83072-25-7

Usage

Uses

Used in Pharmaceutical Research:
(4-Methoxyphenyl)(4-methoxybenzylidene)acetic acid is used as an anti-inflammatory agent for its potential to alleviate conditions such as arthritis and other inflammatory disorders. Its ability to reduce inflammation and potentially provide pain relief makes it a promising candidate for further study and development in the pharmaceutical industry.
Used in Synthesis of Complex Chemical Compounds:
In addition to its direct application as an anti-inflammatory agent, (4-Methoxyphenyl)(4-methoxybenzylidene)acetic acid may also serve as a starting material in the synthesis of more complex chemical compounds for pharmaceutical purposes. Its unique structure and properties make it a valuable building block for creating new and innovative medications to address a wide range of health concerns.

InChI:InChI=1/C17H16O4/c1-20-14-7-3-12(4-8-14)11-16(17(18)19)13-5-9-15(21-2)10-6-13/h3-11H,1-2H3,(H,18,19)/b16-11+

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 17274-18-9 sodium 2-(4-methoxyphenyl)acetate 
• 104-01-8 4-Methoxyphenylacetic acid 
• 124-38-9 carbon dioxide 
• 2132-62-9 4,4'-dimethoxydiphenylacetylene 
• 104-47-2 p-methoxybenzylnitrile 
• 63785-34-2 (2Z)-2,3-bis(4-methoxyphenyl)prop-2-enenitrile 
• 219670-51-6 (Z)-2,3-bis(4-methoxyphenyl)acrylaldehyde 
• 50415-62-8 methyl (E)-4-methoxy-α-(4'-methoxyphenylmethylene)benzeneacetate 
• 64-18-6 formic acid 
• 64-19-7 acetic acid 

Downstream Products

• 138744-94-2 1,2-bis(4-methoxyphenyl)-2-oxoethyl acetate 
• 1226-42-2 1,2-bis(4-methoxyphenyl)-1,2-ethanedione 
• 72035-46-2 2,3-bis(4-methoxyphenyl)propanenitrile 
• 52565-72-7 (E)-2-(4-methoxyphenyl)-3-(4-methoxyphenyl)acrylonitrile 
• 380914-92-1 methyl 2,3-bis(4-methoxyphenyl)propionate 
• 693775-74-5 (E)-2,3-bis(4-methoxyphenyl)acrylamide 
• 1268468-00-3 (E)-2,3-bis(4-methoxyphenyl)prop-2-en-1-ol 
• 50415-62-8 methyl (E)-4-methoxy-α-(4'-methoxyphenylmethylene)benzeneacetate 
• 93330-31-5 4-Methoxy-α-<4-methoxy-phenyl>-cis-zimtsaeurechlorid 
• 693775-75-6 (Z)-2,3-Bis-(4-methoxy-phenyl)-acrylic acid methyl ester 
• 1025967-67-2 (E)-2,3-Bis-(4-methoxy-phenyl)-acrylic acid 4-nitro-phenyl ester 
• 93330-31-5 4-Methoxy-α-<4-methoxy-phenyl>-trans-zimtsaeurechlorid 

Relevant academic research and scientific papers

The synergistic copper/ppm Pd-catalyzed hydrocarboxylation of alkynes with formic acid as a CO surrogate as well as a hydrogen source: An alternative indirect utilization of CO2

An unprecedented strategy has been developed involving the earth-abundant Cu-catalyzed hydrocarboxylation of alkynes with HCOOH to (E)-acrylic derivatives with high regio- and stereoselectivity via synergistic effects with ppm levels of a Pd catalyst. Both symmetrical and unsymmetrical alkynes bearing various functional groups were successfully hydrocarboxylated with HCOOH, and the modification of a pharmaceutical molecule exemplified the practicability of this process. This protocol employs HCOOH as both a CO surrogate and hydrogen donor with 100% atom economy and it can be viewed as an alternative approach for indirect CO2 utilization. Mechanistic investigations indicate a Cu/ppm Pd cooperative catalysis mechanism via alkenylcopper species as potential intermediates formed from Cu-hydride active catalytic species with HCOOH as a hydrogen source. This bimetallic system involving inexpensive Cu and trace Pd provides a reliable and efficient hydrocarboxylation method to access industrially useful acrylic derivatives with HCOOH as a hydrogen source, and it provides novel clues for optimizing other Cu-H-related co-catalytic systems.

Electrocatalytic asymmetric hydrogenation of α,β-unsaturated acids in a PEM reactor with cinchona-modified palladium catalysts

We have developed an electrocatalytic asymmetric hydrogenation reaction using a proton-exchange membrane (PEM) reactor that employs a polymer electrolyte fuel cell and industrial electrolysis technologies. Reasonable enantioselectivities and excellent current efficiencies were obtained in the asymmetric hydrogenation of α-phenylcinnamic acid under mild conditions without adding a supporting electrolyte. The current density was crucial to achieving the improved results observed.

Decarboxylation of α,β-unsaturated aromatic lactones: Synthesis of: E-ortho -hydroxystilbenes from 3-arylcoumarins or isoaurones

A simple and environmentally friendly strategy for the synthesis of E-ortho-hydroxystilbenes has been established. Two kinds of α,β-unsaturated aromatic lactones, i.e. the 3-arylcoumarins and the isoaurones, could both readily undergo a cascade hydrolyzation/decarboxylation reaction in the presence of KOH in ethylene glycol to afford the desired E-ortho-hydroxystilbenes in moderate to high yields.

Cp2TiCl2-catalyzed hydrocarboxylation of alkynes with CO2: formation of α,β-unsaturated carboxylic acids

Cp2TiCl2-catalyzed hydrocarboxylation of alkynes with CO2 (atmospheric pressure) has been reported. A range of alkynes were transformed to the corresponding α,β-unsaturated carboxylic acids in high yields with high regioselectivity. The reaction proceeded with hydrotitanation, transmetalation, and subsequently carboxylation with CO2

An evaluation of Minor Groove Binders as anti-lung cancer therapeutics

A series of 47 structurally diverse MGBs, derived from the natural product distamycin, was evaluated for anti-lung cancer activity by screening against the melanoma cancer cell line B16-F10. Five compounds have been found to possess significant activity, more so than a standard therapy, Gemcitabine. Moreover, one compound has been found to have an activity around 70-fold that of Gemcitabine and has a favourable selectivity index of greater than 125. Furthermore, initial studies have revealed this compound to be metabolically stable and thus it represents a lead for further optimisation towards a novel treatment for lung cancer.

Preparation method of alpha, beta-unsaturated carboxylic acid compounds

The invention provides a preparation method of alpha, beta-unsaturated carboxylic acid compounds. The method is characterized in that compounds represented by formula (I) react with formic acid in the presence of a nickel-containing catalyst, a phosphine ligand and an organic solvent to obtain the alpha, beta-unsaturated carboxylic acid compounds represented by formula (II), wherein R1 and R2 are respectively independently selected from H, C1-C30 alkyl groups, C1-C30 substituted alkyl groups, C1-C30 alkenyl groups, C1-C30 substituted alkenyl groups, C6-C30 aryl groups and C6-C30 substituted aryl groups. Compared with the prior art, the method adopting formic acid as a carboxylation reagent has the advantages of low price, safety, stability, low toxicity, high yield, simple operation, good economy, avoiding of use of precious metal catalysts and toxic gas carbon monoxide, meeting of requirements of environmentally friendly compounds, wide function group compatibility, high conversion rate and industrial synthesis values.

Discovery of a new chemical series of BRD4(1) inhibitors using protein-ligand docking and structure-guided design

Bromodomains are key transcriptional regulators that are thought to be druggable epigenetic targets for cancer, inflammation, diabetes and cardiovascular therapeutics. Of particular importance is the first of two bromodomains in bromodomain containing 4 protein (BRD4(1)). Protein-ligand docking in BRD4(1) was used to purchase a small, focused screening set of compounds possessing a large variety of core structures. Within this set, a small number of weak hits each contained a dihydroquinoxalinone ring system. We purchased other analogs with this ring system and further validated the new hit series and obtained improvement in binding inhibition. Limited exploration by new analog synthesis showed that the binding inhibition in a FRET assay could be improved to the low μM level making this new core a potential hit-to-lead series. Additionally, the predicted geometries of the initial hit and an improved analog were confirmed by X-ray co-crystallography with BRD4(1).

Synthesis and in-vitro cytotoxicity of (E)-N,2,3-triarylacrylamide derivatives as analogs of combretastatin A-4

A new series of (E)-N,2,3-triarylacrylamide derivatives were designed and synthesized as potent anticancer agents. Cytotoxicity of the 26 target compounds was evaluated in vitro against six cancer cell lines (HCT116, A549, MDA-MB-468, HepG2, SKNMC and SK-OV-3) by Sulforhodamine B colorimetric assay. The most promising compound, 4h, was as potent as the reference drug cisplatin (DDP). Preliminary structure-activity relationship (SAR) data provided guidance for further design and discovery of (E)-N,2,3-triarylacrylamide scaffold anticancer agents.

Surface enhanced Raman spectroscopic (SERS) behavior of substituted propenoic acids used in heterogeneous catalytic asymmetric hydrogenation

The strength and geometry of adsorption of substituted propenoic acids on silver surface were studied by means of surface enhanced Raman spectroscopy (SERS) using silver sol. Based on their SERS behavior, two classes of phenylpropenoic acids studied were distinguished. The first class of propenoic acids (atropic acid, (E)-2,3-diphenylpropenoic acid, (E)-2-(2-methoxyphenyl)-3-phenylpropenoic acid, (E)-2,3-di-(4-methoxyphenyl)phenylpropenoic acid and (E)-2-(2-methoxyphenyl)-3-(4-fluorophenyl)propenoic acid) has shown strong charge transfer (CT) effect. We suggest bidentate carboxyl bonded species based on the SERS enhanced bands of νCOO- around 1394 cm-1 and νC-C of the -C-COO- moiety at 951 cm-1. In these series the plane of the α-phenyl group (γCH out-of-plane vibrations at 850-700 cm-1) is almost parallel to the silver surface, while the β-phenyl group is in tilted position depending on the type and the position of substituent(s) showing strong SERS enhanced bands of νCC + βCH (in-plane mode) at 1075 cm-1, νCC (ring breathing mode, in-plane) at 1000 cm-1 and γCCC (out-of-plane mode) around 401 cm-1. The other class of propenoic acids (cinnamic acid, (E)-2-phenyl-3-(4-methoxyphenyl)propenoic acid) has shown weak electromagnetic (EM) enhancement (CC bands is enhanced in cinnamic acid). In this case no significant carboxyl enhancement was observed, so we suggest that adsorbed species lie parallel to the surface. The two types of adsorption can be related to the dissociation ability of the carboxylic group. In the first case the carboxylic H dissociates, while in the second case it does not, as indicated also by the characteristic νCO band at 1686 cm-1 in the FT-Raman spectra of methanolic solutions.

Ni-Catalyzed Regioselective Hydrocarboxylation of Alkynes with CO2 by Using Simple Alcohols as Proton Sources

A mild and user-friendly Ni-catalyzed regioselective hydrocarboxylation of alkynes with CO2 (1 bar) is described. This protocol is characterized by a wide scope while obviating the need for sensitive organometallic species and by an unprecedented regioselectivity pattern using simple alcohols as proton sources.