6269-33-6

Usage

Uses

Used in Organic Synthesis:
3-(4-CHLOROBENZOYL)ACRYLIC ACID is used as a building block in organic synthesis for its potential to create various functionalized molecules. Its unique structure allows for the development of new compounds with specific properties, making it a versatile component in chemical research and development.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-(4-CHLOROBENZOYL)ACRYLIC ACID is utilized as a key intermediate in the synthesis of biologically active compounds. Its presence in the molecular structure can influence the pharmacological properties of the final product, contributing to the discovery of new drugs and therapeutic agents.
Used as a Crosslinking Agent in Polymer and Resin Production:
3-(4-CHLOROBENZOYL)ACRYLIC ACID is employed as a crosslinking agent in the manufacturing of polymers and resins. Its reactivity, enhanced by the chlorine atom, facilitates the formation of strong bonds between polymer chains, resulting in materials with improved mechanical properties and stability.

InChI:InChI=1/C10H7ClO3/c11-8-3-1-7(2-4-8)9(12)5-6-10(13)14/h1-6H,(H,13,14)/b6-5+

Upstream product

• 89781-40-8 C₁₂H₁₁ClO₃ 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 99-91-2 para-chloroacetophenone 
• 298-12-4 Glyoxilic acid 
• 1777-56-6 4-chlorobenzoylmethylenetriphenylphosphorane 
• 2689-81-8 (4-chlorophenacyl)triphenylphosphonium bromide 
• 108-31-6 maleic anhydride 
• 108-90-7 chlorobenzene 

Downstream Products

• 7309-23-1 3-benzyl-5-[2-(4-chlorophenyl)-2-oxoethyl]-4-oxo-2-thioxo-1,3-thiazolidine 
• 21813-63-8 4-(4-Chlorphenyl)-2-morpholino-4-oxo-butansaeure 
• 24314-35-0 1,4-bis(4-chlorophenyl)butane-1,4-dione 
• 116274-72-7 4-(4-Chloro-phenyl)-2,3-dihydro-benzo[b][1,4]thiazepine-2-carboxylic acid 
• 147674-75-7 4-(4-Chloro-phenyl)-4-oxo-2-(5-oxo-1,3-diphenyl-4,5-dihydro-1H-pyrazol-4-yl)-butyric acid 
• 7350-45-0 5-<2-(4-chlorophenyl)-2-oxoethyl>-2-thioxo-4-oxo-1,3-thiazolidine 
• 170645-19-9 5-<2-(4-chlorophenyl)-2-oxoethyl>-3-(4-methylphenyl)-2-thioxo-4-oxo-1,3-thiazolidine 
• 924283-91-0 4-(4-chlorophenyl)-4-oxo-2-(4,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-yl)butyric acid 
• 924283-92-1 4-(4-chlorophenyl)-4-oxo-2-(2-oxocyclohexyl)butyric acid 
• 924283-88-5 2-acetyl-3-[2-(4-chlorophenyl)-2-oxoethyl]succinic acid 1-ethyl ester 
• 57192-22-0 2-[2-(4-chlorophenyl)-2-oxoethyl]-3-phenylsuccinic acid 4-ethyl ester 
• 924283-90-9 2-[2-(4-chlorophenyl)-2-oxoethyl]-3-cyanosuccinic acid 4-ethyl ester 
• 924283-89-6 3-acetyl-2-[2-(4-chlorophenyl)-2-oxoethyl]-4-oxopentanoic acid 
• 75371-29-8 6-acetyl-3-p-chlorophenyl-5-oxo-3-cyclohexene-1-carboxylic acid 

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.

A sertraline hydrochloride impurity preparation method (by machine translation)

The invention discloses a sertraline hydrochloride preparation method of impurities, in particular comprising a formula 6 by the Leuckart reaction to obtain a compound of the formula 7 compound, with the insulated hydrochloride salt obtained in the reaction formula 8 cis-isomer of the compound, wherein the formula 6 compound in the location of the chloropropyl substituted cyclohexanone substituted meta or para position. Preparation method of this invention is simple, high purity, obtained impurity can be used for qualitative and quantitative analysis, so as to improve the safety of medicine sertraline hydrochloride. (by machine translation)

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 applications of pyridazinones for base oil improvement

THREE pyridazinone derivatives of the type 4,5-dihydropyridazin- 3(2H)-ones, N-(4-(6-oxo-5- ((5-phenyl-1,3,4-thiadiazol-2-yl)amino) - 1,4,5,6 - tetrahydropyridazin - 3-yl) phenyl) acetamide (4a), 6-(4-chlorophenyl)-4-((5-phenyl-1,3,4-thiadiazol-2-yl)amino)-4,5-di-hydropyridazin-3 (2H)-one (4b) and 6-(4-bromophenyl) -4- ((5-phenyl-1,3,4-thiadiazol-2-yl) amino)-4,5-dihydropyridazin-3(2H)-one (4c) were synthesized. They were characterized by the conventional tools of analysis, Elemental analysis, IR and 1H-NMR spectroscopy. The tools of analysis confirmed the structure of the three prepared compounds. These heterocyclic compounds are chemically stable and possess multi actions for base oil improvement. They are tested as antioxidants for local base oil through the change in total acid number (TAN). They gave good results as antioxidants for base oil. Also these three synthesized compounds are tested as corrosion inhibitors for carbon steel in acid medium. The efficiency order for these tested compounds is ranked as follows: 4a > 4b > 4c. Energy of the highest occupied molecular orbital (EHOMO) and lowest unoccupied molecular orbital (ELUMO) for the three prepared compounds were calculated via the Ab initio method. Studying of the quantum chemical calculations of the synthesized compounds showed good matching with the experimental results.

Synthesis of 1,5-benzodiazepine derivatives using p-toluenesulfonic acid as catalyst

A series of substituted ethyl 4-oxo-4-phenylbut-2-enoates were prepared and reacted with substituted o-phenylenediamine, undergone Michael addition reactions and cyclodehydration to provide novel 4-phenyl-2,3-dihydro-1,5-benzodiazepine-2-carboxylate derivatives with excellent yields. The synthetic protocol fulfilled many green-chemical requirements by using simple catalyst p-toluenesulfonic acid as activator and ethanol as solvent at room temperature.

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.

Utility of β-(4-chlorobenzoyl)acrylic acid in heterocyclic synthesis

β-(4-Chlorobenzoyl)acrylic acid (1) proved to be a convenient precursor for the synthesis of a variety of heterocyclic systems through the reaction with compounds containing active methylene groups under Michael reaction conditions. Also, the reactivity o