121147-97-5

Usage

Uses

Used in Pharmaceutical Industry:
(2S-trans)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-DiMethylethyl) 2-Methyl Ester is used as a key intermediate in the synthesis of neuronal nitric oxide synthase inhibitors. These inhibitors play a crucial role in regulating the production of nitric oxide in the nervous system, which is essential for maintaining proper neuronal function and has been linked to various neurological disorders. By modulating nitric oxide levels, these inhibitors can potentially be used to treat conditions such as Alzheimer's disease, Parkinson's disease, and other neurodegenerative disorders.
Chemical Properties:
(2S-trans)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-DiMethylethyl) 2-Methyl Ester is a yellow oil, which suggests that it is a viscous liquid at room temperature. This characteristic, along with its chemical composition, makes it a suitable candidate for use in the development of pharmaceutical compounds. The presence of the azido group in its structure also indicates its potential reactivity and versatility in chemical reactions, further enhancing its utility in the synthesis of various compounds.

Upstream product

• 146060-25-5 O2-methyl O1-tert-butyl (2S,4S)-4-(p-tolylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 121147-93-1 (2S,4S)-2-methyl N-Boc-4-((methylsulfonyl)oxy)pyrrolidine-2-carboxylate 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 87250-97-3 2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 121147-94-2 1-tert-butyl 2-methyl (2S,4S)-4-((benzoyl)oxy)-1,2-pyrrolidinedicarboxylate 
• 40350-82-1 1-(t-butoxycarbonyl)-4-hydroxyproline 
• 124-63-0 methanesulfonyl chloride 
• 84520-68-3 N-tert-butoxycarbonyl-cis-4-azido-L-proline methyl ester 
• 88043-21-4 (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 

Downstream Products

• 121148-00-3 1-(1,1-dimethylethyl) 2-methyl (2S,4R)-4-amino-1,2-pyrrolidinedicarboxylate 
• 121148-10-5 tert-butyl (2S,4R)-2-formyl-4-((phenylsulfonyl)amino)-pyrrolidine-1-carboxylate 
• 121148-21-8 tert-butyl (2S,4R)-2-formyl-4-(((4-methylphenyl)sulfonyl)amino)pyrrolidine-1-carboxylate 
• 121148-09-2 tert-butyl (2S,4R)-2-formyl-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidine-1-carboxylate 
• 121148-22-9 tert-butyl (2S,4R)-2-formyl-4-(((4-methoxyphenyl)sulfonyl)amino)pyrrolidine-1-carboxylate 
• 121148-05-8 4(R)-[(phenylsulfonyl)amino]-1,2(S)-pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl)-2-methyl ester 
• 121148-18-3 1-tert-butyl 2-methyl (2S,4R)-4-(((4-methylphenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate 
• 121148-04-7 1-tert-butyl 2-methyl (2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate 
• 121148-19-4 1-tert-butyl 2-methyl (2S,4R)-4-(((4-methoxyphenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate 
• 121148-23-0 tert-butyl (2S,4R)-2-formyl-4-(((4-(trifluoromethyl)phenyl)sulfonyl)amino)pyrrolidine-1-carboxylate 
• 121147-40-8 methyl 3-((Z)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate 
• 121147-41-9 methyl 3-((E)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate 
• 121147-39-5 methyl 4-((Z)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate 
• 121147-58-8 methyl 4-((E)-2-((2S,4R)-4-(((4-chlorophenyl)sulfonyl)amino)pyrrolidin-2-yl)ethenyl)benzoate 

Relevant academic research and scientific papers

Functionalizable oligoprolines as molecular scaffolds

Azidoproline (Azp) containing oligoprolines are conformationally well-defined, helical molecular scaffolds that allow for facile functionalization. Within this article we describe the synthesis of Azp-containing oligoprolines and different strategies to introduce functional moieties. In addition, the influence of factors such as substituents at the γ-position of proline as well as functional groups at the termini on the conformational stability of the molecular scaffolds are briefly presented. Schweizerische Chemische Gesellschaft.

Azidoproline containing helices: Stabilization of the polyproline II structure by a functionalizable group

The conformation and functionalizability of 4-azidoproline containing polyprolines was studied. The conformational analyses demonstrate that the PPII helix is stabilized by (4R)Azp and destabilized by (4S)Azp. Functionalization of Azp containing polyprolines was accomplished efficiently in a differential fashion by "click chemistry", rendering Azp containing polyprolines attractive molecular scaffolds. Copyright

Design and synthesis of fluorinated peptides for analysis of fluorous effects on the interconversion of polyproline helices

The unique interaction between fluorine atoms has been exploited to alter protein structures and to develop synthetic and analytical applications. To expand such fluorous interaction for novel applications, polyproline peptides represent an excellent molecular nanoscaffold for controlling the presentation of perfluoroalkyl groups on their unique secondary structure. We develop approaches to synthesis fluorinated peptides to systematically investigate how the number, location and types of the fluorous groups on polyproline affect the conformation by monitoring the transition between the two major polyproline structures PPI and PPII. This work provides valuable information on how fluorous interaction affects the peptide structure and also benefits the design of functional fluorous molecules.

Multipodal insulin mimetics built on adamantane or proline scaffolds

Multi-orthogonal molecular scaffolds can be applied as core structures of bioactive compounds. Here, we prepared four tri-orthogonal scaffolds based on adamantane or proline skeletons. The scaffolds were used for the solid-phase synthesis of model insulin mimetics bearing two different peptides on the scaffolds. We found that adamantane-derived compounds bind to the insulin receptor more effectively (Kd value of 0.5 μM) than proline-derived compounds (Kd values of 15–38 μM) bearing the same peptides. Molecular dynamics simulations suggest that spacers between peptides and central scaffolds can provide greater flexibility that can contribute to increased binding affinity. Molecular modeling showed possible binding modes of mimetics to the insulin receptor. Our data show that the structure of the central scaffold and flexibility of attached peptides in this type of compound are important and that different scaffolds should be considered when designing peptide hormone mimetics.

Altering the sex pheromone cyclo(L-pro-l-pro) of the diatom seminavis robusta towards a chemical probe

As a major group of algae, diatoms are responsible for a substantial part of the primary production on the planet. Pennate diatoms have a predominantly benthic lifestyle and are the most species-rich diatom group, with members of the raphid clades being motile and generally having heterothallic sexual reproduction. It was recently shown that the model species Seminavis robusta uses multiple sexual cues during mating, including cyclo(L-Pro-L-Pro) as an attraction pheromone. Elaboration of the pheromone-detection system is a key aspect in elucidating pennate diatom life-cycle regulation that could yield novel fundamental insights into diatom speciation. This study reports the synthesis and bio-evaluation of seven novel pheromone analogs containing small structural alterations to the cyclo(L-Pro-L-Pro) pheromone. Toxicity, attraction, and interference assays were applied to assess their potential activity as a pheromone. Most of our analogs show a moderate-to-good bioactivity and low-to-no phytotoxicity. The pheromone activity of azide-and diazirine-containing analogs was unaffected and induced a similar mating behavior as the natural pheromone. These results demonstrate that the introduction of confined structural modifications can be used to develop a chemical probe based on the diazirine-and/or azide-containing analogs to study the pheromone-detection system of S. robusta.

N-(1-CYANO-PYRROLIDIN-3-YL)-5-(3-(TRIFLUOROMETHYL)PHENYL)OXAZOLE-2-CARBOXAMIDE DERIVATIVES AND THE CORRESPONDING OXADIAZOLE DERIVATIVES AS USP30 INHIBITORS FOR THE TREATMENT OF MITOCHONDRIAL DYSFUNCTION

The present invention relates to a class of N-cyanopyrrolidines with activity as inhibitors of the deubiquitylating enzyme USP30, having utility in a variety of therapeutic areas, including conditions involving mitochondrial dysfunction, cancer and fibros

Design, Synthesis, and Biochemical Evaluation of Alpha-Amanitin Derivatives Containing Analogs of the trans-Hydroxyproline Residue for Potential Use in Antibody-Drug Conjugates

Alpha-amanitin, an extremely toxic bicyclic octapeptide extracted from the death-cap mushroom, Amanita phalloides, is a highly selective allosteric inhibitor of RNA polymerase II. Following on growing interest in using this toxin as a payload in antibody-drug conjugates, herein we report the synthesis and biochemical evaluation of several new derivatives of this toxin to probe the role of the trans-hydroxyproline (Hyp), which is known to be critical for toxicity. This structure activity relationship (SAR) study represents the first of its kind to use various Hyp-analogs to alter the conformational and H-bonding properties of Hyp in amanitin.

SUBSTITUTED CYANOPYRROLIDINES WITH ACTIVITY AS USP30 INHIBITORS

The present invention relates to a class of substituted-cyanopyrrolidines with activity as inhibitors of the deubiquitylating enzyme USP30, having utility in a variety of therapeutic areas, including conditions involving mitochondrial dysfunction, cancer

SUBSTITUTED CYANOPYRROLIDINES WITH ACTIVITY AS USP30 INHIBITORS

The present invention relates to a class of substituted-cyanopyrrolidines with activity as inhibitors of the deubiquitylating enzyme USP30, having utility in a variety of therapeutic areas, including conditions involving mitochondrial dysfunction, cancer and fibrosis: (I).

ARGINASE INHIBITORS AND METHODS OF USE THEREOF

Disclosed are compounds of formula (Ia) or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of formula (Ia) and methods of using the same for treating cancer or a respiratory inflammatory disease and inhibiting arginase, wherein R1 is -NHR1a; R1a is -H or -C(O)CH(R1b)NHR1c; and R1b is selected from -H, -(C1-C4 ) alkyl and CH2OR1d and R1cis -H; or R1b and R1c, together with the atom to which they are attached, form a 5-membered heterocyclic ring; and R1d is H or -CH3.