20972-36-5

Usage

Uses

Used in Pharmaceutical Synthesis:
3-(4-METHYLBENZOYL)ACRYLIC ACID is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties, contributing to advancements in medicinal chemistry.
Used in Organic Material Synthesis:
In the field of materials science, 3-(4-METHYLBENZOYL)ACRYLIC ACID is utilized as a precursor for the creation of organic materials. Its reactivity and structural features enable the production of materials with tailored properties for specific applications.
Used in Organic Chemistry Research:
3-(4-METHYLBENZOYL)ACRYLIC ACID serves as a valuable compound in organic chemistry research. Its unique reactivity and structural attributes make it an interesting subject for studies aimed at understanding reaction mechanisms and developing novel synthetic methodologies.
Used in Drug Development:
3-(4-METHYLBENZOYL)ACRYLIC ACID is used as a starting material in the development of new drugs. Its potential applications in medicinal chemistry include the design of compounds with specific biological activities, targeting various therapeutic areas.
Used in Materials Science:
3-(4-METHYLBENZOYL)ACRYLIC ACID is employed in materials science for the development of new materials with unique properties. Its role in this field is to provide a structural foundation for the creation of materials with applications in various industries, such as electronics, coatings, and adhesives.

InChI:InChI=1/C11H10O3/c1-8-2-4-9(5-3-8)10(12)6-7-11(13)14/h2-7H,1H3,(H,13,14)/b7-6+

Upstream product

• 18103-98-5 3-dimethylamino-1-(4-methyl-phenyl)-2-propen-1-one 
• 122-00-9 para-methylacetophenone 
• 298-12-4 Glyoxilic acid 
• 6000-59-5 glyoxalic acid monohydrate 
• 108-31-6 maleic anhydride 
• 108-88-3 toluene 
• 1777-53-3 1-(p-tolyl)-2-(triphenylphosphoranylidene)ethanone 
• 619-41-0 4-(bromoacetyl)toluene 
• 2689-61-4 (2-oxo-2-p-tolylethyl)triphenylphosphonium bromide 
• 124658-44-2 C₁₃H₁₄O₃ 

Downstream Products

• 122-00-9 para-methylacetophenone 
• 847410-27-9 2,3-dibromo-4-oxo-4-p-tolyl-butyric acid 
• 116274-70-5 4-p-Tolyl-2,3-dihydro-benzo[b][1,4]thiazepine-2-carboxylic acid 
• 155373-13-0 4-(p-toluoyl)-3,4-dihydro-5,6-benzocoumarin 
• 141996-58-9 5-p-Tolyl-2,3-dihydro-furan-2,3-dicarboxylic acid 2-ethyl ester 
• 129887-34-9 γ-(2,4-dihydroxyphenyl)-γ-(4-methylphenyl)-Δ^α,β-butenolide 
• 129887-33-8 γ-(4-hydroxyphenyl)-γ-(4-methylphenyl)-Δ^α,β-butenolide 
• 13863-26-8 9-Carboxy-10-p-toluoyl-Δ^4a(4b)-dodecahydro-phenanthren 
• 39206-68-3 2-(4-Ethyl-phenyl)-4-oxo-4-p-tolyl-butyric acid 
• 103031-73-8 4,4'-dioxo-4,4'-di-p-tolyl-2,2'-pyrrole-2,5-diyl-di-butyric acid 
• 35947-34-3 4-oxo-2-phenyl-4-p-tolyl-butyric acid 
• 102159-25-1 2-(4-methyl-phenacyl)-4-oxo-4-p-tolyl-butyric acid 
• 134949-92-1 (E)-5,5'-di-p-tolyl-[3,3']bifurylidene-2,2'-dione 
• 93727-72-1 3,4-dimethyl-6-(4-methylbenzoyl)cyclohex-3-enecarboxylic acid 

Relevant academic research and scientific papers

Molecular diversity in cyclization of Ugi-products leading to the synthesis of 2,5-diketopiperazines: computational study

Abstract: Ugi-adducts were obtained via a one-pot four-component reaction of divergent aldehydes, amines, aroylacrylic acids and isocyanide in methanol. These products were subjected to intramolecular Michael addition in the presence of K2COsu

Base-Promoted Annulative Difluoromethylenation of Enaminones with BrCF2CO2Et toward 2,2-Difluorinated 2,3-Dihydrofurans

A practical method for the synthesis of 2,2-difluorinated 2,3-dihydrofurans has been established via the [4 + 1] annulation of enaminones and BrCF2CO2Et with Na2CO3 promotion. This new protocol does not employ any transition metal reagent and enables the annulative difluoromethylation by the partial cleavage of the C═C double bond. In addition, the further treatment with hydrochloric acid in one pot leads to β-keto enoic acids (4-oxo-2-butenoic acids) via a formal enaminone C-N carboxylation.

Microwave-assisted synthesis of 4-oxo-2-butenoic acids by aldol-condensation of glyoxylic acid

4-Oxobutenoic acids are useful as biologically active species and as versatile intermediates for further derivatisation. Currently, routes to their synthesis can be problematic and lack generality. Reaction conditions for the synthesis of 4-oxo-2-butenoic

Isocyanide-based MCRs: Diastereoselective cascade synthesis of perfluoroalkylated pyrano[3,4-c]pyrrole derivatives

The highly diastereoselective synthesis of perfluoroalkyl-containing pyrano[3,4-c]pyrroles has been accomplished via a cascade process involving Michael addition, Passerini-type reaction, Mumm rearrangement and an oxo-Diels–Alder reaction. This domino tra

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water

A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is

Design, synthesis and biological evaluation of benzoylacrylic acid shikonin ester derivatives as irreversible dual inhibitors of tubulin and EGFR

In this study, a series of shikonin derivatives combined with benzoylacrylic had been designed and synthesized, which showed an inhibitory effect on both tubulin and the epidermal growth factor receptor (EGFR). In vitro EGFR and cell growth inhibition assay demonstrated that compound PMMB-317 exhibited the most potent anti-EGFR (IC50 = 22.7 nM) and anti-proliferation activity (IC50 = 4.37 μM) against A549 cell line, which was comparable to that of Afatinib (EGFR, IC50 = 15.4 nM; A549, IC50 = 6.32 μM). Our results on mechanism research suggested that, PMMB-317 could induce the apoptosis of A549 cells in a dose- and time-dependent manner, along with decrease in mitochondrial membrane potential (MMP), production of ROS and alterations in apoptosis-related protein levels. Also, PMMB-317 could arrest cell cycle at G2/M phase to induce cell apoptosis, and inhibit the EGFR activity through blocking the signal transduction downstream of the mitogen-activated protein MAPK pathway and the anti-apoptotic kinase AKT pathway; typically, such results were comparable to those of afatinib. In addition, PMMB-317 could suppress A549 cell migration through the Wnt/β-catenin signaling pathway in a dose-dependent manner. Additionally, molecular docking simulation revealed that, PMMB-317 could simultaneously combine with EGFR protein (5HG8) and tubulin (1SA0) through various forces. Moreover, 3D-QSAR study was also carried out, which could optimize our compound through the structure-activity relationship analysis. Furthermore, the in vitro and in vivo results had collectively confirmed that PMMB-317 might serve as a promising lead compound to further develop the potential therapeutic anticancer agents.

Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents

A series of novel (E)-4-oxo-2-crotonamide derivatives were designed and synthesized to find potent antituberculosis agents. All the target compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv(MTB). Results reveal that 4-phenyl moiety at part A and short methyl group at part C were found to be favorable. Most of the derivatives displayed promising activity against MTB with MIC ranging from 0.125 to 4 μg/mL. Especially, compound IIIa16 was found to have the best activity with MIC of 0.125 μg/mL against MTB and with MIC in the range of 0.05–0.48 μg/mL against drug-resistant clinical MTB isolates.

A method for preparing [...] (by machine translation)

The invention discloses a method for synthesizing [...], existing technology with the different is, first of all the toluene with maleic anhydride Friedel-crafts reaction to obtain the 4 - oxo - 4 - (4 - methyl phenyl) - 2 - butenoic, then the same halogen addition to obtain the 3 - halo - 4 - oxo - 4 - (4 - methyl phenyl) - butyric acid, the esterification reaction, the ring, to obtain 2 - (6 - methyl - 2 - P-imidazole [1, 2 - α] pyridine - 3 - yl) acetate, the hydrolysis, acidifying the resulting [...]. The method of the invention, obtaining the high-purity [...], the whole synthetic route less steps, high yield, low cost, less impurities, is suitable for industrial production. (by machine translation)

Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study

Protein kinase B (PknB) is an essential serine/threonine protein kinase required for Mycobacterium tuberculosis (M. tb) cell division and cell-wall biosynthesis. A high throughput screen using PknB identified a (E)-4-oxo-crotonic acid inhibitor, named YH-8, which was used as a scaffold for SAR investigations. A significant improvement in enzyme affinity was achieved. The results indicated that the α,β-unsaturated ketone scaffold and “trans-” configuration are essential for the activity against PknB. And compounds with an aryl group, especially with electron-withdrawing substituents on benzene ring, exhibited four fold potency than that of YH-8.

Application of 4-oxo-2-crotonamide derivative to preparation of bacteriostatic agents

The invention discloses application of a 4-oxo-2-crotonamide derivative to preparation of bacteriostatic agents. The structure of the 4-oxo-2-crotonamide derivative is shown as a formula (I). The 4-oxo-2-crotonamide derivative has a bacteriostatic effect; good antibacterial activity can be realized on methicillin-resistant staphylococcus aureus, methicillin-resistant staphylococcus epidermidis, vancomycin drug-resistant enterococcus faecalis, vancomycin drug-resistant enterococcus faecium, methicillin-sensitive staphylococcus aureus, methicillin-sensitive staphylococcus epidermidis, vancomycin-sensitive enterococcus faecalis and vancomycin-sensitive enterococcus faecium. The formula I is shown in the description.