401567-01-9

Basic information

• Product Name: 3-{(2S,4S)-1-benzyloxycarbonyl-4-[4-(5-cyanobenzimidazol-2-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine
• Synonyms: 3-{(2S,4S)-1-benzyloxycarbonyl-4-[4-(5-cyanobenzimidazol-2-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine
• CAS NO: 401567-01-9
• Molecular Weight: 545.665
• Mol File: 401567-01-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-{(2S,4S)-1-benzyloxycarbonyl-4-[4-(5-cyanobenzimidazol-2-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-{(2S,4S)-1-benzyloxycarbonyl-4-[4-(5-cyanobenzimidazol-2-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine(401567-01-9)
• EPA Substance Registry System: 3-{(2S,4S)-1-benzyloxycarbonyl-4-[4-(5-cyanobenzimidazol-2-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine(401567-01-9)

Safety Data

• Hazardous Substances Data: 401567-01-9(Hazardous Substances Data)

Upstream product

• 401567-00-8 2-chlorobenzimidazole-5-carbonitrile 
• 401566-48-1 3-[(2S,4S)-1-benzyloxycarbonyl-4-(piperazin-1-yl)pyrrolidin-2-ylcarbonyl]thiazolidine 
• 401566-46-9 3-((S)-1-benzyloxycarbonyl-4-oxopyrrolidin-2-ylcarbonyl)thiazolidine 
• 401566-47-0 3-[(2S,4S)-1-benzyloxycarbonyl-4-(4-tert-butoxycarbonylpiperazin-1-yl)pyrrolidin-2-ylcarbonyl]thiazolidine 
• 17626-40-3 4-cyano-1,2-phenylenediamine 
• 197079-48-4 trans-N-(Benzyloxycarbonyl)-4-hydroxy-L-proline 

Relevant articles and documents

Fused bicyclic heteroarylpiperazine-substituted l-prolylthiazolidines as highly potent DPP-4 inhibitors lacking the electrophilic nitrile group

Hypoglycemic agents with a mechanism of depeptidyl peptidase IV (DPP-4) inhibition are suitable for once daily oral dosing. It is difficult to strike a balance between inhibitory activity and duration of action in plasma for inhibitors bearing an electrophilic nitrile group. We explored fused bicyclic heteroarylpiperazine substituted at the γ-position of the proline structure in the investigation of l-prolylthiazolidines lacking the electrophilic nitrile. Among them, 2-trifluoroquinolyl compound 8g is the most potent, long-lasting DPP-4 inhibitor (IC50 = 0.37 nmol/L) with high selectivity against other related peptidases. X-ray crystal structure determination of 8g indicates that CH-π interactions generated between the quinolyl ring and the guanidinyl group of Arg358 enhances the DPP-4 inhibitory activity and selectivity.