204387-54-2

Basic information

• Product Name: (2S)-Pyrrolidine-2-carbonitrile p-toluene sulfonate
• Synonyms: (2S)-Pyrrolidine-2-carbonitrile p-toluene sulfonate;(2S)-2-pyrrolidinecarbonitrile 4-methylbenzenesulfonate
• CAS NO: 204387-54-2
• Molecular Weight: 268.337
• Mol File: 204387-54-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2S)-Pyrrolidine-2-carbonitrile p-toluene sulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-Pyrrolidine-2-carbonitrile p-toluene sulfonate(204387-54-2)
• EPA Substance Registry System: (2S)-Pyrrolidine-2-carbonitrile p-toluene sulfonate(204387-54-2)

Safety Data

• Hazardous Substances Data: 204387-54-2(Hazardous Substances Data)

Usage

General Description

(2S)-Pyrrolidine-2-carbonitrile p-toluene sulfonate is a chemical compound that is commonly used in organic synthesis. It is a derivative of pyrrolidine and is often utilized as a building block in the creation of various pharmaceuticals and agrochemicals. Its p-toluene sulfonate salt form improves its solubility and stability, making it easier to handle in laboratory settings. (2S)-Pyrrolidine-2-carbonitrile p-toluene sulfonate has a wide range of potential applications, including as a reagent in the preparation of heterocyclic compounds and in the synthesis of drug candidates. Its unique structure and properties make it a valuable tool in the field of organic chemistry.

Upstream product

• 147-85-3 L-proline 
• 35150-07-3 (S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 104-15-4 toluene-4-sulfonic acid 
• 228244-04-0 tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate 

Downstream Products

• 872341-97-4 [(S)-1-Biphenyl-4-ylmethyl-2-((S)-2-cyano-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 1390623-33-2 (S)-1-(2-benzyl-3-oxoisoindoline-4-carbonyl)pyrrolidine-2-carbonitrile 
• 207557-35-5 (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile 
• 934471-42-8 tert-butyl (2S,4R)-2-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-4-[2,6-diethoxy-4-(methoxymethoxy)phenyl]-1-pyrrolidinecarboxylate 

Relevant articles and documents

Synthesis and Hypoglycemic Activity of Aryl(Hetaryl)Propenoic Cyanopyrrolidine Amides

Abstract: A series of amides based on (2S)-cyanopyrrolidine and α, β-unsaturated aryl- and hetarylcarboxylic acids have been synthesized. The dependence of the hypoglycemic activity of compounds on the structure of the aromatic fragment has been studied in the oral glucose tolerance test in mice. Amides based on (E)-3-phenylprop-2-enoic and (E)-3-(4-methoxyphenyl)prop-2-enoic acids and (2S)-cyanopyrrolidine have been shown to significantly reduce blood glucose levels in mice. The observed hypoglycemic effect at a dose of 10 mg/kg is comparable to the effect of hypoglycemic drug vildagliptin.

Synthesis and biological evaluation of pyrrolidine-2-carbonitrile and 4-fluoropyrrolidine-2-carbonitrile derivatives as dipeptidyl peptidase-4 inhibitors for the treatment of type 2 diabetes

A novel series of pyrrolidine-2-carbonitrile and 4-fluoropyrrolidine-2- carbonitrile derivatives was designed, synthesized, and found to act as dipeptidyl peptidase-4 (DPP-4) inhibitors. From this series of compounds, compound 17a was identified as an efficacious, safe, and selective inhibitor of DPP-4. In vivo studies in ICR and KKAy mice showed that administration of this compound resulted in decreased blood glucose in these mice after an oral glucose challenge. Compound 17a showed high DPP-4 inhibitory activity (IC50 = 0.017 μM), moderate selectivity against DPP-4 (selective ratio: DPP-8/DPP-4 = 1324; DPP-9/DPP-4 = 1164), and good efficacy in oral glucose tolerance tests in ICR and KKAy mice. These in vivo anti-diabetic properties and its desirable pharmacokinetic profile in Sprague-Dawley rats demonstrate that compound 17a is a promising candidate for development as an anti-diabetic agent.