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Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-Benzyl-5-hydroxymethyl-2-pyrrolidinone is used as a reagent in the synthesis of pharmaceutical compounds, leveraging its potential biological activities and chemical versatility for the development of new medications.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-1-Benzyl-5-hydroxymethyl-2-pyrrolidinone serves as a versatile building block, facilitating the creation of a wide range of chemical compounds due to the ease of functionalization provided by the benzyl group.
Used in Biological Research:
(S)-1-Benzyl-5-hydroxymethyl-2-pyrrolidinone is utilized in biological research for studying its anti-inflammatory and analgesic effects, which may contribute to the discovery of novel therapeutic agents for pain management and inflammation control.

Upstream product

• 103301-78-6 methyl (2S)-1-benzyl-5-pyrrolidone-2-carboxylate 
• 56-86-0 L-glutamic acid 
• 100-52-7 benzaldehyde 
• 77539-18-5 (S)-(+)-2-benzylamino glutaric acid 
• 38854-94-3 N-benzyl-L-pyroglutamic acid 
• 98-79-3 L-Pyroglutamic acid 
• 4931-66-2 methyl (S)-pyroglutamate 

Downstream Products

• 138871-54-2 (S)-5-(tert-butyldiphenylsilyloxymethyl)-1-(phenylmethyl)-2-pyrrolidinone 
• 393810-27-0 (3R,5S)-1-Benzyl-3-fluoro-5-hydroxymethyl-pyrrolidin-2-one 
• 393810-22-5 (3R,5S)-1-Benzyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-fluoro-pyrrolidin-2-one 
• 1262796-53-1 (5S)-1-benzyl-5-(1H-2-methylimidazol-1-ylmethyl)-2-pyrrolidinone 

Relevant academic research and scientific papers

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.

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.

Synthesis, in silico docking experiments of new 2-pyrrolidinone derivatives and study of their anti-inflammatory activity

A new class of 2-pyrrolidinone derivatives was designed, synthesized, and tested for their antioxidant and anti-inflammatory activities. The compounds were evaluated for their inhibitory activity against LOX. The most potent among them, 14d [IC50 0.08 (±0.005) mM], and 14e [IC50 0.0705 (±0.003) mM], were also tested in vivo. The compound 14d induced equipotent inhibition against rat paw edema, which is very close to the effect produced by the commonly used standard, namely indomethacin (47%). The LOX inhibitory activity of the compound 14e proceeds in parallel to the % inhibitory value of lipid peroxidation meaning that this LOX inhibitory activity is supported by the lipid peroxidation inhibition. The molecular features that govern their bioactivity were explored through in silico docking experiments. The results showed that acidic moieties must be placed in certain distance and orientation in the active site of LOX enzyme in order to productively exhibit inhibitory activity. In addition, the 2-pyrrolidinone template significantly contributes in the inhibitory properties of the new compounds.

Synthesis, binding studies and in vivo biological evaluation of novel non-peptide antihypertensive analogues

AT1 antagonists (SARTANs) constitute the last generation of drugs for the treatment of hypertension, designed and synthesized to mimic the C-terminal segment of the vasoconstrictive hormone angiotensin II (AngII). They exert their action by blocking the binding of AngII on the AT1 receptor. Up to date eight AT1 antagonists have been approved for the regulation of high blood pressure. Although these molecules share common structural features and are designed to act under the same mechanism, they have differences in their pharmacological profiles and antihypertensive efficacy. Thus, there is still a need for novel analogues with better pharmacological and financial profiles. An example of a novel synthetic non peptide AT1 antagonist which devoids the classical template of SARTANs is MM1. In vivo studies showed that MMK molecules, which fall in the same class of MM1, had a significant antihypertensive (40-80% compared to the drug losartan) activity. However, in vitro affinity studies showed that losartan has considerably higher affinity. The theoretical docking studies showed that MM1 acts on the same site of the receptor as losartan. They exert hydrophobic interactions with amino acid Val108 of the third helix of the AT1 receptor and other hydrophobic amino acids in spatial vicinity. In addition, losartan favours multiple hydrogen bondings between its tetrazole group with Lys199. These additional interactions may in part explain its higher in vitro binding affinity.

Design and synthesis of novel antihypertensive drugs

AT1 antagonists constitute a new generation of drugs for the treatment of hypertension and are designed and synthesized to mimic the C-terminal segment of Angiotensin II (Ang II) and to block its binding action on AT1 receptor. For this reason, the conformational analysis of Ang II and its derivatives as well as the AT1 antagonists belonging to SARTANs class of molecules were studied. Such studies offer the possibility to reveal the stereoelectronic factors responsible for bioactivity of AT1 antagonists and to design and synthesize new analogues with better pharmacological and financial profiles. An example of a novel synthetic non-peptide molecule is given which mimics the His6-Pro7-Phe8 part of Ang II and is based on the (S)-pyroglutamic acid.

Diastereoselective alkylation of 1-benzyl-(5S)-substituted 2-pyrrolidinones

The (S)-glutamic acid derivatives, (5S)-methoxymethyl- and (5S)-benzyloxymethyl N-benzyl-2-pyrrolidinones, compounds 3a and 3b respectively, exhibit good to excellent diastereoselection upon alkylation with primary alkyl bromides or iodides.

Peptide Mimetics of Thyrotropin-Releasing Hormone Based on a Cyclohexane Framework: Design, Synthesis, and Cognition-Enhancing Properties

The design and synthesis of peptide mimetics of thyrotropin-releasing hormone (TRH) in which the peptide backbone is entirely replaced by a cyclohexane framework are described.The cis-1,3,5-trisubstituted ring was expected to permit key pharmacophoric gro

[(5-oxo)-2-pyrrolidinyl)methyl]cyclohexaneacetamides, compositions and use

[(5-oxo-2-pyrrolidinyl)methyl]cyclohexaneacetamides of the formula STR1 wherein R1 is hydrogen, lower alkyl or aryl-lower alkyl; R2 is hydrogen, lower alkyl, aryl, aryl-lower alkyl, STR2 wherein R5 and R6 are hydrogen, lower alkyl or aryl-lower alkyl; R3 and R4, independently, are hydrogen, lower alkyl, or aryl-lower alkyl; and enantiomers, diastereomers, and racemates thereof, and, when R2 is STR3 pharmaceutically acceptable acid addition salts thereof, are described. The compounds of formula I exhibit cognitive enhancement and antiamnestic activity and are therefore useful, for example, in treating memory deficits associated with Alzheimer's disease or age-associated memory impairment.