56080-99-0

Usage

Uses

Used in Pharmaceutical Synthesis:
R-N-BENZYL-PROLINE is utilized as a key building block in the creation of various pharmaceuticals and biologically active molecules. Its unique structure and stereochemistry make it an essential component in the development of new drugs and therapeutic agents.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, R-N-BENZYL-PROLINE plays a significant role in drug discovery and development. Its specific stereochemistry allows for the design and synthesis of chiral molecules with potential therapeutic applications.
Used in Peptide-based Materials:
R-N-BENZYL-PROLINE has been investigated for its potential in the development of peptide-based materials. Its unique properties contribute to the creation of novel materials with potential applications in various industries.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
R-N-BENZYL-PROLINE has also been studied for its role as a chiral auxiliary in asymmetric synthesis. Its stereochemistry aids in the selective formation of enantiomers, which is crucial in the synthesis of chiral compounds with specific biological activities.

Upstream product

• 172478-10-3 (R)-N-benzylproline ethyl ester 
• 100-39-0 benzyl bromide 
• 344-25-2 D-Prolin 
• 100-44-7 benzyl chloride 

Downstream Products

• 113304-84-0 N-benzyl-(R)-(+)-proline methyl ester 
• 105024-93-9 (R)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide 
• 1346462-62-1 (R)-((S)-5-carbamoyl-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl) 1-benzylpyrrolidine-2-carboxylate 
• 702629-88-7 C₁₂H₁₄ClNO 
• 475150-69-7 (D)-1-benzylpyrrolidine-2-carboxylic acid{3-[spiro(isobenzofuran-1(3H),4'-piperidine)-1'-yl]propyl}amide 
• 1186302-27-1 1-benzylpyrrolidine-2-carboxylic acid {3-[4-(3-ethyl-2-oxo-2,3-dihydrobenzoimidazol-1-yl)piperidine-1-yl]propyl}amide 
• 1028924-72-2 (D)-1-benzylpyrrolidine-2-carboxylic acid {3-[4-(2,6-dichlorophenyl)piperidine-1-yl]propyl}amide 
• 1186302-21-5 (D)-1-benzylpyrrolidine-2-carboxylic-[3-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-8-yl)propyl]amide 
• 1186302-14-6 (D)-1-benzylpyrrolidine-2-carboxylic acid 3-{spiro[isobenzofuran-1(3H),4'-piperidine]-1'-yl}propyl ester 
• 130798-48-0 (R)-di-2-naphthylprolinol 

Relevant academic research and scientific papers

Discovery of novel n-substituted prolinamido indazoles as potent rho kinase inhibitors and vasorelaxation agents

Inhibitors of Rho kinase (ROCK) have potential therapeutic applicability in a wide range of diseases, such as hypertension, stroke, asthma and glaucoma. In a previous article, we described the lead discovery of DL0805, a new ROCK I inhibitor, showing potent inhibitory activity (IC50 6.7 μM). Herein, we present the lead optimization of compound DL0805, resulting in the discovery of 24- and 39-fold more-active analogues 4a (IC50 0.27 μM) and 4b (IC50 0.17 μM), among other active analogues. Moreover, ex-vivo studies demonstrated that 4a and 4b exhibited comparable vasorelaxant activity to the approved drug fasudil in rat aortic rings. The research of a preliminary structure-activity relationship (SAR) indicated that the target compounds containing a β-proline moiety have improved activity against ROCK I relative to analogues bearing an β-proline moiety, and among the series of the derivatives with a β-proline-derived indazole scaffold, the inhibitory activity of the target compounds with a benzyl substituent is superior to those with a benzoyl substituent.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF AUTONOMIC AND OTHER NEUROLOGICAL DISORDERS

The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for the treatment of autonomic and other neurological disorders may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of neurogenic orthostatic hypotension (NOH), as well as NOH associated with multiple system atrophy (MSA), familial amyloid polyneuropathy (FAP), pure autonomic failure (PAF), and Parkinson's disease (PD), intradialytic hypotension (IDH) or hemodialysis-induced hypotension, hypotension associated with fibromyalgia syndrome (FMS) and chronic fatigue syndrome (CFS).

NEPRILYSIN INHIBITORS

In one aspect, the invention relates to compounds having the formula I: where R1-R6 are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds have neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising these compounds; methods of using these compounds; and processes and intermediates for preparing these compounds.

NEPRILYSIN INHIBITORS

In one aspect, the invention relates to compounds having the formula (I): where R1-R6 are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds have neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising these compounds; methods of using these compounds; and processes and intermediates for preparing these compounds.

NEPRILYSIN INHIBITORS

In one aspect, the invention relates to compounds having the formula: where R1-R5 and X are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds have neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising such compounds; methods of using such compounds; and processes and intermediates for preparing such compounds.

The formation of pyrroline and tetrahydropyridine rings in amino acids catalyzed by pyrrolysine synthase (PylD)

The dehydrogenase PylD catalyzes the ultimate step of the pyrrolysine pathway by converting the isopeptide L-lysine-Nε-3R-methyl-D-ornithine to the 22nd proteinogenic amino acid. In this study, we demonstrate how PylD can be harnessed to oxidize various isopeptides to novel amino acids by combining chemical synthesis with enzyme kinetics and X-ray crystallography. The data enable a detailed description of the PylD reaction trajectory for the biosynthesis of pyrroline and tetrahydropyridine rings as constituents of pyrrolysine analogues.

NEPRILYSIN INHIBITORS

In one aspect, the invention relates to compounds having the formula: where R1-R6, a, b, and Z are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds have neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising such compounds; methods of using such compounds; and processes and intermediates for preparing such compounds.

AN IMPROVED PROCESS FOR THE PREPARATION OF (S)-10-ACETOXY-10,11-DIHYDRO-5H-DIBENZ[b,f]AZEPINE-5-CARBOXAMIDE

The present invention relates to a process for the preparation of (S)-10-acetoxy-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide compound of formula (1).

METHOD OF PREPARING OPTICALLY ACTIVE SERINE DERIVATIVE

A method of preparing L-threo-(2S,3R)-3-(3.4-dihydroxyphenyl)serine or a salt thereof and an immediate obtained in the preparation of the serine derivative are provided. The method includes decomposing an asymmetric aldol condensate of a chiral metal complex in a polar organic solvent using an acid and hydrogenating the resulting product.

METHOD FOR PRODUCING OPTICALLY ACTIVE SERINE DERIVATIVE

PROBLEM TO BE SOLVED: To provide a method for producing optically active L-threo-(2S,3R)-3-(3,4-dihydroxyphenyl)serine or salts thereof, and to provide an intermediate thereof. SOLUTION: The method for producing L-threo-(2S,3R)-3-(3,4-dihydroxyphenyl)serine or salts thereof comprises a step in which asymmetric aldol condensation products of chiral metal complex are decomposed to acids in a polar organic solvent, and a step in which hydroxylation reaction of the obtained products is performed. The chiral metal complex of a production intermediate of the optically active compound is e.g. 1-hydroxy-1-(3,4,-dibenzyloxyphenyl)glycine-Ni-D-2-[N(N'-benzylprolyl)amino]benzophenone.