70571-31-2

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Benzylpiperidine-2,4-dione is utilized as a key building block in the synthesis of a variety of pharmaceuticals and bioactive molecules. Its unique structure allows for the creation of diverse compounds with potential therapeutic applications.
Used in Organic Synthesis:
As a versatile intermediate, 1-benzylpiperidine-2,4-dione is employed in organic synthesis for the preparation of complex organic molecules, contributing to the development of new chemical entities with specific properties and functions.
Used in Psychoactive Substance Synthesis:
1-Benzylpiperidine-2,4-dione serves as a precursor in the synthesis of certain psychoactive substances, highlighting its importance in the field of psychopharmacology and the study of mind-altering compounds.
Used in Parkinson's Disease Research and Therapy:
1-Benzylpiperidine-2,4-dione is studied for its potential as a therapeutic agent for Parkinson's disease. It acts as an inhibitor of the enzyme monoamine oxidase (MAO), which is implicated in the progression of the disease, offering a promising avenue for treatment development.

Upstream product

• 1257403-90-9 N-benzyl-5-methoxy-3,5-dioxopentan-1-aminium chloride 
• 100-46-9 benzylamine 
• 216372-98-4 methyl N-(benzyl)-N-(methylmalonoyl)-3-aminopropionate 
• 23574-01-8 3-benzylamino-propionic acid methyl ester 
• 182559-62-2 ethyl 3-[benzyl(3-ethoxy-3-oxopropyl)amino]-3-oxopropanoate 
• 23583-21-3 ethyl-3-benzylamino propionate 
• 1415042-73-7 1-benzyl-4-methoxy-5,6-dihydropyridin-2(1H)-one 
• 845267-78-9 tert-butyl 2,4-dioxopiperidine-1-carboxylate 
• 93758-46-4 methyl 1-benzyl-2,4-dioxo-3-piperidinecarboxylate 
• 108046-32-8 N-benzyl-4-hydroxypiperidin-2-one 

Downstream Products

• 31648-35-8 1-benzyl-3,3-dimethyl-2,4-piperidinedione 
• 99539-54-5 1-benzyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine 
• 1257403-91-0 1-benzyl-3-[(dimethylamino)methylidene]piperidine-2,4-dione 
• 1415042-81-7 1-Benzyl-3-(2-oxopropyl)piperidine-2,4-dione 
• 1433193-91-9 tert-butyl [2-(1-benzyl-6-oxo-1,2,3,6-tetrahydropyridin-4-yl)phenyl]carbamate 
• 1433193-92-0 4-(2-aminophenyl)-1-benzyl-3-bromo-5,6-dihydropyridin-2(1H)-one 
• 1433193-93-1 1-benzyl-3-bromo-4-[2-(tritylamino)phenyl]-5,6-dihydropyridin-2(1H)-one 
• 1433193-94-2 4-(2-aminophenyl)-1-benzyl-3-(2-chlorophenyl)-5,6-dihydropyridin-2(1H)-one 
• 1433193-95-3 1-{2-[1-benzyl-5-(2-chlorophenyl)-6-oxo-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(4-methoxyphenyl)urea 
• 1433193-96-4 1-{2-[1-benzyl-5-(2-chlorophenyl)-6-oxo-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(4-methoxybenzyl)urea 
• 1433193-90-8 1-benzyl-3-(2-chlorophenyl)-4-[2-(4-methoxyphenyliminomethyleneamino)phenyl]-5,6-dihydropyridin-2(1H)-one 
• 1433193-97-5 1-benzyl-3-(2-chlorophenyl)-4-[2-(4-methoxybenzyl)iminomethyleneaminophenyl]-5,6-dihydropyridin-2(1H)-one 

Relevant academic research and scientific papers

Selective synthesis of spiro and dispiro compounds using Mn(III)-based oxidation of tetracarbonyl compounds

The Mn(III)-based oxidation of methylenebis(cyclohexanedione)s and methylenebis(piperidinedione)s as a tetracarbonyl compound was investigated under various conditions, selectively producing spiro dihydrofurans and dispiro cyclopropanes depending on the solvent. The mechanism for the formation of the spiro dihydrofurans and dispiro cyclopropanes was discussed. In addition, a simple synthesis of a new type of alkaloid, 3,4,6,7,8,10-hexahydro-1H-pyrano[3,2-c:5,6-c’]dipyridine-1,9(2H)-diones, was demonstrated.

Palladium-Catalyzed Cyclocarbonylation of Pyridinylated Vinylogous Amides and Ureas to Generate Ring-Fused Pyridopyrimidinones

As part of a program aimed at generating new heterocyclic frameworks for medicinal chemistry exploration, an efficient approach to the assembly of novel ring-fused pyridopyrimidinones was undertaken. Specifically, a collection of 11H-pyrido[2,1-b]quinazoline-1,11(2H)-diones and 2,3-dihydropyrido[1,2-a]pyrrolo[3,4-d]pyrimidine-1,10-diones was generated via a palladium-catalyzed, pyridine-directed, cyclocarbonylation of 2-pyridyl-linked vinylogous amides and ureas in yields of up to 90%.

Structure-Guided Discovery of Potent and Selective Inhibitors of ERK1/2 from a Modestly Active and Promiscuous Chemical Start Point

There are a number of small-molecule inhibitors targeting the RAS/RAF/MEK/ERK signaling pathway that have either been approved or are in clinical development for oncology across a range of disease indications. The inhibition of ERK1/2 is of significant current interest, as cell lines with acquired resistance to BRAF and MEK inhibitors have been shown to maintain sensitivity to ERK1/2 inhibition in preclinical models. This article reports on our recent work to identify novel, potent, and selective reversible ERK1/2 inhibitors from a low-molecular-weight, modestly active, and highly promiscuous chemical start point, compound 4. To guide and inform the evolution of this series, inhibitor binding mode information from X-ray crystal structures was critical in the rapid exploration of this template to compound 35, which was active when tested in in vivo antitumor efficacy experiments.

Reactivity, Selectivity, and Stability in Sulfenic Acid Detection: A Comparative Study of Nucleophilic and Electrophilic Probes

The comparative reaction efficiencies of currently used nucleophilic and electrophilic probes toward cysteine sulfenic acid have been thoroughly evaluated in two different settings-(i) a small molecule dipeptide based model and (ii) a recombinant protein model. We further evaluated the stability of corresponding thioether and sulfoxide adducts under reducing conditions which are commonly encountered during proteomic protocols and in cell analysis. Powered by the development of new cyclic and linear C-nucleophiles, the unsurpassed efficiency in the capture of sulfenic acid under competitive conditions is achieved and thus holds great promise as highly potent tools for activity-based sulfenome profiling.

Synthetic study of perophoramidine: Construction of pentacyclic core structure via SmI2-mediated reductive cyclization

An intramolecular SmI2-mediated reductive cyclization of carbodiimides and unsaturated lactams was applied to functionalized substrates bearing tetrasubstituted olefins. The reaction afforded arylated spiro-2-iminoindolines in high yield. Although the stereochemistry of the product was different from the desired one, the optimized palladium-catalyzed aryl amidination realized the isomerization and C-N bond formation in a single step and resulted in efficient construction of pentacyclic core of perophoramidine synthetically equivalent to the Rainier's intermediate.

New CRTH2 Antagonists

The present invention relates to a compound of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.

Synthesis of 1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-ones as conformationally constrained pyrazole analogues of histamine

Three synthetic methods for the preparation of 1,5-disubstituted 1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-ones as heterocyclic histamine analogues were developed. The first method starts from easily available methyl 5-(2-aminoethyl)-1H-pyrazole-4-carboxylates, which were N-alkylated and the resulting secondary amines were cyclised in the presence of a base to give the title compounds in 17-92% yields (method A). Alternatively, the amines were first cyclised to the 5-unsubstituted pyrazolo[4,3-c]pyridin-4-ones. Subsequent N-benzylation afforded three of the title compounds in 36-49% yields (method B). The third method comprises a six-step transformation of methyl acrylate into 1-benzylpiperidine-2,4-dione. Treatment of the latter with N,N-dimethylformamide dimethylacetal (DMFDMA) followed by acid-catalysed cyclisation of the formed enaminone with methyl-, phenyl- and tert-butylhydrazine afforded the same three title compounds in 79-87% yields (method C). Georg Thieme Verlag Stuttgart New York.

SEROTONERGIC BENZOTHIOPHENES

The present invention provides serotonergic benzothiophenes of Formula (I), where A, R, R, R, R, and R are as described in the specification.

SEROTONERGIC BENZOFURANS

The present invention provides serotonergic benzofurans of Formula (I): where A, R, R, R, R, and R are as described in the specification.

Regio- and stereoselective hydroxylation of N-substituted piperidin-2-ones with Sphingomonas sp. HXN-200

High activity, excellent regioselectivity, and opposite enantioselectivity were achieved in the hydroxylation of N-benzyl- and N-tert-butoxycarbonylpiperidin-2-one with Sphingomonas sp. HXN-200. High yield preparations of 4-hydroxypiperidin-2-ones were demonstrated in a bioreactor and in a shaking flask by use of the frozen/thawed cells as biocatalyst. The absolute configuration for the bioproducts was established.