854607-74-2

Basic information

• Product Name: 2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• Synonyms: 2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS NO: 854607-74-2
• Molecular Weight: 513.378
• Mol File: 854607-74-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester(854607-74-2)
• EPA Substance Registry System: 2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-(2,4-dichloro-5-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester(854607-74-2)

Safety Data

• Hazardous Substances Data: 854607-74-2(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 676559-42-5 methyl (5R)-5-((trimethylsilyl)ethynyl)-L-prolinate 
• 847943-35-5 (2S,5R)-N-tert-butoxycarbonyl-5-vinylpyrrolidine-2-carboxylic acid 
• 847943-39-9 (2S)-((2S)-cyanopyrrolidine-1-carbonyl)-5R-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 39489-77-5 2,4-dichloro-5-nitrophenol? 
• 328974-66-9 (2S,5R)-N-tert-butoxycarbonyl-5-vinylpyrrolidine-2-carboxylic acid methyl ester 
• 138958-09-5 cis-N-(methoxycarbonyl)-5-<2-(trimethylsilyl)ethynyl>-L-proline methyl ester 
• 847943-33-3 (2S,5R)-5-Trimethylsilanylethynyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 847943-34-4 (5R)-ethynylpyrrolidine-1,(2S)-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 847943-37-7 2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 847943-36-6 2S-(2S-cyano-pyrrolidine-1-carbonyl)-5R-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 847943-82-2 (2R)-(5-amino-2,4-dichloro-phenoxymethyl)-(5S)-((2S)-cyano-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Discovery, structure - Activity relationship, and pharmacological evaluation of (5-substituted-pyrrolidinyl-2-carbonyl)-2-cyanopyrrolidines as potent dipeptidyl peptidase IV inhibitors

A series of (5-substituted pyrrolidinyl-2-carbonyl)-2-cyanopyrrolidine (C5-Pro-Pro) analogues was discovered as dipeptidyl peptidase IV (DPPIV) inhibitors as a potential treatment of diabetes and obesity. X-ray crystallography data show that these inhibitors bind to the catalytic site of DPPIV with the cyano group forming a covalent bond with the serine residue of DPPIV. The C5-substituents make various interactions with the enzyme and affect potency, chemical stability, selectivity, and PK properties of the inhibitors. Optimized analogues are extremely potent with subnanomolar Ki's, are chemically stable, show very little potency decrease in the presence of plasma, and exhibit more than 1,000-fold selectivity against related peptidases. The best compounds also possess good PK and are efficacious in lowering blood glucose in an oral glucose tolerance test in ZDF rats.

Pharmaceutical compositions as inhibitors of dipeptidyl peptidase-IV (DPP-IV)

The present invention relates to compounds of formula (I), which inhibit dipeptidyl peptidase IV (DPP-IV) and are useful for the prevention or treatment of diabetes, especially type II diabetes, as well as hyperglycemia, syndrome X, hyperinsulinemia, β-cell failure, obesity, satiety disorders, atherosclerosis, and various immunomodulatory diseases.