20972-38-7

Usage

Uses

Used in Pharmaceutical Research and Development:
(2E)-4-(4-bromophenyl)-4-oxobut-2-enoic acid is utilized as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications. Its role in the creation of novel compounds is crucial for advancing the field of medicinal chemistry.
Used in Organic Synthesis:
In the realm of organic synthesis, (2E)-4-(4-bromophenyl)-4-oxobut-2-enoic acid is employed as a versatile building block for the construction of complex organic molecules. Its reactivity and structural features make it a valuable component in the synthesis of a wide range of organic compounds.
Used in Drug Development for Anti-inflammatory and Analgesic Properties:
(2E)-4-(4-bromophenyl)-4-oxobut-2-enoic acid is used as a potential candidate for the development of new drugs with anti-inflammatory and analgesic properties. Its inherent ability to reduce inflammation and alleviate pain positions it as a promising agent for the treatment of various conditions that require such therapeutic effects.
Used in Chemical Intermediates for Synthesis of Other Compounds:
(2E)-4-(4-bromophenyl)-4-oxobut-2-enoic acid is also used as a chemical intermediate in the synthesis of other organic compounds, showcasing its utility beyond the pharmaceutical industry. Its role in the synthesis of various compounds underscores its importance in the broader field of chemistry.

Upstream product

• 108-31-6 maleic anhydride 
• 108-86-1 bromobenzene 
• 67-66-3 chloroform 
• 35513-39-4 β-(4-bromobenzoyl)acrylic acid 
• 7647-01-0 hydrogenchloride 
• 857229-07-3 4-(4-bromo-phenyl)-2-methoxy-4-oxo-butyric acid 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 90766-44-2 4-oxo-4-(4-bromo-phenyl)-cis-crotonic acid amide 
• 99-90-1 para-bromoacetophenone 
• 298-12-4 Glyoxilic acid 
• 6000-59-5 glyoxalic acid monohydrate 
• 81008-11-9 C₁₀H₉BrO₄ 
• 85060-86-2 2,2-dimethyl-5-(p-bromophenacyl)-1,3-dioxane-4,6-dione 

Downstream Products

• 32149-27-2 trans-methyl-4-(4-bromophenyl)-4-oxobut-2-enoate 
• 6340-79-0 4-oxo-4-(4-bromophenyl)butanoic acid 
• 35513-39-4 β-(4-bromobenzoyl)acrylic acid 
• 29509-18-0 4-(4-bromo-phenyl)-2-methoxy-4-oxo-butyric acid methyl ester 
• 7477-66-9 4-oxo-4-(4-bromo-phenyl)-trans-crotonic acid-chloride 
• 857229-07-3 4-(4-bromo-phenyl)-2-methoxy-4-oxo-butyric acid 
• 118540-49-1 2-benzoylthio-3-(4-bromobenzoyl)propionic acid 
• 118540-48-0 3-(4-bromobenzoyl)-2-propionylthiopropionic acid 
• 118540-47-9 3-(4-bromobenzoyl)-2-ethylthiopropionic acid 
• 97220-73-0 2-acetylthio-3-(4-bromobenzoyl)propionic acid 
• 316174-45-5 4-(p-bromophenyl)-4-oxo-2-(4-antipyrinyl)butanoic acid 

Relevant academic research and scientific papers

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

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.

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.

MITOCHONDRION LOCALIZED FLUORESCENT COMPOUND

PROBLEM TO BE SOLVED: To provide a fluorescent compound capable of labeling mitochondrion more easily with high sensitivity and specificity. SOLUTION: There is provided a fluorescent composition for fluorescent dyeing mitochondrion containing a compound r

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.

Chemistry of the Synthetic Strigolactone Mimic GR24

This research paper describes a second-generation, enantioselective synthesis of (+)-GR24. This new strategy circumvents the need for ozonolysis, which may not be suitable for reactions performed on scale. This flexible new approach is then used to synthesise a novel bromo-GR24 analogue. Finally, the optimal solvent for making GR24 stock solutions is identified.

Hydrogen-bond-directed formal [5 + 1] annulations of oxindoles with ester-linked bisenones: Facile access to chiral spirooxindole δ-lactones

A novel bifunctional thiourea catalyzed formal [5 + 1] cycloaddition of oxindoles and ester-linked bisenones was successfully developed. This strategy involves two sequential Michael additions, leading to spirooxindole δ-lactones with three contiguous ste

(E)-4-Aryl-4-oxo-2-butenoic acid amides, chalcone-aroylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization

Antiproliferative activity of twenty-nine (E)-4-aryl-4-oxo-2-butenoic acid amides against three human tumor cell lines (HeLa, FemX, and K562) is reported. Compounds showed antiproliferative activity in one-digit micromolar to submicromolar concentrations.