1173169-85-1

Basic information

• Product Name: (S)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide
• Synonyms: (S)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide
• CAS NO: 1173169-85-1
• Molecular Weight: 204.272
• Mol File: 1173169-85-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide(1173169-85-1)
• EPA Substance Registry System: (S)-N-methyl-N-phenyl-pyrrolidine-2-carboxamide(1173169-85-1)

Safety Data

• Hazardous Substances Data: 1173169-85-1(Hazardous Substances Data)

Upstream product

• 111492-63-8 (S)-proline acid chloride hydrochloride 
• 100-61-8 N-methylaniline 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 

Downstream Products

• 1416973-98-2 (S,E)-1-(N,N'-dicyclohexylcarbamimidoyl)-N-methyl-N-phenylpyrrolidine-2-carboxamide 

Relevant articles and documents

Targeting the Src Homology 2 (SH2) Domain of Signal Transducer and Activator of Transcription 6 (STAT6) with Cell-Permeable, Phosphatase-Stable Phosphopeptide Mimics Potently Inhibits Tyr641 Phosphorylation and Transcriptional Activity

Signal transducer and activator of transcription 6 (STAT6) transmits signals from cytokines IL-4 and IL-13 and is activated in allergic airway disease. We are developing phosphopeptide mimetics targeting the SH2 domain of STAT6 to block recruitment to phosphotyrosine residues on IL-4 or IL-13 receptors and subsequent Tyr641 phosphorylation to inhibit the expression of genes contributing to asthma. Structure-affinity relationship studies showed that phosphopeptides based on Tyr631 from IL-4Rα bind with weak affinity to STAT6, whereas replacing the pY+3 residue with simple aryl and alkyl amides resulted in affinities in the mid to low nM range. A set of phosphatase-stable, cell-permeable prodrug analogues inhibited cytokine-stimulated STAT6 phosphorylation in both Beas-2B human airway cells and primary mouse T-lymphocytes at concentrations as low as 100 nM. IL-13-stimulated expression of CCL26 (eotaxin-3) was inhibited in a dose-dependent manner, demonstrating that targeting the SH2 domain blocks both phosphorylation and transcriptional activity of STAT6.

Proline imidazolidinones and enamines in Hajos-Wiechert and Wieland-Miescher ketone synthesis

Readily available aromatic prolinamides obtained from the acid chloride of proline hydrochloride and anilines induce large enantiomeric excesses in intramolecular aldol condensations. Imidazolidinones derived from the reaction of the catalyst and enamines