38854-94-3

Usage

Uses

Used in Pharmaceutical Research:
(R)-1-Benzyl-5-carboxy-2-pyrrolidinone is used as a building block for the synthesis of biologically active compounds, contributing to the development of new drugs and therapeutic agents. Its unique structure and properties make it a valuable tool in this industry, facilitating the creation of innovative pharmaceuticals.
Used in Organic Chemistry:
In the field of organic chemistry, (R)-1-Benzyl-5-carboxy-2-pyrrolidinone serves as a key intermediate in the synthesis of complex organic molecules. Its versatility and reactivity in chemical reactions make it an essential component in the development of novel organic compounds with potential applications in various industries.

Upstream product

• 90741-27-8 (S)-tert-butyl 1-benzyl-5-oxopyrrolidine-2-carboxylate 
• 100-39-0 benzyl bromide 
• 100-52-7 benzaldehyde 
• 4931-66-2 methyl (S)-pyroglutamate 
• 98-79-3 L-Pyroglutamic acid 
• 6893-26-1 D-Glutamic acid 
• 56-86-0 L-glutamic acid 
• 137641-62-4 (S)-(+)-1-(benzyl)-5-oxopyrrolidine-2-carboxylic acid ethyl ester 
• 35418-16-7 L-t-butyl pyroglutamate 
• 100-44-7 benzyl chloride 
• 103301-78-6 methyl (2S)-1-benzyl-5-pyrrolidone-2-carboxylate 
• 77539-18-5 (S)-(+)-2-benzylamino glutaric acid 

Downstream Products

• 438492-61-6 trans-4-cyclohexyl-N-benzyl-L-pyroglutamic acid 
• 438492-62-7 (2S,4S)-1-Benzyl-4-cyclohexyl-5-oxo-pyrrolidine-2-carboxylic acid benzyl ester 
• 438492-63-8 benzyl trans-4-cyclohexyl-5-thio-N-benzyl-L-pyroglutamate 
• 412352-95-5 4-{(S)-2-[((S)-1-Benzyl-5-oxo-pyrrolidine-2-carbonyl)-amino]-2-methoxycarbonyl-ethyl}-benzoic acid 
• 412353-01-6 (S)-2-[((S)-1-Benzyl-5-oxo-pyrrolidine-2-carbonyl)-amino]-3-[4-(piperazine-1-carbonyl)-phenyl]-propionic acid methyl ester 

Relevant academic research and scientific papers

Substituted 5-oxo-pyrrolidine derivative, and preparation method and applications thereof

The invention belongs to the technical field of medicine, relates to a substituted 5-oxo-pyrrolidine derivative disclosed in generation formula I, and a preparation method and applications thereof, and more specifically relates to applications of the substituted 5-oxo-pyrrolidine derivative in preparation of anti-cerebral ischemia medicines as a nerve protective agent, and a pharmaceutical composition taking the substituted 5-oxo-pyrrolidine derivative and a pharmaceutically acceptable salt of the substituted 5-oxo-pyrrolidine derivative as active components. The pharmaceutical composition contains the substituted 5-oxo-pyrrolidine derivative and a pharmaceutical excipient and/or a diluent of the substituted 5-oxo-pyrrolidine derivative. In the general formula I, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, X, Y, and n are defined in the patent specification and patent claims.

Discovery of ABT-957: 1-Benzyl-5-oxopyrrolidine-2-carboxamides as selective calpain inhibitors with enhanced metabolic stability

Aberrant activation of calpain has been observed in various pathophysiological disorders including neurodegenerative diseases such as Alzheimer's Disease. Here we describe our efforts on ketoamide-based 1-benzyl-5-oxopyrrolidine-2-carboxamides as a novel series of highly selective calpain inhibitors mitigating the metabolic liability of carbonyl reduction. The most advanced compound from this new series, namely A-1212805 (ABT-957, Alicapistat) proceeded to clinical phase I studies.

CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF

Disclosed herein are small molecule calpain modulator compositions, pharmaceutical compositions, the use and preparation thereof.

ANTIVIRAL COMPOUNDS

The present invention relates to novel compounds of general formula (I) wherein the groups X, and R1 to R4 have the meanings given in the description and claims, process for preparing these compounds and their use as for treating, preventing or ameliorating viral infections and their use for treating, preventing or ameliorating diseases which are associated with PLA2G16.

A the non-peptide class perishes weakly inhibiting protein antagonists and its synthetic method and application (by machine translation)

This invention discloses a kind of the non-peptide class perishes weakly inhibiting protein antagonist and method for preparing the same and application, which aims to provide a better anticancer effect with the non-peptide class perishes weakly inhibitin

3,7-DIAZABICYCLO[3.3.1 ]NONANE CARBOXAMIDES AS ANTITHROMBOTIC AGENTS

The present invention relates to the 3,7-diazabicyclo[3.3.1]nonane carboxamides and process for preparation thereof. The present invention further relates to the compounds of general formula (1) possessing anti-thrombotic (anti-platelet) activities. The invention also relates to use of these moieties as inhibitors of collagen induced platelet adhesion and aggregation mediated through collagen receptors both in vitro and in vivo. Further, invention also relates these class of compounds exhibiting anti-platelet efficacy through dual mechanism inhibited both collagen as well as U46619 (thromboxane receptor agonist) induced platelet aggregation. General formula (1) Wherein, R' is; wherein R is selected from alkyl, acyl, tosyl, tert-butyloxycarbonyl, araalkyl or substituted araalkyl groups; R'' is selected preferably from halogen, cyano, lower alkyl, aryl, substituted aryl, and tosyl groups; R1 is selected from hydrogen and lower alkyl groups; R2 is selected from lower alkyl and aryl groups; R3 is selected from tert-butyloxycarbonyl and bezyloxycarbonyl groups; n = 0,1.

An efficient and straight forward strategy for the synthesis of enantiomerically pure (S)-1-benzyl-5-(alkyl/aryl amino) methyl-pyrrolidin-2-ones

A simple, efficient and straightforward strategy for the synthesis of enantiomerically pure (S)-5-((alkyl/aryl amino) methyl)-pyrrolidin-2-ones from N-benzyl-5(S)-pyroglutaminol through Mitsunobu reaction has been described. These pyrrolidin-2-ones have great potential to act as asymmetric precursors for the synthesis of bioactive compounds/ natural products requiring suitably substituted aminomethyl group at C-5 of native pyrrolidin-2-ones.

Synthesis and identification of chiral aminomethylpiperidine carboxamides as inhibitor of collagen induced platelet activation

A series of chiral lactam carboxamides of aminomethylpiperidine were synthesized and investigated for the collagen induced in vitro anti-platelet efficacy and collagen plus epinephrine induced in vivo pulmonary thromboembolism. The compound 31a (30 μM/kg) displayed a remarkable antithrombotic efficacy (60% protection) which was sustained for more than 24 h and points to its excellent bioavailability. The compounds 31a (IC50 = 6.6 μM) and 32a (IC50 = 37 μM), as well as their racemic mixture 28i (IC50 = 16 μM) significantly inhibited collagen-induced human platelet aggregation in vitro. Compound 34c displayed dual mechanism of action against both collagen (IC50 = 3.3 μM) and U46619 (IC50 = 2.7 μM) induced platelet aggregation. The pharmacokinetic study of 31a indicated very faster absorption, prolonged and constant systemic exposure and thereby exhibiting better therapeutic response.

An efficient and straight forward synthesis of (5S)-1-benzyl-5-(1H- imidazol-1-ylmethyl)-2-pyrrolidinone (MM1): A novel antihypertensive agent

(5S)-1-benzyl-5-(1H-imidazol-1-ylmethyl)-2-pyrrolidinone and its closely related analog was synthesized from (S)-pyroglutaminol and imidazole or substituted imidazole using Mitsunobu reaction as the key step. Springer Science+Business Media, LLC 2010.

Discovery and structure-activity relationships of a series of pyroglutamic acid amide antagonists of the P2X7 receptor

A computational lead-hopping exercise identified compound 4 as a structurally distinct P2X7 receptor antagonist. Structure-activity relationships (SAR) of a series of pyroglutamic acid amide analogues of 4 were investigated and compound 31 was identified as a potent P2X7 antagonist with excellent in vivo activity in animal models of pain, and a profile suitable for progression to clinical studies.