401565-08-0

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 4-[(4-cyanobenzoyl)oxy]-2-(3-thiazolidinylcarbonyl)-, 1,1-dimethylethyl ester, (2S,4S)-
• CAS NO: 401565-08-0
• Molecular Formula: C21H25N3O5S
• Molecular Weight: 431.513
• Mol File: 401565-08-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 4-[(4-cyanobenzoyl)oxy]-2-(3-thiazolidinylcarbonyl)-, 1,1-dimethylethyl ester, (2S,4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 4-[(4-cyanobenzoyl)oxy]-2-(3-thiazolidinylcarbonyl)-, 1,1-dimethylethyl ester, (2S,4S)-(401565-08-0)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 4-[(4-cyanobenzoyl)oxy]-2-(3-thiazolidinylcarbonyl)-, 1,1-dimethylethyl ester, (2S,4S)-(401565-08-0)

Safety Data

• Hazardous Substances Data: 401565-08-0(Hazardous Substances Data)

Upstream product

• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 401564-35-0 3-[(2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-pyrrolidinylcarbonyl]-1,3-thiazolidine 
• 401564-17-8 (2S,4S)-1-(tert-butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid 
• 401564-34-9 3-((2S,4S)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinylcarbonyl)-1,3-thiazolidine 
• 6068-72-0 4-cyanobenzoyl chlorIde 

Relevant articles and documents

Lead optimization of [(S)-γ-(arylamino)prolyl]thiazolidine focused on γ-substituent: Indoline compounds as potent DPP-IV inhibitors

Dipeptidyl peptidase IV (DPP-IV) inhibitors are looked to as a potential new antidiabetic agent class. A series of [(S)-γ-(arylamino)prolyl]thiazolidine compounds in which the electrophilic nitrile is removed are chemically stable DPP-IV inhibitors. To discover a structure for the γ-substituent of the proline moiety more suitable for interacting with the S2 pocket of DPP-IV, optimization focused on the γ-substituent was carried out. The indoline compound 22e showed a DPP-IV-inhibitory activity 100-fold more potent than that of the prolylthiazolidine 10 and comparable to that of NVP-DPP728. It also displayed improved inhibitory selectivity for DPP-IV over DPP8 and DPP9 compared to compound 10. Indoline compounds such as 22e have a rigid conformation with double restriction of the aromatic moiety by proline and indoline structures to promote interaction with the binding site in the S2 pocket of DPP-IV. The double restriction effect provides a potent inhibitory activity which compensates for the decrease in activity caused by removing the electrophilic nitrile.