2653-14-7

Basic information

• Product Name: N-BENZYL-2-CHLORO-N-PHENYLACETAMIDE
• Synonyms: MLS000721514;SMR000337137;ST5429185;ZINC01393099;N-BENZYL-2-CHLORO-N-PHENYLACETAMIDE;2-chloro-N-phenyl-N-(phenylmethyl)acetamide;2-chloro-N-phenyl-N-(phenylmethyl)ethanamide
• CAS NO: 2653-14-7
• Molecular Formula: C₁₅H₁₄ClNO
• Molecular Weight: 259.74
• Mol File: 2653-14-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-BENZYL-2-CHLORO-N-PHENYLACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYL-2-CHLORO-N-PHENYLACETAMIDE(2653-14-7)
• EPA Substance Registry System: N-BENZYL-2-CHLORO-N-PHENYLACETAMIDE(2653-14-7)

Safety Data

• Hazardous Substances Data: 2653-14-7(Hazardous Substances Data)

Upstream product

• 758640-21-0 N-Benzylaniline 
• 79-04-9 chloroacetyl chloride 
• 62-53-3 aniline 
• 100-52-7 benzaldehyde 
• 538-51-2 benzylidene phenylamine 
• 4015-58-1 monochloroacetic acid anhydride 

Downstream Products

• 928156-24-5 3,3,7,7-tetra[N-benzyl-N-phenyl(acetamide)-2-oxymethyl]-5-oxanonane 
• 1217-89-6 1-benzylisatin 
• 94445-31-5 [1-Ethoxy-2-methyl-1H-quinazolin-(4Z)-ylidene]-dithiocarbamic acid (benzyl-phenyl-carbamoyl)-methyl ester 
• 7135-32-2 1-benzylindolin-2-one 
• 76989-42-9 2-<(5-methyl-s-triazolo<4,3-c>quinazolin-3-yl)-thiol>-N,N-benzylphenylacetamide 
• 94445-30-4 5-methyl-1,2,4-thiadiazolo<2,3-c>-quinazolin-2-thione 
• 79143-76-3 [(Benzyl-phenyl-carbamoyl)-methyl]-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride 
• 857947-93-4 (2-dimethylamino-ethoxy)-acetic acid-(N-benzyl-anilide) 
• 861062-41-1 phenylsulfanyl-acetic acid-(N-benzyl-anilide) 

Relevant articles and documents

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Discovery of novel N -phenylphenoxyacetamide derivatives as EthR inhibitors and ethionamide boosters by combining high-throughput screening and synthesis

In this paper, we describe the screening of a 14640-compound library using a novel whole mycobacteria phenotypic assay to discover inhibitors of EthR, a transcriptional repressor implicated in the innate resistance of Mycobacterium tuberculosis to the second-line antituberculosis drug ethionamide. From this screening a new chemical family of EthR inhibitors bearing an N-phenylphenoxyacetamide motif was identified. The X-ray structure of the most potent compound crystallized with EthR inspired the synthesis of a 960-member focused library. These compounds were tested in vitro using a rapid thermal shift assay on EthR to accelerate the optimization. The best compounds were synthesized on a larger scale and confirmed as potent ethionamide boosters on M. tuberculosis-infected macrophages. Finally, the cocrystallization of the best optimized analogue with EthR revealed an unexpected reorientation of the ligand in the binding pocket.

Synthesis of substituted oxindoles from α-chloroacetanilides via palladium-catalyzed C - H functionalization

A novel method for the synthesis of oxindoles is described. In the presence of catalytic palladium acetate and 2-(di-tert-butylphosphino)biphenyl, α-chloroacetanilides are converted to oxindoles in good to excellent yields with high functional group compatibility using triethylamine as a stoichiometric base. The cyclization is highly regioselective, obviating the need for prefunctionalized arenes. Plausible mechanistic pathways for the reaction are discussed. Copyright