18166-63-7

Usage

Uses

Used in Pharmaceutical Research and Development:
(2E)-3-(4-methoxyphenyl)prop-2-enamide is used as a research compound for exploring its potential therapeutic applications in the development of new drugs. Its unique structure and biological activities make it a promising candidate for further investigation in medicinal chemistry.
Used in Medicinal Chemistry:
(2E)-3-(4-methoxyphenyl)prop-2-enamide is used as a compound of interest in medicinal chemistry due to its potential role as an anti-inflammatory agent. Its distinctive structural features and biological properties contribute to its potential use in the discovery and design of new pharmaceutical agents targeting inflammation-related diseases.
Used in Scientific Research:
(2E)-3-(4-methoxyphenyl)prop-2-enamide is utilized in various scientific fields for studying its chemical properties, reactivity, and potential interactions with other molecules. This research can provide valuable insights into the compound's behavior and its possible applications in different areas of science.

Upstream product

• 696-62-8 para-iodoanisole 
• 79-06-1 2-propenamide 
• 619-44-3 methyl 4-iodobenzoate 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 706783-20-2 C₁₀H₁₃NO₂⁽²⁺⁾ 
• 123-11-5 4-methoxy-benzaldehyde 
• 75-05-8 acetonitrile 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 24680-50-0 4-methoxy-trans-cinnamaldehyde 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 42996-84-9 p-methoxycinnamoyl chloride 
• 18166-58-0 α-Chlor-β-(p-methoxy-phenyl)-propionsaeureamid 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 118653-08-0 [(E)-2-(4-Methoxy-phenyl)-vinyl]-carbamic acid methyl ester 
• 25413-27-8 3-(4-methoxy-phenyl)propionamide 
• 1194827-03-6 (Z)-3-(4-methoxyphenyl)acrylamide 
• 70126-13-5 (4-methoxy-styryl)-carbamic acid methyl ester 
• 22101-03-7 3-(4-methoxyphenyl)-3-phenylpropionamide 
• 706783-20-2 C₁₀H₁₃NO₂⁽²⁺⁾ 
• 195616-19-4 (2R,3S)-3-(4-methoxyphenyl)glycidic amide 
• 47230-38-6 diethyl biphenyl-4,4'-dicarboxylate 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 767329-19-1 4-chloromethyl-2-[2-(4-methoxy-phenyl)-vinyl]-oxazole 

Relevant academic research and scientific papers

Identification of a novel toxicophore in anti-cancer chemotherapeutics that targets mitochondrial respiratory complex i

Disruption of mitochondrial function selectively targets tumour cells that are dependent on oxidative phosphorylation. However, due to their high energy demands, cardiac cells are disproportionately targeted by mitochondrial toxins resulting in a loss of cardiac function. An analysis of the effects of mubritinib on cardiac cells showed that this drug did not inhibit HER2 as reported, but directly inhibits mitochondrial respiratory complex I, reducing cardiac-cell beat rate, with prolonged exposure resulting in cell death. We used a library of chemical variants of mubritinib and showed that modifying the 1H-1,2,3-triazole altered complex I inhibition, identifying the heterocyclic 1,3-nitrogen motif as the toxicophore. The same toxicophore is present in a second anti-cancer therapeutic carboxyamidotriazole (CAI) and we demonstrate that CAI also functions through complex I inhibition, mediated by the toxicophore. Complex I inhibition is directly linked to anti-cancer cell activity, with toxicophore modification ablating the desired effects of these compounds on cancer cell proliferation and apoptosis.

Mizoroki–Heck Cross-Coupling of Acrylate Derivatives with Aryl Halides Catalyzed by Palladate Pre-Catalysts

The Mizoroki–Heck (MH) reaction involving aryl halides with various acrylates and acrylamides has been studied using air and moisture-stable imidazolium-based palladate pre-catalysts. These pre-catalysts can be converted into Pd-NHC species (NHC = N-heterocyclic carbene) under catalytic conditions and are capable of facilitating the Mizoroki–Heck reaction of aryl halides with various acrylates. The effects of solvent, catalyst loading, temperature and bases on the reaction outcome have been investigated. Various coupling partners were tolerated under the optimal reaction conditions catalyzed by palladate 1, [SIPr·H][Pd(η3-2-Me-allyl)Cl2]. The efficiency of the optimized synthetic methodology was tested on various aryl halides and substituted acrylates as well as acrylamides. The MH reaction yielded the coupled products in good to excellent isolated yields (up to 98%).

Direct and facile synthesis of primary amides from carboxylic acids via acyl isocyanate intermediates using mukaiyama reagent

A very simple and efficient procedure for the preparation of primary amides is described from carboxylic acids using Mukaiyama reagent/KNCO in aqueous acetonitrile. Availability of the reagents, simplicity, and easy workup of the reaction crude make this method attractive for organic chemists.

Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source

The direct conversion of α,β-unsaturated aldehydes to corresponding nitriles promoted by Pd(OAc)2 and phthalic acid which was hydrolyzed from N-hydroxyphthalimide (NHPI) has been disclosed. Additionally, it was found that when water was used as the solvent, α,β-unsaturated amides was obtained as the main products in good to excellent yields. It was first reported that NHPI was utilized as the nitrogen source to synthesize α,β-unsaturated nitriles and amides from aldehydes. Control experiment demonstrated that aldehydes undergo a process of oximation and dehydration to form nitriles and amides.

Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides to Form Nitriles

A palladium(II) catalyst, in the presence of Selectfluor, enables the efficient and chemoselective transformation of primary amides into nitriles. The amides can be attached to aromatic rings, heteroaromatic rings, or aliphatic side chains, and the reactions tolerate steric bulk and electronic modification. Dehydration of a peptaibol containing three glutamine groups afforded structure-activity relationships for each glutamine residue. Thus, this dehydration can act similarly to an alanine scan for glutamines via synthetic mutation.

Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1S,2R)-tranylcypromine

Primary amidations of carboxylic acids 1 or 3 with NH4Cl in the presence of ClCO2Et and Et3N were developed to afford the corresponding primary amides in 22% to quantitative yields. Additionally, we have applied the amidation to the preparation of various amides containing hydroxamic acids and achieved the synthesis of (1S,2R)-tranylcypromine as an antidepressant medicine via Lossen rearrangement.

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.

Optimization and Evaluation of 5-Styryl-Oxathiazol-2-one Mycobacterium tuberculosis Proteasome Inhibitors as Potential Antitubercular Agents

This is the first report of 5-styryl-oxathiazol-2-ones as inhibitors of the Mycobacterium tuberculosis (Mtb) proteasome. As part of the study, the structure-activity relationship of oxathiazolones as Mtb proteasome inhibitors has been investigated. Furthermore, the prepared compounds displayed a good selectivity profile for Mtb compared to the human proteasome. The 5-styryl-oxathiazol-2-one inhibitors identified showed little activity against replicating Mtb, but were rapidly bactericidal against nonreplicating bacteria. (E)-5-(4-Chlorostyryl)-1,3,4-oxathiazol-2-one) was most effective, reducing the colony-forming units (CFU)/mL below the detection limit in only seven days at all concentrations tested. The results suggest that this new class of Mtb proteasome inhibitors has the potential to be further developed into novel antitubercular agents for synergistic combination therapies with existing drugs.

METHOD FOR PRODUCING 4-METHOXY CINNAMIC ACID 2-ETHYLHEXYL COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing a 4-methoxy cinnamic acid 2-ethylhexyl compound friendly for the environment under mild conditions using an inexpensive reagent. SOLUTION: A 4-methoxy cinnamic acid 2-ethylhexyl compound is obtained through: a first step in which a 4-hydroxy cinnamic acid amide compound is treated with a methylation agent to obtain a 4-methoxy cinnamic acid amide compound; a second step in which the 4-methoxy cinnamic acid amide compound is hydrolyzed with acid or a base to obtain a 4-methoxy cinnamic acid compound; and a third step in which the 4-methoxy cinnamic acid compound and the 2-ethyl-1-hexanol are condensed to form an ester linkage. COPYRIGHT: (C)2015,JPOandINPIT

Heck arylation of conjugated alkenes with aryl bromides or chlorides catalyzed by immobilization of palladium in MCM-41

A new 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized palladium(II) complex [MCM-41-2N-PdCl2] was conveniently synthesized from commercially available and cheap 3-(2-aminoethylamino) propyltrimethoxysilane via immobilization on MCM-41, followed by reacting with palladium chloride. It was found that this heterogeneous palladium complex is a highly efficient catalyst for Heck arylation of conjugated alkenes with aryl bromides or chlorides using tetrabutylammonium bromide as additive and can be reused for at least six consecutive trials without any decreases in activity.