51838-02-9

Basic information

• Product Name: 2-CYANO-N-PHENETHYL-ACETAMIDE
• Synonyms: 2-cyano-N-(2-phenylethyl)ethanamide
• CAS NO: 51838-02-9
• Molecular Formula: C₁₁H₁₂N₂O
• Molecular Weight: 188.23
• Mol File: 51838-02-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 432.2°Cat760mmHg
• Flash Point: 215.2°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 1.13E-07mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: 2-CYANO-N-PHENETHYL-ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CYANO-N-PHENETHYL-ACETAMIDE(51838-02-9)
• EPA Substance Registry System: 2-CYANO-N-PHENETHYL-ACETAMIDE(51838-02-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 51838-02-9(Hazardous Substances Data)

Usage

General Description

2-cyano-N-phenethyl-acetamide is a chemical compound of the Acetamide family with a molecular formula of C12H12N2O. 2-cyano-N-phenethyl-acetamide, also known as an Acetanilide derivative, plays an important role in various fields due to its diverse biological activities. It can act as a precursor for the synthesis of a wide array of bioactive molecules, including antifungal, antibacterial, analgesic, anti-inflammatory, antiviral, anticonvulsant, and anticancer agents amongst others. This makes it crucial in pharmaceutical and medicinal chemistry. This chemical is also utilized in the manufacture of dyes and in the rubber industry.

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 
• 156-28-5 2-phenylethylamine hydrochloride 
• 372-09-8 cyanoacetic acid 
• 105-34-0 methyl 2-cyanoacetate 

Downstream Products

• 1354222-17-5 (Z)-(3-methyl-4-oxothiazolidin-2-ylidene)-N-(2-phenylethyl)ethanamide 
• 1443772-30-2 (Z)-(3-methyl-1,4-dioxothiazolidin-2-ylidene)-N-(2-phenylethyl)ethanamide 
• 887613-79-8 (Z)-2-(5-methyl-4-oxothiazolidin-2-ylidene)-N-phenethylacetamide 
• 1373889-83-8 C₂₀H₁₅N₃O₃ 
• 1373889-56-5 6-amino-N-phenethyl-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide 
• 1373889-47-4 C₁₈H₁₅Br₂N₃O 
• 891602-23-6 7-(diethylamino)-2-imino-N-phenethyl-2H-chromene-3-carboxamide 
• 1171006-45-3 2-cyano-2-(hydroxymethyl)-3-oxo-3-(2-phenethylamino)propyl acetate 
• 1276031-83-4 5-cyano-2-ethoxy-2-methyl-N-(2-phenylethyl)-1,3-dioxane-5-carboxamide 
• 352555-43-2 3-amino-5-methyl-4-phenethylcarbamoyl-thiophene-2-carboxylic acid ethyl ester 
• 913819-76-8 5-hydroxy-4,5-dimethyl-2-oxo-1-(2-(phenyl)ethyl)-2,5-dihydro-1H-pyrrole-3-carbonitrile 
• 204690-22-2 (Z)-2-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-(2-phenylethyl)ethanamide 

Relevant articles and documents

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.

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.

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.