34622-39-4

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-2-PIPERIDINONE-6-CARBOXYLIC ACID is used as a reactant for the synthesis of various metabolites of lysine, which are developed during aging and in diabetic patients. These metabolites play a crucial role in understanding the metabolic changes associated with these conditions and can potentially lead to the development of new treatments.
Used in the Synthesis of Functionalized β-lactam N-heterocycles:
(S)-2-PIPERIDINONE-6-CARBOXYLIC ACID is used as a reactant for the synthesis of functionalized β-lactam N-heterocycles via carboxymethylproline synthase catalyzed cyclization reactions. These compounds have potential applications in the development of new antibiotics and other therapeutic agents.
Used in the Synthesis of Pro-(S)-C5 branched [4.3.1] aza-amide bicycles:
(S)-2-PIPERIDINONE-6-CARBOXYLIC ACID is used as a reactant to synthesize Pro-(S)-C5 branched [4.3.1] aza-amide bicycles, which are potential inhibitors for FK506-binding proteins. These inhibitors can be utilized in the development of immunosuppressive drugs and other therapeutic agents targeting protein-protein interactions.
Used in the Synthesis of Ethyl (S)-2-(6-oxopiperidin-2-yl)acetate:
(S)-2-PIPERIDINONE-6-CARBOXYLIC ACID is used as a reactant to synthesize Ethyl (S)-2-(6-oxopiperidin-2-yl)acetate, which can be reduced using LiBH4 to produce optically pure hydroxymethyl lactams. These hydroxymethyl lactams have potential applications in the development of various pharmaceutical compounds, including those with analgesic, anti-inflammatory, and anti-cancer properties.

InChI:InChI=1/C6H9NO3/c8-5-3-1-2-4(7-5)6(9)10/h4H,1-3H2,(H,7,8)(H,9,10)/t4-/m0/s1

Upstream product

• 47307-39-1 N^α-benzyloxycarbonyl-L-lysine isopropyl ester 
• 2389-60-8 Z-Lys(Boc)-OH 
• 83793-27-5 L-2-amino-5-<(benzyloxycarbonyl)carbamoyl>pentanoic acid 
• 102922-72-5 (S)-2-(((benzyloxy)carbonyl)amino)-6-hydroxyhexanoic acid 
• 24325-14-2 (2S)-2-[(phenylmethoxy)carbonyl]aminoadipic acid 
• 1155-64-2 N₆-[(benzyloxy)carbonyl]-L-lysine 
• 6033-32-5 (S)-2-amino-6-hydroxyhexanoic acid 
• 1118-90-7 L-homoglutamic acid 
• 82228-91-9 isopropyl α-benzyloxycarbonylamino-ε-oxohexanoate 
• 82228-90-8 N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-L-lysine isopropyl ester 
• 2418-95-3 (S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid 

Downstream Products

• 78664-72-9 L-pyro-2-aminoadipic acid pentafluorophenyl ester 
• 66537-55-1 <*>Aad-His-Tzl-NH2 
• 216301-91-6 diphenylmethyl (2S)-N-benzyloxycarbonyl-6-oxopipecolate 
• 259181-49-2 diphenylmethyl N-phenoxycarbonyl-6-oxopipecolate 
• 259181-47-0 diphenylmethyl N-tert-butoxycarbonyl-6-oxopipecolate 
• 259181-46-9 benzyl N-benzyloxycarbonyl-6-oxopipecolate 
• 259181-48-1 diphenylmethyl N-methoxycarbonyl-6-oxopipecolate 
• 259181-45-8 tert-butyl N-benzyloxycarbonyl-6-oxopipecolate 
• 259225-90-6 benzyl 6-oxopipecolate 
• 216315-22-9 diphenylmethyl (2S)-6-oxopipecolate 
• 128726-47-6 (+)-(S)-6-hydroxymethyl-2-piperidinone 
• 77897-79-1 <*>Aad-His(DNP)-Tzl-NH2 
• 197142-43-1 2-(tert-butyl-diphenylsilanyloxymethyl)-6-oxo-piperidine-1-carboxylic acid tert-butyl ester 
• 197142-46-4 3-(tert-butyl-diphenylsilanyloxymethyl)-2-aza-bicyclo[4.1.0]heptane-2-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE

Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

THERAPEUTICALLY ACTIVE COMPOUNDS AND USE THEREOF

Provided are therapeutically active compounds and the use in manufacture of medicaments for treating a cancer characterized by the presence of a mutant allele of IDH1.

THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE

Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

HEPATITIS C VIRUS INHIBITORS

The invention provides compounds of formulas (I) or (II): wherein the variables are defined in the specification, or a pharmaceutically-acceptable salt thereof, that are inhibitors of replication of the hepatitis C virus. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat hepatitis C viral infections, and processes and intermediates useful for preparing such compounds.

THERAPEUTICALLY ACTIVE COMPOSITIONS AND THEIR METHODS OF USE

Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE

Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.

Carboxymethylproline synthase catalysed syntheses of functionalised N-heterocycles

The utility of wild-type and variant carboxymethylproline synthases for biocatalysis was demonstrated by preparing functionalised 5-, 6- and 7-membered N-heterocycles from amino acid aldehydes and (alkylated) malonyl-coenzyme A derivatives; the N-heterocycles produced were converted to the corresponding bicyclic β-lactams by a carbapenem synthetase. The Royal Society of Chemistry 2010.

Synthesis of a new dual metalloprotease inhibitor. I. Diastereoselective alkylation of protected 6-oxopipecolic acid esters

Diastereoselective methylation of the enolate generated from various protected 6-oxopipecolic acid esters (3aa-3cd) was studied. The protecting groups on the carboxylic acid and amino groups significantly influenced the trans/cis selectivity in the methylation reaction. The optimal substrate (3ca), bearing benzhydryl ester and carbobenzyloxy moieties gave a trans/cis isomer ratio of ca. 4:1. Investigation of the reaction conditions revealed that the reaction solvent, alkylating reagent, and base employed to generate the enolate, were decisive factors for diastereoselectivity. Further optimization of reaction conditions, including the amounts of the reagents and their addition sequence enabled maximization of reaction conversion and minimization of by-products to produce the trans rich 5-methyl-6-oxopipecolic acid ester (4ca) on a large scale.

Hydrolytic cleavage of pyroglutamyl-peptide bond. I. The susceptibility of pyroglutamyl-peptide bond to dilute hydrochloric acid

The susceptibility of the pyroglutamyl-peptide bond in some biologically active peptides, dog neuromedin U-8 fragment (pGlu-Phe-Leu-Phe-Arg-Pro-Arg- OH), human big gastrin fragment (pGlu-Leu-Gly-Pro-OH) and thyrotropin releasing hormone (TRH) fragments (pGlu-His-Pro-OH, pGlu-His-OH), to 1 N HCl under mild conditions and/or at 60°C was studied. It was found that the N- terminal portion of pGlu-peptides is extremely labile to acid hydrolysis, giving not only the ring-opened product of the pyrrolidone moiety of the pGlu residue, but also the cleavage product of the pGlu-peptide linkage. The ring- opening reaction predominated over the cleavage reaction in hydrolysis of the four peptides in 1 N HCl at 60°C. The ring-opening reaction and the cleavage reaction of pGlu-peptide linkage proceeded faster than the cleavage of internal peptide bonds. The rate of hydrolysis was affected by the reaction temperature, and the ring-opening reaction was greatly diminished at 4°C in comparison with the cleavage reaction. Thus, the phenomenon that the pGlu- peptide bond is susceptible to dilute HCl as compared to the other peptide bonds appears to be a general one.

Synthesis of Thyrotropin-Releasing Hormone Analogues. 2. Tripeptides Structurally Greatly Differing from TRH with High Central Nervous System Activity

A new series of thyrotropin-releasing hormone (TRH) analogues, obtained by further modifications of our most potent central nervous system (CNS) stimulating neutral tripeptides at both termini, were synthesized by the pentafluorophenyl ester method and tested for CNS and thyrotropin (TSH) releasing activity.Replacement of pyroglutamic acid by pyro-2-aminoadipic acid, 2-oxoimidazolidine-4-carboxylic acid or γ-butyrolactone-γ-carboxylic acid and that of proline by pipecolic acid, thiazolidine-4-carboxylic acid, or homoproline in 2>- and 2>TRH led to tripeptides structurally widely different from TRH.In spite of this fact, 7 of the 17 analogues (1, 2, 8-10, 16, and 17) have stronger anticataleptic effect than TRH, with negligible or no hormonal potency.The highest CNS activity was achieved when pyroglutamic acid was replaced by pyro-2-aminoadipic acid at the N-terminus .A novel synthesis of L-2-aminoadipic acid suitable for large-scale preparation is also described.