13565-06-5

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-3-(3-chlorophenyl)acryloyl chloride is used as a synthetic intermediate for the preparation of various pharmaceuticals. Its reactivity allows for the creation of new drug candidates by forming amides and esters with amines and alcohols, respectively.
Used in Agrochemical Industry:
In the agrochemical sector, (2E)-3-(3-chlorophenyl)acryloyl chloride serves as a key component in the synthesis of pesticides and other agrochemicals. Its ability to react with nucleophiles facilitates the development of new compounds with potential applications in crop protection and enhancement.
Used in Coatings and Adhesives Industry:
(2E)-3-(3-chlorophenyl)acryloyl chloride is used as a building block in the preparation of polymers and materials for coatings and adhesives. Its incorporation into these materials can enhance their properties, such as adhesion, durability, and resistance to environmental factors.
Used in Fine Chemicals Industry:
(2E)-3-(3-chlorophenyl)acryloyl chloride is also utilized in the synthesis of fine chemicals, which are high-purity, specialty chemicals used in various applications, including research, pharmaceuticals, and other industries. Its versatility in forming different chemical bonds makes it a valuable asset in this field.
Overall, (2E)-3-(3-chlorophenyl)acryloyl chloride is a versatile compound with various synthetic and industrial applications, particularly in the development of pharmaceuticals, agrochemicals, coatings, adhesives, and fine chemicals.

Upstream product

• 770-23-0 (E)-3-(3-chlorophenyl)propenal 
• 79-37-8 oxalyl dichloride 
• 1866-38-2 m-Chlorocinnamic acid 
• 1866-38-2 3-chlorocinnamic acid 
• 587-04-2 m-Chlorobenzaldehyde 

Downstream Products

• 1080637-18-8 methyl 5-hydroxy-7-(3-chlorophenyl)-3-oxohepta-4,6-dienoate 
• 2373-88-8 3-(3-chloro-phenyl)-acrylic acid ethyl ester 
• 104724-21-2 (E)-3-(3-Chloro-phenyl)-N-[2-(5-methoxy-1H-indol-3-yl)-ethyl]-acrylamide 
• 221650-78-8 S-methyl (E)-3-(3-chlorophenyl)prop-2-enethioate 
• 882788-18-3 N-(2-allyl-3,5-dimethyl-phenyl)-3-(3-chloro-phenyl)-acrylamide 
• 100098-79-1 2-[(E)-2-(3-Chloro-phenyl)-vinyl]-4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazine; hydrochloride 
• 22966-13-8 (2E)-3-(3-chlorophenyl)-1-phenylprop-2-en-1-one 
• 13565-42-9 3-(3-chlorophenyl)-1-(4-methylphenyl)-(2E)-2-propen-1-one 
• 1047680-79-4 3-(3-chlorophenyl)-1-(4-methoxyphenyl)-(2E)-2-propen-1-one 
• 1290048-18-8 3-{(R)-4-[(E)-3-(3-chloro-phenyl)-acryloyl]-3-methyl-7-oxo-[1,4]diazepan-1-yl}-propionic acid 
• 1290048-22-4 (R)-1-[(E)-3-(3-Chloro-phenyl)-acryloyl]-4-(3-hydroxy-propyl)-2-methyl-[1,4]diazepan-5-one 

Relevant academic research and scientific papers

Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives

This work deals with the design and synthesis of 18 barbituric acid derivatives bearing 1,3-dimethylbarbituric acid and cinnamic acid scaffolds to find potent anticancer agents. The target molecules were obtained through Knoevenagel condensation and acylation reaction. The cytotoxicity was assessed by the MTT assay. Flowcytometry was performed to determine the cell cycle arrest, apoptosis, ROS levels and the loss of MMP. The ratios of GSH/GSSG and the MDA levels were determined by using UV spectrophotometry. The results revealed that introducing substitutions (CF3, OCF3, F) on the meta- of the benzyl ring of barbituric acid derivatives led to a considerable increase in the antiproliferative activities compared with that of corresponding ortho- and para-substituted barbituric acid derivatives. Mechanism investigation implied that the 1c could increase the ROS and MDA level, decrease the ratio of GSH/GSSG and MMP, and lead to cell cycle arrest. Further research is needed for structural optimization to enhance hydrophilicity, thereby improve the biological activity of these compounds.

Stereocontrolled Synthesis of trans/ cis-2,3-Disubstituted Cyclopropane-1,1-diesters and Applications in the Syntheses of Furanolignans

A new Michael addition/intramolecular alkylation sequence of (Z)-3-(2-bromo-3-arylacryloyl)oxazolidin-2-ones and malonates was developed. By a simple switch of the reaction conditions including the base promoter, solvent, and reaction temperature, both of the cis- and trans-isomers of a series of oxazolidinone-containing 2,3-disubstituted cyclopropane-1,1-diesters could be obtained in good-to-excellent yields and with an excellent diastereoselectivity. The utility of the cyclopropane products was demonstrated in the diastereoselective syntheses of (±)-urinaligran and a stereoisomer of (±)-virgatusin involving the AlCl3-promoted [3+2] annulation with veraldehyde or piperonal as the key step.

Bioactivity and structure-activity relationship of cinnamic acid esters and their derivatives as potential antifungal agents for plant protection

A series of cinnamic acid esters and their derivatives were synthesized and evaluated for antifungal activities in vitro against four plant pathogenic fungi by using the mycelium growth rate method. Structure-activity relationship was derived also. Almost all of the compounds showed some inhibition activity on each of the fungi at 0.5 mM. Eight compounds showed the higher average activity with average EC50 values of 17.4-28.6 μg/mL for the fungi than kresoxim-methyl, a commercial fungicide standard, and ten compounds were much more active than commercial fungicide standards carbendazim against P. grisea or kresoxim-methyl against both P. grisea and Valsa Mali. Compounds C1 and C2 showed the higher activity with average EC50 values of 17.4 and 18.5 μg/mL and great potential for development of new plant antifungal agents. The structure-activity relationship analysis showed that both the substitution pattern of the phenyl ring and the alkyl group in the alcohol moiety significantly influences the activity. There exists complexly comprehensive effect between the substituents on the phenyl ring and the alkyl group in the alcohol moiety on the activity. Thus, cinnamic acid esters showed great potential the development of new antifungal agents for plant protection due to high activity, natural compounds or natural compound framework, simple structure, easy preparation, low-cost and environmentally friendly.

Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N4 Ligands Derived from Rigid Chiral Diamines

A series of tetradentate sp2N/sp3N hybrid chiral N4 ligands derived from rigid chiral diamines were synthesized, which enabled the first manganese-catalyzed enantioselective epoxidation of electron-deficient alkenes with hydrogen peroxide (H2O2) as an oxidant. The reaction furnishes enantiomerically pure epoxy amides, epoxy ketones as well as epoxy esters in good yields and excellent enantioselectivities (up to 99.9% ee) with lower catalyst loading. Preliminary studies on structure–activity relationship demonstrated that maintaining comparatively lower electron-donating ability of the sp3N and relatively higher electron-donating ability of sp2N of the N4 ligands is beneficial to getting higher activity and selectivity, thus providing us a new view to understand epoxidation with H2O2. (Figure presented.).

Design, synthesis and cytotoxic evaluation of novel imatinib amide derivatives that target Abl kinase

Novel imatinib amide derivatives (a1-28, b1-9) were synthesized and evaluated for their biological activities. All compounds were characterized by 1H NMR, MS and elemental analysis. Among all the derivatives, compounds a4, a10, a21, b1 and b2 displayed the most significant ability of inhibiting K562 cell proliferation with the IC50 values of 0.67, 0.66, 0.65, 0.59 and 0.62 μM, respectively, indicating that these compounds were potent inhibitors of Bcr-Abl in leukemic K562 cells, comparable to the reference compound imatinib. Molecular docking study was performed to position compounds a21 and b1 into the active site of Abl to determine the probable binding modes

Synthesis and anti-influenza activities of novel baicalein analogs

A series of novel flavones derivatives were synthesized based on modification of the active ingredients of a traditional Chinese medicine Scutellaria baicalensis GEORGI and screened for anti-influenza activity. The synthetic baicalein (flavone) analogs, especially with the B-rings substituted with bromine atoms, were much more potent than oseltamivir or ribavirin against H1N1 Tamiflu-resistant (H1N1 TR) virus and usually with more favorable selectivity. The most promising were 5b, 5c, 6b and 6c, all displaying an 50% effective concentration (EC50) at around 4.0-4.5 μM, and a selective index (SI=50% cytotoxic concentration (CC50)/EC 50)>70. For seasonal H3N2-infected influenza virus, both 5a and 5b with SI >17.3 indicated superior to ribavirin. The flavonoids having both not-naturally-occurring bromo-substituted B-rings and appropriate hydroxyls positioning on the A-rings might be critical in determining the activity and selectivity against H1N1-Tamiflu-resistant infected influenza viruses.

The triflic acid-mediated cyclisation of N-benzyl-cinnamamides

N-Benzyl-cinnamamides cyclise with triflic acid to form 5-aryl-benzazepinones and/or cinnamamides.

The triflic acid-mediated cyclisation of N-benzylcinnamanilides

N-Benzylcinnamanilides cyclise with triflic acid to form 1-benzyl-4-aryl-2,4-dihydro-1H-quinolin-2-ones and 2,5-diaryl-benzazepin-3-ones. The product ratio is determined by the preferred orientation of the amide and by the electronics of the substituents. With ortho-substituted anilides, N-debenzylation also occurs to give 4-aryl-2,4-dihydro-1H-quinoline-2-ones.

Syntheses and structure-activity relationship studies of N-substituted-β-d-glucosaminides as selective cytotoxic agents

Twenty-four diosgenyl saponins bearing cinnamoyl, carbamido and thiosemicarbazone groups were synthesized concisely. The cytotoxicities of the synthetic compounds on six human caner cell lines were evaluated employing MTT method. Structure-activity relationship could be observed, and two of the synthesized compounds (5c and 5f) exhibited selective inhibition on HeLa and MCF-7 cells, while three of them (5d, 5f and 5h) showed strong inhibition against HT1080.

Synthesis, antiproliferative activity, and mechanism of action of a series of 2-{[(2E)-3-phenylprop-2-enoyl]amino}benzamides

Several new 2-{[(2E)-3-phenylprop-2-enoyl]amino}benzamides 12a-s and 17t-v were synthesized by stirring in pyridine the (E)-3-(2-R1-3-R2-4-R3-phenyl) acrylic acid chlorides 11c-k and 11t-v with the appropriate anthranilamide derivatives 10a-c or the 5-iodoanthranilic acid 13. Some of the synthesized compounds were evaluated for their in vitro antiproliferative activity against the full NCI tumor cell line panel derived from nine clinically isolated cancer types (leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate and breast). COMPARE analysis, effects on tubulin polymerization in cells and with purified tubulin, and effects on cell cycle distribution for 17t, the most active of the series, indicate that these new antiproliferative compounds act as antitubulin agents.