193693-69-5

Usage

Uses

Used in Organic Synthesis:
(S)-1-N-Cbz-3-cyanopyrrolidine is used as a key intermediate in organic synthesis for the preparation of various pharmaceuticals and biologically active molecules. Its pyrrolidine scaffold and functional groups enable the formation of diverse chemical entities through a range of reactions, such as nucleophilic addition, reductive amination, and cross-coupling reactions.
Used in Drug Discovery:
In the pharmaceutical industry, (S)-1-N-Cbz-3-cyanopyrrolidine serves as a valuable building block for the development of novel drug candidates. Its chiral nature and versatile functional groups allow for the design and synthesis of enantioselective compounds with potential therapeutic applications. The pyrrolidine core is a common structural motif in many drugs, making (S)-1-N-Cbz-3-cyanopyrrolidine a promising starting material for medicinal chemistry research.
Used in Chiral Pool Synthesis:
(S)-1-N-Cbz-3-cyanopyrrolidine is utilized as a chiral pool compound in the synthesis of enantiomerically pure compounds. Its (S)-1 configuration provides a valuable source of chirality, which can be incorporated into target molecules through various synthetic transformations. This approach is particularly useful in the preparation of enantioselective catalysts, ligands, and pharmaceutical agents.
Used in Protecting Group Chemistry:
The N-tert-butoxycarbonyl protecting group in (S)-1-N-Cbz-3-cyanopyrrolidine plays a crucial role in protecting the amine functionality during synthetic transformations. This feature is particularly useful in the synthesis of complex molecules, where selective protection and deprotection of functional groups are required to achieve the desired product. The use of (S)-1-N-Cbz-3-cyanopyrrolidine in protecting group chemistry allows for the controlled assembly of molecular structures with precise functional group placement.

Upstream product

• 100858-33-1 (3R)-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester 
• 501-53-1 benzyl chloroformate 
• 188846-99-3 (+/-)-3-cyanopyrrolidine-1-carboxylic acid benzyl ester 
• 122536-68-9 (R)-3-<(methylsulfonyl)oxy>-1-pyrrolidinecarboxylic acid phenylmethyl ester 
• 151-50-8 potassium cyanide 
• 136725-51-4 benzyl (3R)-3-(p-tolylsulfonyloxy)pyrrolidine-1-carboxylate 

Downstream Products

• 192214-00-9 (S)-1-((benzyloxy)carbonyl)pyrrolidine-3-carboxylic acid 
• 72580-53-1 (S)-(+)-3-pyrrolidinecarboxylic acid 
• 573704-57-1 (+)-(S)-3-carbamidopyrrolidine-1-carboxylic acid benzyl ester 
• 1352661-06-3 C₁₅H₂₀N₂O₃ 
• 1352661-21-2 C₁₅H₁₉N₃O₄ 
• 1352660-07-1 C₂₉H₄₀N₄O₆Si 
• 1352660-09-3 C₂₃H₂₆N₄O₆ 
• 1352660-16-2 C₁₇H₁₈N₂O₆ 
• 1352660-17-3 C₁₃H₁₇N₃O₅S 
• 1352660-19-5 C₂₉H₄₃N₅O₉SSi 
• 1124369-40-9 (S)-pyrrolidine-3-carboxylic acid hydrochloride 
• 573704-64-0 (3S)-pyrrolidine-3-carboxamide 

Relevant academic research and scientific papers

CARBAPENEM ANTIBACTERIALS WITH GRAM-NEGATIVE ACTIVITY

The present invention provides β-methyl carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections and methods for treating such infections using such compounds and/or compositions. The invention includes administering an effective amount of a carbapenem compound or salt and/or prodrug thereof to a host in need of such a treatment.

Nitrilase-catalyzed enantioselective synthesis of pyrrolidine- And piperidinecarboxylic acids

The enantioselective synthesis of the nonproteinogenic amino acids β-proline and nipecotic acids from their readily available nitriles is achieved in high enantiomeric excess by commercially available nitrilases. The presented procedure comprises not more than 4 steps, thus considerably reducing the multiple steps generally required. Amide formation is also observed for specific heterocyclic nitriles.

PYRROLIDINE DERIVATIVES AS HISTAMINE RECEPTORS LIGANDS

The present invention relates to pyrrolidine derivatives of formula (I) having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of neurological and psychiatric disorders.

Synthesis of potent oxindole CDK2 inhibitors

A series of oxindole CDK2 inhibitors was synthesized. These novel analogues have a saturated monosubstituted cyclic moiety at their C-4 position that mimics the ribofuranoside of ATP. This substitution afforded agents with increased potency relative to th

Stability against enzymatic hydrolysis of endomorphin-1 analogues containing β-proline

The enantiomer of endomorphin-1 (Tyr-Pro-Trp-PheNH2) and the analogues containing (S)-or (R)-β-proline have been synthesized, and their affinities towards μ-opioid receptors have been measured. As expected, the incubations of the different peptides with some commercially available enzymes showed that the presence of D-residues gave strong resistance towards digestion. The presence of β-proline alone is sufficient to confer good resistance against the hydrolysis of the biologically strategic Pro-Trp bond.

Synthesis and binding activity of endomorphin-1 analogues β-amino acids

Endomorphin-1 (Tyr-Pro-Trp-PheNH2) has been proposed as the most potent endogenous ligand of the μ-opioid receptors. In this paper, we describe the synthesis of some endomorphin-1 based tetrapeptides in which a residue of the sequence Tyr-Pro-Trp-PheNH2 is replaced by the corresponding β-isomer. These novel peptides showed different affinities for the opioid receptors labeled with [3H]-DAMGO in rat brain membranes, depending on the β-amino acid. In particular, the tetrapeptide containing β-Pro (Tyr-β-(R)-Pro-Trp-PheNH2) displayed a higher affinity than endogenous endomorphin-1, as revealed by their K(i) values (0.33 and 11.1 nM, respectively). (C) 2000 Elsevier Science Ltd.

Constrained β-alanine based GpIIb/IIIa antagonists

The concepts of centrally constrained and peptide based fibrinogen receptor antagonists have been successfully combined into a single series of analogs which have been demonstrated to be potent inhibitors of platelet aggregation.