88681-63-4

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
(Z)-2-ACETAMIDO-3-(4-CHLOROPHENYL)ACRYLIC ACID is used as a pharmaceutical compound for its potential anti-inflammatory and analgesic properties. It serves as a promising candidate for the development of new drugs targeting inflammation and pain management.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (Z)-2-ACETAMIDO-3-(4-CHLOROPHENYL)ACRYLIC ACID is used as a building block for the synthesis of various organic compounds. Its unique structure allows for the creation of diverse molecules with potential therapeutic applications.
Used in Synthetic Chemistry:
(Z)-2-ACETAMIDO-3-(4-CHLOROPHENYL)ACRYLIC ACID is also utilized in synthetic chemistry as a valuable chemical for the development of new materials and compounds with specific properties and functions. Its amide and chlorophenyl groups provide a foundation for further chemical modifications and innovations.

Upstream product

• 93634-55-0 2-methyl-4-(4-chlorobenzylidene)-4H-oxazol-5-one 
• 106-39-8 bromochlorobenzene 
• 5429-56-1 N-Acetamidoacrylic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 543-24-8 N-acetylglycine 
• 93634-55-0 (Z)-4-(4-chlorobenzylidene)-2-methyloxazol-5(4H)-one 

Downstream Products

• 14091-10-2 (S)-2-acetamido-3-(4-chlorophenyl)propanoic acid 
• 1601468-79-4 3-(4-chlorophenyl)-2-(2-(4-(3,4-dichlorophenyl)thiazol-2-yl)hydrazono)propanoic acid 
• 1601468-78-3 3-(4-chlorophenyl)-2-(2-(4-(3,4-dichlorophenyl)thiazol-2-yl)hydrazono)propanoic acid 
• 127273-12-5 3-(4-chlorophenyl)-2-hydroxyacrylic acid 
• 3617-01-4 β-(4-chlorophenyl)pyruvic acid 
• 102245-02-3 methyl (Z)-2-acetylamino-3-(4-chlorophenyl)-2-propenoate 
• 14091-10-2 N-acetyl-4-chlorophenylalanine 
• 33401-57-9 6-(4-chlorobenzyl)-3-thioxo-3,4-dihydro-[1,2,4]-triazin-5(2H)-one 
• 202651-01-2 4-{[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-amino}-6-(4-chloro-benzyl)-3-mercapto-4H-[1,2,4]triazin-5-one 
• 202651-06-7 6-Benzo[1,3]dioxol-5-ylmethyl-3-mercapto-4-{[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-4H-[1,2,4]triazin-5-one 
• 202651-00-1 6-(4-Chloro-benzyl)-3-mercapto-4-{[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-4H-[1,2,4]triazin-5-one 
• 202650-99-5 6-(4-Chloro-benzyl)-3-mercapto-4-{[1-p-tolyl-meth-(E)-ylidene]-amino}-4H-[1,2,4]triazin-5-one 
• 22278-75-7 6-(p-chlorobenzyl)-4-amino-3-mercapto-1,2,4-triazin-5-one 

Relevant academic research and scientific papers

Synthesis, biological activity, molecular docking studies of a novel series of 3-Aryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives as the acetylcholinesterase inhibitors

The acetylcholinesterase inhibitors play a critical role in the drug therapy for Alzheimer’s disease. In this study, twenty-nine novel 3-aryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were synthesized and assayed for their human acetylcholinesterase (hAChE) inhibitory activities. Inhibitory ratio values of seventeen compounds were above 55% with 4c having the highest value as 77.19%. The compounds with the halogen atoms in the aromatic ring, and N,N-diethylamino or N,N-dimethylamino groups in the side chains at C-3 positions exhibited good inhibitory activity. SAR study was carried out by means of molecular docking technique. According to molecular docking results, the common interacting site for all compounds were found to be peripheral anionic site whereas highly active compounds were interacting with the catalytic active site too. HIGHLIGHTS A novel series of 3-aryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were synthesized and assayed for their human acetylcholinesterase (hAChE) inhibitory activities. The SAR study of the target 3-aryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives was summarized. The active sites in the acetylcholinesterase were analyzed by molecular docking technique. Communicated by Ramaswamy H. Sarma.

Synthesis, β-catenin translocation capability and ALP activation activity of 7h-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives

Background: Osteoporosis (OP) is a common bone disease, most often diagnosed in post-menopausal women. The majority of OP treatments are focused on manipulation of the patient's hormone levels, therefore, they are associated with significant adverse effects. Objective: The study aimed to design, synthesize and evaluate the β-Catenin translocation capability and the alkaline phosphatase (ALP) activation activity of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives. Method: The styrene derivatives were synthesized as raw materials, followed by oxidation and condensation reactions, in which 6-aryl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one derivatives (1) were obtained. The 3,6-diaryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-ones (2) were obtained by a condensation reaction of compound 1 with substituted phenacyl chlorides in acetic acid. The target compounds 3,6-diaryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-ones (3a-3c) were prepared by compound 2 with substituted alkyl chloride by Williamson reaction. As to 6-benzyl-3-aryl-7H-thiazolo[3,2- b]-1,2,4-triazin-7-one derivatives as the target compounds, the benzaldehyde and acetylglycine used as raw materials, followed by Erlenmeyer-Pl?chl reaction, condensation reaction, hydrolysis reaction, condensation reaction, 6-benzyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one derivatives were obtained, and were converted to the target compounds 6-benzyl-3-(hydroxylaryl)-7Hthiazolo[ 3,2-b]-1,2,4-triazin-7-one derivatives (5a-5d) using reaction with substituted β-phenacyl chlorides. Finally, Williamson reaction were used to yield 6-benzyl-3-aryl-7H-thiazolo[3,2-b]- 1,2,4-triazin-7-ones as target compounds (6a-6e). The β-Catenin translocation capability and the ALP activation activity were tested, and the glycogen synthase kinase-3 (GSK-3) inhibition was simulated by molecular docking. Results: Fourteen 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were synthesized and characterized by mass spectra, proton NMR and infrared spectra, the β-Catenin translocation capability and the ALP activation activities of the target compounds were tested and calculated. The EC50 value of the ALP activation activity of 6-(4-chlorobenzyl)-3-{4-[(2-dimethylamino)-2- oxoethoxy]phenyl}-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one (6b) was 11.283 μM. The molecular docking results have showed that the target compounds would be GSK-3 inhibitors. Conclusion: Based on the results of the biological activity test, the target compounds have exhibited the β-Catenin translocation capability and the ALP activation activity.

Systematic methodology for the development of biocatalytic hydrogen-borrowing cascades: Application to the synthesis of chiral α-substituted carboxylic acids from α-substituted α,β-unsaturated aldehydes

Ene-reductases (ERs) are flavin dependent enzymes that catalyze the asymmetric reduction of activated carbon-carbon double bonds. In particular, α,β-unsaturated carbonyl compounds (e.g. enals and enones) as well as nitroalkenes are rapidly reduced. Conversely, α,β-unsaturated esters are poorly accepted substrates whereas free carboxylic acids are not converted at all. The only exceptions are α,β-unsaturated diacids, diesters as well as esters bearing an electron-withdrawing group in α- or β-position. Here, we present an alternative approach that has a general applicability for directly obtaining diverse chiral α-substituted carboxylic acids. This approach combines two enzyme classes, namely ERs and aldehyde dehydrogenases (Ald-DHs), in a concurrent reductive-oxidative biocatalytic cascade. This strategy has several advantages as the starting material is an α-substituted α,β-unsaturated aldehyde, a class of compounds extremely reactive for the reduction of the alkene moiety. Furthermore no external hydride source from a sacrificial substrate (e.g. glucose, formate) is required since the hydride for the first reductive step is liberated in the second oxidative step. Such a process is defined as a hydrogen-borrowing cascade. This methodology has wide applicability as it was successfully applied to the synthesis of chiral substituted hydrocinnamic acids, aliphatic acids, heterocycles and even acetylated amino acids with elevated yield, chemo- and stereo-selectivity. A systematic methodology for optimizing the hydrogen-borrowing two-enzyme synthesis of α-chiral substituted carboxylic acids was developed. This systematic methodology has general applicability for the development of diverse hydrogen-borrowing processes that possess the highest atom efficiency and the lowest environmental impact. This journal is

Structure-activity relationship study of 4EGI-1, small molecule eIF4E/eIF4G protein-protein interaction inhibitors

Abstract Protein-protein interactions are critical for regulating the activity of translation initiation factors and multitude of other cellular process, and form the largest block of untapped albeit most challenging targets for drug development. 4EGI-1, (E/Z)-2-(2-(4-(3,4-dichlorophenyl)thiazol-2-yl) hydrazono)-3-(2-nitrophenyl)propanoic acid, is a hit compound discovered in a screening campaign of small molecule libraries as an inhibitor of translation initiation factors eIF4E and eIF4G protein-protein interaction; it inhibits translation initiation in vitro and in vivo. A series of 4EGI-1-derived thiazol-2-yl hydrazones have been designed and synthesized in order to delineate the structural latitude and improve its binding affinity to eIF4E, and increase its potency in inhibiting the eIF4E/eIF4G interaction. Probing a wide range of substituents on both phenyl rings comprising the 3-phenylpropionic acid and 4-phenylthiazolidine moieties in the context of both E- and Z-isomers of 4EGI-1 led to analogs with enhanced binding affinity and translation initiation inhibitory activities.

Asymmetric synthesis of unnatural amino acids and tamsulosin chiral intermediate

An efficient and enantioselective hydrogenation of N-acetylamino phenyl acrylic acids was successfully developed by using ruthenium catalyst. This methodology is important in the field of pharmaceuticals and provides a new process for the preparation of unnatural amino acids and tamsulosin chiral intermediate.

Design, synthesis, and biological evaluation of 7H-thiazolo[3,2-b]-1,2,4- triazin-7-one derivatives as dual binding site acetylcholinesterase inhibitors

A series of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were designed, synthesized and evaluated as dual binding site acetylcholinesterase inhibitors. The target compounds exhibited promising inhibitory activity for AChE. The structure-activity relationships were discussed and their binding conformation and simultaneous interactions mode were further clarified by the molecular docking studies.

Synthesis of oxazoles from enamides via phenyliodine diacetate-mediated intramolecular oxidative cyclization

A group of functionalized oxazoles were synthesized in moderate to good yields from enamides via phenyliodine diacetate (PIDA)-mediated intramolecular cyclization. The main advantageous features of the present method include its broad substrate scope and the heavy-metal-free characteristic of the oxidative carbon-oxygen bond formation process.

SUBSTITUTED BETA-PHENYL-ALPHA-HYDROXY PROPANOIC ACID, SYNTHESIS METHOD AND USE THEREOF

The present invention relates to a compound of the formula (I), wherein R1, R2 and R3 are each independently selected from H, OH, F, Cl, Br, methoxy and ethoxy; or alternatively, R1 and R2 together form -OCH2O-, R3 is selected from H, OH, methoxy, ethoxy and halogens; R4 is OH or acyloxy; R5 is cycloalkoxyl, amino and substituted amino, and when R5 is selected from amino, at least one of R1, R2 and R3 is not H. The present invention further relates to a process for synthesizing a compound of the formula (I), and use of the compound of the formula (I) in the manufacture of a medicament for the prevention or treatment of cardiovascular or cerebrovascular diseases.

Studies on arylmethyltriazinone derivatives-Part II. Synthesis and antifungal properties of 2-aminomethyl-4-(arylidene)amino-6-arylmethyl-3-mercapto-1, 2,4-triazin-5(4H)-ones

The preparation of twenty new 2-aminomethyl-4-(arylidene)amino-6-arylmethyl-3-mercapto-1,2,4-triazin-5(4H)- ones(4) is described. The structural elucidation of all the compounds is carried out on the basis of analytical and spectral data. The newly synthesized compounds are evaluated for their antifungal activity against Candida albicans and Paecileomyces variotti.