129823-21-8

Basic information

• Product Name: 2,5-Pyrrolidinedione,3-(acetyloxy)-1-(phenylmethyl)-, (3S)-
• Synonyms: 2,5-Pyrrolidinedione,3-(acetyloxy)-1-(phenylmethyl)-, (S)-; (S)-3-Acetoxy-N-benzyl-2,5-dioxopyrrolidine
• CAS NO: 129823-21-8
• Molecular Formula: C13H13 N O4
• Molecular Weight: 247.251
• Mol File: 129823-21-8.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 2,5-Pyrrolidinedione,3-(acetyloxy)-1-(phenylmethyl)-, (3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Pyrrolidinedione,3-(acetyloxy)-1-(phenylmethyl)-, (3S)-(129823-21-8)
• EPA Substance Registry System: 2,5-Pyrrolidinedione,3-(acetyloxy)-1-(phenylmethyl)-, (3S)-(129823-21-8)

Safety Data

• Hazardous Substances Data: 129823-21-8(Hazardous Substances Data)

Usage

Physical State

Crystalline solid

Molecular Weight

271.314 g/mol

Main Application

Intermediate in pharmaceutical synthesis

Specific Use

Production of antipsychotics and antidepressants

Additional Properties

Exhibits anti-inflammatory and analgesic properties

Industry

Valuable ingredient in pharmaceutical manufacturing

Upstream product

• 75-36-5 acetyl chloride 
• 78027-57-3 (RS)-N-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 2174-58-5 L-malic acid 
• 100-46-9 benzylamine 
• 59025-03-5 (S)-acetoxysuccinic anhydride 
• 108-24-7 acetic anhydride 
• 101469-91-4 (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 617-48-1 malic acid 
• 24766-96-9 3-acetoxy-2,5-dioxo-tetrahydrofuran 
• 129823-21-8 3-acetoxy-1-benzyl-2,5-pyrrolidinedione 
• 85319-64-8 L-acetoxysuccinic acid 
• 97-67-6 (S)-Malic acid 

Downstream Products

• 129823-21-8 (S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione 
• 165657-63-6 (3R)-1-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 132917-66-9 acetic acid (2S,3S)-1-benzyl-2-hydroxy-5-oxo-pyrrolidin-3-yl ester 
• 188295-12-7 (S)-1-Benzyl-5-ethoxy-4-hydroxy-pyrrolidin-2-one 
• 199103-42-9 Acetic acid (S)-1-benzyl-2-ethoxy-5-oxo-pyrrolidin-3-yl ester 
• 174684-58-3 (S)-1-benzyl-3-(tert-butyldimethylsilyloxy)pyrrolidine-2,5-dione 
• 74880-19-6 methyl-(2S,4R)-4-amino-1-benzylpyrrolidine 
• 253608-05-8 Acetic acid (S)-1-benzyl-2-hydroxy-5-oxo-pyrrolidin-3-yl ester 
• 141737-56-6 Acetic acid (2R,3S)-1-benzyl-2-hydroxy-5-oxo-pyrrolidin-3-yl ester 
• 132549-39-4 Acetic acid (S)-1-benzyl-2-hydroxy-2-(2-methyl-allyl)-5-oxo-pyrrolidin-3-yl ester 
• 74880-19-6 C₁₂H₁₈N₂ 
• 130781-14-5 Acetic acid (2R,3S)-2-allyl-1-benzyl-5-oxo-pyrrolidin-3-yl ester 
• 130781-14-5 Acetic acid (2R,3R)-2-allyl-1-benzyl-5-oxo-pyrrolidin-3-yl ester 

Relevant articles and documents

Lewis-acid catalyzed N-acyliminium ion cyclodimerization: Synthesis of symmetrical 1,4-dioxanes

The cyclodimerization reaction of N-substituted-5-hydroxy-pyrrolydinones promoted by BF3·Et2O and HCl to obtain symmetrical 1,4-dioxane derivatives was achieved in moderate to good yields, mild conditions, and short reaction times. These transformations render a promising alternative route that provides access to diverse 1,4-dioxane derivatives with a wide structural diversity.

COMPOUNDS INHIBITING LEUCINE-RICH REPEAT KINASE ENZYME ACTIVITY

Disclosed are indazole compounds which are potent inhibitors of LRRK2 kinase and useful in the treatment or prevention of diseases in which LRRK2 kinase is involved. Also disclosed are pharmaceutical compositions in the prevention or treatment of such diseases in which LRRK2 kinase is involved.

3-Hydroxypyrrolidine and (3,4)-dihydroxypyrrolidine derivatives: Inhibition of rat intestinal α-glucosidase

Thirteen pyrrolidine-based iminosugar derivatives have been synthesized and evaluated for inhibition of α-glucosidase from rat intestine. The compounds studied were the non-hydroxy, mono-hydroxy and dihydroxypyrrolidines. All the compounds were N-benzylated apart from one. Four of the compounds had a carbonyl group in the 2,5-position of the pyrrolidine ring. The most promising iminosugar was the trans-3,4-dihydroxypyrrolidine 5 giving an IC50 of 2.97 ± 0.046 and a KI of 1.18 mM. Kinetic studies showed that the inhibition was of the mixed type, but predominantly competitive for all the compounds tested. Toxicological assay results showed that the compounds have low toxicity. Docking studies showed that all the compounds occupy the same region as the DNJ inhibitor on the enzyme binding site with the most active compounds establishing similar interactions with key residues. Our studies suggest that a rotation of ～90° of some compounds inside the binding pocket is responsible for the complete loss of inhibitory activity. Despite the fact that activity was found only in the mM range, these compounds have served as simple molecular tools for probing the structural features of the enzyme, so that inhibition can be improved in further studies.