibited a greater inhibitory effect than standard acarbose. The IC50 values of the active compounds ranged between 2.36 and 13.34 μM. The 25 new compounds were also screened for their in vitro pancreatic lipase activity and compounds 20–27 and 35–39 were found to be active. Of these compounds 26, 27, and 39 exhibited the best antilipase activities at concentrations of 0.40 ± 0.06, 0.26 ± 0.07, and 0.29 ± 0.026 μM. All the new compounds (20–44) were evaluated for their in vitro antimicrobial activity for nine test microorganisms. Compounds 20–24 and 35–39 were determined to possess a significant broad spectrum against the gram-positive bacteria Escherichia faecalis, Staphylococcus aureus, and Bacillus cereus among the tested bacterial agents. Compounds 20–24 and 35–39 exhibit the best activity against Mycobacterium smegmatis, with minimum inhibitory concentrations of 62.5–500 μg/mL, indicating their potential use as antituberculous agents.

Imidazole-triazine type compound and preparation method and application thereof

The invention provides an imidazole-triazine type compound which is shown as the formula 3 in the description and a preparation method and application thereof. The method comprises the steps that a triazine compound and an alpha,beta-unsaturated ketone type compound are mixed and added into a solvent, under the existence of a metal copper catalyst and an oxidizing material, the mixed solution is stirred and reacts 5-20 hours under the temperature of 60-150 DEG C, after the reaction is finished, the reacted solution is subjected to post processing, and the imidazole-triazine type compound which is shown as the formula 3 is obtained; the metal copper catalyst is halogenide of the copper or a copper salt; the oxidizing material is a halogen elementary substance. The imidazole-triazine type compound can be applied to prepare antibacterial drugs or antibacterial agents, and the preferred antibacterial drugs are the drugs which inhibit activity of escherichia coli.

Synthesis of a series of unsaturated ketone derivatives as selective and reversible monoamine oxidase inhibitors

We have synthesized three categories of α,β-unsaturated carbonyl derivatives and evaluated their MAO-A and MAO-B inhibitory activities. Among them, compound 10b including α,β-unsaturated ketone group showed the most potent and selective MAO-B inhibitory activity (IC50 human MAO-B 16 nM, >6000-fold selective vs MAO-A) and compound 10b exhibited good reversibility compared with selegiline, a well-known irreversible MAO-B inhibitor. However, both α,β-unsaturated amide and ester derivatives exhibited weaker MAO-B inhibition potencies. The docking studies provided insights into the possible binding modes and the key interaction sites of the synthesized MAO-B inhibitors.

ANTI-INVASIVE COMPOUNDS

The present invention relates to the field of anti-invasive compounds and methods for predicting the anti-invasive activity of said compounds, as well as their use in the prevention and/or treatment of diseases associated with undesired cell invasion; in particular, this invention relates to the field of anti-invasive chalcone-like compounds.

Silver-catalyzed double-decarboxylative cross-coupling of α-keto acids with cinnamic acids in water: A strategy for the preparation of chalcones

A silver-catalyzed double-decarboxylative protocol has been proposed for the construction of chalcone derivatives via cascade coupling of substituted α-keto acids with cinnamic acids under the mild aqueous conditions. The developed method for constructing C-C bonds via double-decarboxylative reactions is efficient, practical, and environmentally benign by using the readily available starting materials. It should provide a promising synthesis candidate for the formation of diverse and useful chalcone derivatives in the fields of synthetic and pharmaceutical chemistry.

4-Fluoro-3′,4′,5′-trimethoxychalcone as a new anti-invasive agent. From discovery to initial validation in an in vivo metastasis model

Invasion and metastasis are responsible for 90% of cancer-related mortality. Herein, we report on our quest for novel, clinically relevant inhibitors of local invasion, based on a broad screen of natural products in a phenotypic assay. Starting from micromolar chalcone hits, a predictive QSAR model for diaryl propenones was developed, and synthetic analogues with a 100-fold increase in potency were obtained. Two nanomolar hits underwent efficacy validation and eADMET profiling; one compound was shown to increase the survival time in an artificial metastasis model in nude mice. Although the molecular mechanism(s) by which these substances mediate efficacy remain(s) unrevealed, we were able to eliminate the major targets commonly associated with antineoplastic chalcones.