51838-02-9

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
2-cyano-N-phenethyl-acetamide is used as a precursor for the synthesis of bioactive molecules, which are essential in the development of various pharmaceutical products. Its role in creating antifungal, antibacterial, analgesic, anti-inflammatory, antiviral, anticonvulsant, and anticancer agents highlights its importance in this industry.
Used in Dye Manufacturing:
2-cyano-N-phenethyl-acetamide is used as a chemical intermediate in the production of dyes, contributing to the coloration and quality of the final product.
Used in the Rubber Industry:
2-cyano-N-phenethyl-acetamide is utilized in the rubber industry, where it may serve as a component in the formulation of rubber products, potentially enhancing their properties or aiding in the manufacturing process.

InChI:InChI=1/C11H12N2O/c12-8-6-11(14)13-9-7-10-4-2-1-3-5-10/h1-5H,6-7,9H2,(H,13,14)

Upstream product

• 64-04-0 phenethylamine 
• 105-56-6 ethyl 2-cyanoacetate 
• 105-34-0 methyl 2-cyanoacetate 
• 156-28-5 2-phenylethylamine hydrochloride 
• 372-09-8 cyanoacetic acid 

Downstream Products

• 133550-38-6 AG 698 
• 21761-80-8 3-thia-pentane-1,2,4,5-tetracarboxylic acid tetraethyl ester 
• 204690-22-2 (Z)-2-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-(2-phenylethyl)ethanamide 
• 185739-20-2 2-(4-oxo-thiazolidin-2-ylidene)-N-phenethyl-acetamide 
• 673-79-0 diethyl 3,3'-thiobispropionate 
• 2090-25-7 tetraethyl 2,2'-dithiodisuccinate 
• 352555-43-2 3-amino-5-methyl-4-phenethylcarbamoyl-thiophene-2-carboxylic acid ethyl ester 
• 1276031-83-4 5-cyano-2-ethoxy-2-methyl-N-(2-phenylethyl)-1,3-dioxane-5-carboxamide 
• 1171006-45-3 2-cyano-2-(hydroxymethyl)-3-oxo-3-(2-phenethylamino)propyl acetate 
• 1354222-17-5 (Z)-(3-methyl-4-oxothiazolidin-2-ylidene)-N-(2-phenylethyl)ethanamide 

Relevant academic research and scientific papers

Non-alkylator anti-glioblastoma agents induced cell cycle G2/M arrest and apoptosis: Design, in silico physicochemical and SAR studies of 2-aminoquinoline-3-carboxamides

Malignant gliomas are the most common brain tumors, with generally dismal prognosis, early clinical deterioration and high mortality. Recently, 2-aminoquinoline scaffold derivatives have shown pronounced activity in central nervous system disorders. We herein reported a series of 2-aminoquinoline-3-carboxamides as novel non-alkylator anti-glioblastoma agents. The synthesized compounds showed comparable activity to cisplatin against glioblastoma cell line U87 MG in vitro. Among them, we found that 6a displayed good inhibitory activity against A172 and U118 MG glioblastoma cell lines and induced cell cycle arrest in the G2/M phase and apoptosis in U87 MG by flow cytometry analysis. Additionally, 6a displayed low cytotoxicity to several normal human cell lines. In silico study showed 6a had promising physicochemical properties and was predicted to cross the blood–brain barrier. Moreover, preliminary structure–activity relationships are also investigated, shedding light on further modifications towards more potent agents on this series of compounds. Our results suggest this compound has a promising potential as an anti-glioblastoma agent with a differential effect between tumor and non-malignant cells.

Structure-activity relationship of spop inhibitors against kidney cancer

Speckle-type POZ protein (SPOP) is overexpressed in the nucleus and misallocated in the cytoplasm in almost all the clear-cell renal cell carcinomas (ccRCCs), which leads to kidney tumorigenesis. Previously, we elucidated that the oncogenic SPOP-signaling pathway in ccRCC could be suppressed by 6b that inhibits SPOP-mediated protein interactions. Herein, we have established a structure-activity relationship for 6b analogues as SPOP inhibitors. Compound 6lc suppresses the viability and inhibits the colony formation of ccRCC cell lines driven by cytoplasmic SPOP, superior to 6b. Compound 6lc binds to the SPOP protein in vitro and disrupts SPOP binding to phosphatase-and-tensin homologue (PTEN) in HEK293T cells, which causes the observable phenomena: a decline in the ubiquitination of PTEN, elevated levels of both PTEN and dual-specificity phosphatase 7, and decreased levels of phosphorylated AKT and ERK when ccRCC cell lines are exposed to 6lc in a dose-response manner. Taken together, compound 6lc is a potent candidate against kidney tumorigenesis.

Promiscuity and selectivity in covalent enzyme inhibition: A systematic study of electrophilic fragments

Covalent ligand-target interactions offer significant pharmacological advantages. However, off-target reactivity of the reactive groups, which usually have electrophilic properties, must be minimized, and the selectivity of irreversible inhibitors is a crucial requirement. We therefore performed a systematic study to determine the selectivity of several electrophilic groups that can be used as building blocks for covalently binding ligands. Six reactive groups with modulated electrophilicity were combined with 11 nonreactive moieties, resulting in a small combinatorial library of 72 fragment-like compounds. These compounds were screened against a group of 11 enzyme targets to assess their selectivity and their potential for promiscuous binding to proteins. The assay results showed a considerably lower degree of promiscuity than initially expected, even for those members of the screening collection that contain supposedly highly reactive electrophiles.

4-phenyl-α-cyanocinnamic acid amide: Screening for a negative ion matrix for MALDI-MS imaging of multiple lipid classes

Matrix-assisted laser desorption/ionization imaging mass spectrometry (MALDI-IMS) has become a method of choice in lipid analysis, as it provides localization information for defined lipids that is not readily accessible with nonmass spectrometric methods. Most current MALDI matrices have been found empirically. Nevertheless, preferential matrix properties for many analyte classes are poorly understood and may differ between lipid classes. We used rational matrix design and semiautomated screening for the discovery of new matrices suitable for MALDI-IMS of lipids. Utilizing Smartbeam- and nitrogen lasers for MALDI, we systematically compared doubly substituted α-cyanocinnamic acid derivatives (R1-CCA-R2) with respect to their ability to serve as negative ion matrix for various brain lipids. We identified 4-phenyl-α-cyanocinnamic acid amide (Ph-CCA-NH 2) as a novel negative ion matrix that enables analysis and imaging of various lipid classes by MALDI-MS. We demonstrate that Ph-CCA-NH2 displays superior sensitivity and reproducibility compared to matrices commonly employed for lipids. A relatively small number of background peaks and good matrix suppression effect could make Ph-CCA-NH2 a widely applicable tool for lipid analysis.

Cyanoacetamides (IV): Versatile one-pot route to 2-quinoline-3-carboxamides

Cyanoacetic acid derivatives are the starting materials for a plethora of multicomponent reaction (MCR) scaffolds. Herein, we describe scope of a valuable general protocol for the synthesis of arrays of 2-aminoquinoline-3-carboxamides from cyanoacetamides and 2-aminobenzaldehydes or heterocyclic derivatives via a Friedlaender reaction variation. In many cases, the reactions involve a very convenient work up by simple precipitation and filtration. More than 40 new products are described. We foresee our protocol and the resulting derivatives becoming very valuable to greatly expanding the scaffold space of cyanoacetamide derivatives.

Cell-permeable iminocoumarine-based fluorescent dyes for mitochondria

A class of small molecule fluorophores, 2-iminocoumarin-3-carboxamide derivatives, has been developed by a rapid microwave-assisted process. These fluorescent probes are cell membrane permeable with low cytotoxicity and able to selectively stain organelles in living cells.

3-Acetyloxy-2-cyano-2-(alkylaminocarbamoyl)propyl groups as biodegradable protecting groups of nucleoside 5'-mono-phosphates

Thymidine 5'-bis[3-acetyloxy-2-cyano-2-(2-phenylethylcarbamoyl)propyl] phosphate (1) has been prepared and the removal of phosphate protecting groups by hog liver carboxyesterase (HLE) at pH 7.5 and 37 °C has been followed by HPLC. The first detectable intermediates are the (Rp)-and (S p)-diastereomers of the monodeacetylated triester 14, which subsequently undergo concurrent retro-aldol condensation to diester 4 and enzyme-catalyzed hydrolysis to the fully deacetylated triester 15. The former pathway predominates, representing 90% of the overall breakdown of 14. The diester 4 undergoes the enzymatic deacetylation 700 times less readily than the triester, but gives finally thymidine 5'-monophosphate as the desired main product. To elucidate the potential toxicity of the electrophilic 2-cyano-N-(2-phenylethyl)acrylamideby-product 17 released upon the deprotection, the hydrolysis of 1 has also been studied in the presence of glutathione (GSH).

NOVEL COMPOUNDS FOR MODULATING CELL PROLIFERATION

Novel styrylacrylonitrile compounds which are useful in treating a variety of cell proliferative disorders such as cancer are disclosed.

Synthesis of N-substituted γ-methylene γ-lactams

N-Substituted cyanoacetamides 1 were condensed with 1,2-diketones 2 under base catalysis to form ?-hydroxy ?-lactams 3. Treatment of 3 with acids gave novel fungicidal ?-methylene ?-lactams 4. The exocyclic double bond of 4b reacted reversibly with 4-toluene sulfinate. CSIRO 2005.

Modulators of LXR

Compounds, compositions and methods for modulating the activity of nuclear receptors are provided. In particular, heterocyclic compounds are provided for modulating the activity of nuclear receptors, including liver X receptor (LXR) and orphan nuclear receptors. In certain embodiments, the compounds are N-substituted pyridones.