5733-86-8

Usage

Uses

Used in Medicinal Chemistry:
1-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid is used as a building block for the synthesis of bioactive molecules, contributing to the development of new pharmaceutical agents.
Used in Drug Development:
1-BENZYL-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID is utilized in drug development for its potential biological activities, which may lead to the discovery of new therapeutic agents for the treatment of various diseases.
Used in Pharmaceutical Industry:
1-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid is used as a key intermediate in the synthesis of pharmaceuticals, enhancing the development of novel drugs with diverse applications in medicine.

InChI:InChI=1S/C12H13NO3/c14-11-6-10(12(15)16)8-13(11)7-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,15,16)

Upstream product

• 51535-00-3 methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate 
• 100-46-9 benzylamine 
• 256451-31-7 isopropyl N-benzylpyrrolidin-2-one-4-carboxylate 
• 617-52-7 Dimethyl itakonate 
• 97-65-4 2-methylenesuccinic acid 

Downstream Products

• 114368-05-7 1-benzyl-2-pyrrolidinone-4-carboxylic acid chloride 
• 51535-00-3 methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate 
• 191805-24-0 3-(1-benzyl-5-oxo-3-pyrrolidinyl)-5-(4-chlorophenyl)pyrazole 
• 154469-29-1 3-(1-benzyl-2-oxopyrrolidin-4-yl)-3-oxopropanoate 
• 107259-14-3 4-acetyl-1-benzyl-2-pyrrolidinone 
• 428518-42-7 (S)-(+)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylic acid 

Relevant academic research and scientific papers

Analgesic and anticancer activity of benzoxazole clubbed 2-pyrrolidinones as novel inhibitors of monoacylglycerol lipase

Ten benzoxazole clubbed 2-pyrrolidinones (11–20) as human monoacylglycerol lipase inhibitors were designed on the criteria fulfilling the structural requirements and on the basis of previously reported inhibitors. The designed, synthesized, and characterized compounds (11–20) were screened against monoacylglycerol lipase (MAGL) in order to find potential inhibitors. Compounds 19 (4-NO2 derivative) and 20 (4-SO2 NH2 derivative), with an IC50 value of 8.4 and 7.6 nM, were found most active, respectively. Both of them showed micromolar potency (IC50 value above 50 μM) against a close analogue, fatty acid amide hydrolase (FAAH), therefore considered as selective inhibitors of MAGL. Molecular docking studies of compounds 19 and 20 revealed that carbonyl of 2-pyrrolidinone moiety sited at the oxyanion hole of catalytic site of the enzyme stabilized with three hydrogen bonds (~2 ?) with Ala51, Met123, and Ser122, the amino acid residues responsible for the catalytic function of the enzyme. Remarkably, the physiochemical and pharmacokinetic properties of compounds 19 and 20, computed by QikProp, were found to be in the qualifying range as per the proposed guideline for good orally bioactive CNS drugs. In formalin-induced nociception test, compound 20 reduced the pain response in acute and late stages in a dose-dependent manner. They significantly demonstrated the reduction in pain response, having better potency than the positive control gabapentin (GBP), at 30 mg/kg dose. Compounds 19 and 20 were submitted to NCI, USA, for anticancer activity screening. Compounds 19 (NSC: 778839) and 20 (NSC: 778842) were found to have good anticancer activity on SNB-75 cell line of CNS cancer, exhibiting 35.49 and 31.88% growth inhibition (% GI), respectively.

ANALGESIC DRUG USING PAC1 RECEPTOR ANTAGONISTIC DRUG

This invention relates to an analgesic drug comprising a compound represented by the following formula (I) or (II), wherein R1 is a C1-6-alkoxy group or a C1-6-haloalkoxy group; R2 is a hydrogen atom; and R is an indazolyl group substituted with a halogen atom; a substituted or unsubstituted phenyl group; a pyrazolyl group; or a substituted or unsubstituted aralkyl group; or a salt thereof, or a solvate thereof.

Synthesis of a novel and potent small-molecule antagonist of PAC1 receptor for the treatment of neuropathic pain

We recently identified novel small-molecule antagonists of the PACAP type I (PAC1) receptor using docking-based in silico screening followed by in vitro/vivo pharmacological assays. In the present study, we synthesized 18 novel derivatives based on the structure of PA-9, a recently developed antagonist of the PAC1 receptor, with a view to obtain a panel of compounds with more potent antagonistic and analgesic activities. Among them, compound 3d showed improved antagonistic activities. Intrathecal injection of 3d inhibited both pituitary adenylate cyclase-activating polypeptide (PACAP) and spinal nerve ligation-induced mechanical allodynia. The effects were more potent than PA-9. Compound 3d also showed anti-allodynic effects following oral administration. Hence, our results suggest that 3d may become an orally available analgesic in the treatment of the neuropathic pain.

ANTIVIRAL COMPOUNDS

The present invention relates to novel compounds of general formula (I) wherein R1 to R4 and n 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.

Site-Specific Synthesis of β-Fluorinated γ-Butyrolactams via Decarboxylative Fluorination of β-Carboxyl-γ-Butyrolactams

Monofluorinated cyclic nitrogen-containing compounds are synthetically useful scaffolds in organic synthesis and medicinal applications. In this report, AgNO3 mediated decarboxylative fluorination of β-carboxyl-γ-butyrolactams using Selectfluor as a fluorine source was described to achieve a site-specific synthesis of β-fluorinated γ-butyrolactams.

PYRROLIDONE DERIVATIVES, OLIGOMERS AND POLYMERS

Simple organic structures, organic/inorganic polymers, and other substrates have been made, all of which have at least one pyrrolidone moiety present, and found to exhibit low toxicity, low complement activation features and may be used to reduce protein

1-benzyl-2- [...] -4-amide compound and its preparation method and application

The invention discloses 1-benzyl-2-pyrroline ketone-4-amide compounds represented by the general formula. According to independent R1, R2, R3, R4, R5, R6, R7, R8, R9 or R10, 1-3 C1-4 alkyl groups substituted by substituent groups are selected from a non-substituent C1-4 alkyl group, a non-substituent C1-3 alkoxy group, halogen, an amine sulfonyl group, a nitryl group and hydrogen or from halogen, a nitryl group, a C1-3 alkyl group and a C1-2 alkoxy group, or 1-3 C1-3 alkoxy groups substituted by substituent groups are selected from halogen, a nitryl group, a C1-3 alkyl group and a C1-2 alkyl group. The halogen is fluorine, chlorine or bromine. The invention further discloses a preparing method and application of the compounds. The compounds can restrain tyrosine kinase signal transduction and unhealthy cell hyperplasia and angiogenesis, and obvious curative effect is achieved on diseases such as tumors especially.

Inhibition of noroviruses by piperazine derivatives

There is currently an unmet need for the development of small-molecule therapeutics for norovirus infection. The piperazine scaffold, a privileged structure embodied in many pharmacological agents, was used to synthesize an array of structurally-diverse derivatives which were screened for anti-norovius activity in a cell-based replicon system. The studies described herein demonstrate for the first time that functionalized piperazine derivatives possess anti-norovirus activity. Furthermore, these studies have led to the identification of two promising compounds (6a and 9l) that can be used as a launching pad for the optimization of potency, cytotoxicity, and drug-like characteristics.

Intramolecular 1,6-addition to 2-pyridones. Mechanism and synthetic scope

Figure presented The scope and limitations of the intramolecular 1,6-addition of an enolate to a 2-pyridone moiety, a reaction that has found application in the synthesis of the lupin alkaloids, have been probed. This nucleophilic addition process has been shown to be reversible and favored in the case of (less stabilized) amide and lactam enolates, which readily form five- and six-membered bi-/tricyclic products. Alternative enolates (ketone, ester, thiolactam) and a variety of different acceptors (isoquinolinone, pyrimidinone, pyrazinone, pyridopyrazinone) have been evaluated, and a range of competing side reactions have been identified and characterized using various techniques, including in situ IR.

Synthesis of new β-trifluoromethyl containing GABA and β-fluoromethyl containing N-benzylpyrrolidinones

A whole series of 3-(mono-, di-, trifluoro)methyl-substituted N-benzylpyrrolidinones 5a-c was synthesized by deoxyfluorination of corresponding 3-functionalized N-benzylpyrrolidinones. New β-trifluoromethyl containing GABA 4a was obtained in two alternative ways: by successive hydrolysis and hydrogenolysis of 3-trifluoromethyl N-benzylpyrrolidinone 5a and from trifluoroacetone as starting compound.