5711-41-1

Usage

Uses

Used in Pharmaceutical Synthesis:
3-(4-Methoxybenzoyl)acrylic acid is used as an intermediate in the synthesis of various organic compounds and pharmaceuticals. Its unique chemical structure allows it to participate in a wide range of reactions, making it a valuable building block for the development of new drugs and therapeutic agents.
Used in Medicinal Chemistry Research:
Due to its potential biological activity, 3-(4-Methoxybenzoyl)acrylic acid is used as a subject of interest in medicinal chemistry research. Scientists are exploring its properties and interactions with biological systems to understand its potential applications in the treatment of various diseases and conditions.
Used in Materials Science:
3-(4-Methoxybenzoyl)acrylic acid is used in the field of materials science, particularly in the development of functional polymers and coatings. Its chemical properties and reactivity make it suitable for the creation of advanced materials with specific properties, such as improved durability, resistance, or functionality.

InChI:InChI=1/C11H10O4/c1-15-9-4-2-8(3-5-9)10(12)6-7-11(13)14/h2-7H,1H3,(H,13,14)/b7-6+

Upstream product

• 24849-51-2 3-bromo-4-(4-methoxyphenyl)-4-oxobutanoic acid 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 127427-28-5 4-(4-methoxy-phenyl)-4-oxo-crotonic acid ethyl ester 
• 108-31-6 maleic anhydride 
• 100-66-3 methoxybenzene 
• 17615-10-0 methyl 4-(4-methoxyphenyl)-4-oxobut-2-enoate 
• 91142-97-1 4-(p-methoxyphenyl)-3-butenoic acid 
• 7553-56-2 iodine 
• 7647-01-0 hydrogenchloride 
• 5447-74-5 methyl 3-(4-methoxybenzoyl)propionate 
• 128934-96-3 2-hydroxy-4-(4-methoxyphenyl)but-3-enoic acid 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 1777-55-5 (4-methoxyphenacylidene)triphenyl phosphorane 

Downstream Products

• 101730-59-0 2-p-anisidino-4-(4-methoxy-phenyl)-4-oxo-butyric acid 
• 103862-60-8 2,3-dibromo-4-(4-methoxyphenyl)-4-oxobutanoic acid 
• 63639-60-1 2-hydroxy-4-(4-methoxy-phenyl)-4-oxo-butyric acid 
• 56428-35-4 3-(4-methoxybenzoyl)-2'.6'-dimethylacrylanilide 
• 67756-16-5 1-(4'-chlorophenyl)-4-(4''-methoxyphenyl)-butane-1,4-dione 
• 298-12-4 Glyoxilic acid 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 106422-25-7 3-(4-methoxy-phenyl)-5-oxo-cyclohex-3-enecarboxylic acid 
• 132590-32-0 5-Bromo-1-(4-methoxy-benzoyl)-benzo[f]chromen-3-one 
• 132590-30-8 1,2-Dibromo-1-(4-methoxy-benzoyl)-1,2-dihydro-benzo[f]chromen-3-one 
• 132590-26-2 1-(4-Methoxy-benzoyl)-2-[1-phenyl-meth-(Z)-ylidene]-1,2-dihydro-benzo[f]chromen-3-one 
• 132590-38-6 (4-Methoxy-phenyl)-[11-(4-methoxy-phenyl)-9-phenyl-8,12-dihydro-11H-7-oxa-8-aza-benzo[a]anthracen-12-yl]-methanone 
• 132590-40-0 2-Benzoyl-1,3-bis-(4-methoxy-phenyl)-3a,11c-dihydro-3H-5-oxa-cyclopenta[c]phenanthren-4-one 
• 132590-34-2 1-(4-Methoxy-benzoyl)-2-[1-(4-methoxy-phenyl)-3-oxo-3-phenyl-propyl]-1,2-dihydro-benzo[f]chromen-3-one 

Relevant academic research and scientific papers

Synthesis of chiral γ-lactones via a RuPHOX-Ru catalyzed asymmetric hydrogenation of aroylacrylic acids

An asymmetric hydrogenation of aroylacrylic acids catalyzed by RuPHOX-Ru catalyst has been developed, affording the corresponding chiral γ-lactones in high yields and with up to 93% ee. The methodology has the advantage of utilizing easily accessible substrates and has therefore expand the scope of the resulting chiral γ-lactones. Furthermore, high catalytic efficiency was achieved in that the reduction of both the C[dbnd]C and C[dbnd]O double bonds was achieved in one step. The current work provides an alternative and convenient pathway for the synthesis of a wide range of chiral γ-lactones.

Synthesis, antioxidant and antimicrobial activities of novel thiopyrano[2,3-d]thiazoles based on aroylacrylic acids

Abstract: Here it is described the synthesis, antioxidant and antimicrobial activity determination of novel rel-(5 R, 6 S, 7 R)-6-benzoyl-7-phenyl-2-oxo-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazole-5-carboxylic acids. The target compounds were obtained in good yields from 5-arylidene-4-thioxo-2-thiazolidinones and β -aroylacrylic acids via regio- and diastereoselective hetero-Diels–Alder reaction. The stereochemistry of the cycloaddition was confirmed by NMR spectra. The antioxidant and antimicrobial activity screening identified 7 compounds (3c, 3e, 3f, 3g, 3k, 3l, 3p) with a high level of free radical scavenging (43–77% DPPH assay), and compounds with significant influence on Staphylococcus aureus, Bacillus subtilis and Candida albicans (MIC 3.13–6.25 μ g/mL), but slight effect on Escherichia coli.

Synthesis and biological evaluations of 1,2-diaryl pyrroles as analogues of combretastatin A-4

A series of novel 1,2-diaryl pyrroles as analogues of combretastatin A-4 (CA-4, 1a) were synthesized and evaluated for their antitumour potential against three cancer cell lines. Most compounds exhibited growth inhibition against all of the cancer cell lines. Compound 7q not only exhibited prominent antitumour efficacy with IC50 values of 0.390 μm in SGC-7901, 0.070 μm in HT-1080 and 0.045 μm in KB cell lines but also showed low activity with IC50 values of 30.08 μm in normal L929 cell line. Moreover, compound 7q inhibited tubulin polymerization into microtubules and caused microtubule destabilization. A molecular docking study of 7q was performed to determine its binding mode at the colchicine site in the tubulin dimer. 1,2-Diaryl pyrroles as combretastatin A-4 analogues were synthesized and evaluated for anti-proliferative activities. Compound 7q exhibited antitubulin activity.

Structure-activity relationship, cytotoxicity and mode of action of 2-ester-substituted 1,5-benzothiazepines as potent antifungal agents

Our studies examined the structural features responsible for the antifungal activity of 2-ethoxycarbonyl-1,5-benzothiazepine (7a). Three series of 1,5-benzothiazepine derivatives were synthesized and screened for their antifungal activity. The results suggested that the ethoxycarbonyl group at the 2 position and the imine moiety on the seven-membered ring are essential for activity. The most potent of the synthesized analogues (7a, 7b) were further studied by evaluating their cytotoxicity and mode of action (for 7a). The results showed that compounds 7a and 7b were relatively safe for BV2 cells, but compound 7a interfered with Cryptococcus neoformans cell wall integrity by increasing the chitinase activity. Therefore, compound 7a was considered safe as an antifungal agent for animal cells. Three series of 1,5-benzothiazepine derivatives were synthesized and their antifungal activities were evaluated to determine the structure-activity relationships with respect to the antifungal activity of 2-ester-substituted 1,5-benzothiazepines. The effective antifungal compounds 7a and 7b were further studied for their antifungal activity, cytotoxicity and mechanism of action (for compound 7a). The results provided important information about this class of benzothiazepines. Copyright

Synthesis and evaluation of anticancer activity of some novel 6-aryl-2-(p-sulfamylphenyl)-pyridazin-3(2H)-ones

A series of novel pyridazinone derivatives bearing benzenesulfonamide moiety (2a-h) has been synthesized by the condensation of appropriate aroylacrylic acid and 4-hydrazinobenzenesulfonamide hydrochloride in ethanol. Five derivatives (2a, 2b, 2d, 2g and 2h) were evaluated for their anticancer activity toward human cancer cell lines by the National Cancer Institute. The 2h showed remarkable activity against SR (leukemia) and NCI-H522 (non-small cell lung) with a GI50 value of less than 0.1 μM. It also displayed good activity against leukemia (CCRF-CEM, HL-60 (TB), K-562, MOLT-4, RPMI-8226), non-small cell lung cancer (NCI-H460), colon (HCT-116, HCT-15, HT29, KMI2, SW-620), CNS (SF-295), melanoma (MALME-3M, M14, MDA-MB-435 SK-MEL-5), ovarian (OVCAR-3, NCI/ADR-RES) and breast (MCF7) cancer cell lines with a GI 50 less than 1.0 μM. The acute toxicity study of 2h indicated that it is well tolerated intra-peritoneally (400 mg/kg) by athymic nude mice. The 2h may possibly be used as lead compound for developing new anticancer agents.

4-Aryl-4-oxo-N-phenyl-2-aminylbutyramides as acetyl- and butyrylcholinesterase inhibitors. Preparation, anticholinesterase activity, docking study, and 3D structure-activity relationship based on molecular interaction fields

Synthesis and anticholinesterase activity of 4-aryl-4-oxo-N-phenyl-2-aminylbutyramides, novel class of reversible, moderately potent cholinesterase inhibitors, are reported. Simple substituent variation on aroyl moiety changes anti-AChE activity for two orders of magnitude; also substitution and type of hetero(ali)cycle in position 2 of butanoic moiety govern AChE/BChE selectivity. The most potent compounds showed mixed-type inhibition, indicating their binding to free enzyme and enzyme-substrate complex. Alignment-independent 3D QSAR study on reported compounds, and compounds having similar potencies obtained from the literature, confirmed that alkyl substitution on aroyl moiety of molecules is requisite for inhibition activity. The presence of hydrophobic moiety at close distance from hydrogen bond acceptor has favorable influence on inhibition potency. Docking studies show that compounds probably bind in the middle of the AChE active site gorge, but are buried deeper inside BChE active site gorge, as a consequence of larger BChE gorge void.

Syntheses of 1,5-Benzothiazepines: Part II - Synthesis of 4-Aryl-2-carboxy-2,3-dihydro-1,5-benzothiazepines

β-Aroylacrylic acids (II) react with 2-aminothiophenols (I) in ethanol containing gl.acetic acid to give 4-aryl-2-carboxy-2,3-dihydro-1,5-benzothiazepines (VII).Their structures have been established by elemental analyses and spectral data (IR, PMR, 13C NMR and mass).