2353-44-8

Basic information

• Product Name: 3-aminopiperidine-2,6-dione
• Synonyms: 3-aminopiperidine-2,6-dione;2,6-Piperidinedione, 3-amino-;3-aminopiperidine-2,6-quinone;3-azanylpiperidine-2,6-dione;alpha-Aminoglutarimide;Glutamimide;3-Amino-2,6-piperidinedione;pyroglutamine
• CAS NO: 2353-44-8
• Molecular Formula: C₅H₈N₂O₂
• Molecular Weight: 128.13
• EINECS: 1312995-182-4
• Mol File: 2353-44-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 142-143℃
• Boiling Point: 334.5°Cat760mmHg
• Flash Point: 156.1°C
• Appearance: /
• Density: 1.243g/cm³
• Vapor Pressure: 0.000128mmHg at 25°C
• Refractive Index: 1.498
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 11.15±0.40(Predicted)
• CAS DataBase Reference: 3-aminopiperidine-2,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-aminopiperidine-2,6-dione(2353-44-8)
• EPA Substance Registry System: 3-aminopiperidine-2,6-dione(2353-44-8)

Safety Data

• Hazardous Substances Data: 2353-44-8(Hazardous Substances Data)

Usage

Description

3-aminopiperidine-2,6-dione is a dicarboximide compound that features a piperidine-2,6-dione structure with an amino group substitution at the 3-position. This organic compound plays a significant role in pharmaceutical research and development.

Uses

Used in Pharmaceutical Research:
3-aminopiperidine-2,6-dione serves as a key intermediate in the study of the hydrolytic degradation and primary metabolic pathway of thalidomide. Thalidomide, a sedative drug, is historically known for its use in treating morning sickness but has been associated with severe birth defects when taken during pregnancy.
In the context of pharmaceutical research, understanding the metabolic pathways and degradation processes of drugs like thalidomide is crucial for assessing their safety, efficacy, and potential side effects. The use of 3-aminopiperidine-2,6-dione in such studies aids in the development of safer and more effective medications, as well as in the improvement of drug delivery systems and formulations.

InChI:InChI=1/C5H8N2O2/c6-3-1-2-4(8)7-5(3)9/h3H,1-2,6H2,(H,7,8,9)

Upstream product

• 31140-42-8 (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester 
• 24666-55-5 3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine 
• 4976-88-9 (S)-methyl 5-amino-2-(tert-butoxycarbonylamino)-5-oxopentanoate 
• 13726-85-7 Boc-Gln-OH 
• 56-85-9 GLUTAMINE 
• 1218991-05-9 glutamine methyl ester 
• 2650-64-8 Cbz-L-Gln 
• 120341-33-5 1-[(tert-butoxy)-carbonyl-amino]propane-1,3-dicarboxylic acid 

Downstream Products

• 351432-17-2 3-(benzylamino)piperidine-2,6-dione 
• 55003-81-1 2-(2,6-dioxo-3-piperidinyl)-5-nitro-1H-isoindole-1,3(2H)-dione 
• 19171-18-7 4-NT 
• 1026993-00-9 3-(4-oxo-4H-thieno[3,4-c]pyrrol-5(6H)-yl)piperidine-2,6-dione 
• 827026-45-9 3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione 
• 1547162-84-4 2-(2,6-dioxopiperidin-3-yl)-6-isopropoxy-4-nitroisoindoline-1,3-dione 
• 50-35-1 thalidomide 
• 444289-22-9 N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)benzamide 

Relevant articles and documents

Inhibition of angiogenesis by THAM-derived cotelomers endowed with thalidomide moieties

The synthesis of a tris(hydroxymethyl)acrylamidomethane (THAM)-derived cotelomer endowed with thalidomide units and a preliminary assessment of its biological activity are described. 4-Carboxy thalidomide and 4-(N-acryloyl) lysine thalidomide derivatives were prepared. The polymerization of these compounds with THAM in the presence of octanethiol as transfer reagent provided a water-soluble telomer bearing several thalidomide units. The ability of this telomer to inhibit angiogenesis in a mouse model of corneal neovascularization was compared to 4-carboxy thalidomide and thalidomide. A significant inhibition in area of neovascularization stimulated by a bFGF pellet was observed only in the mice treated with the telomer.

Design, synthesis and biological evaluation of Lenalidomide derivatives as tumor angiogenesis inhibitor

Lenalidomide is a type of immunomodulatory agent with anti-tumor activity by mainly expressed in the anti-angiogenesis. In order to enhance the pharmacological activity of Lenalidomide, a series of Lenalidomide derivatives were designed as tumor angiogenesis inhibitors. The potential anti-angiogenesis targets of Lenalidomide derivatives were virtual screened on Auto-Dock 4.0 by using reverse docking method. The six target proteins, such as vascular endothelial growth factor receptor, epidermal growth factor receptor, fibroblast growth factor receptor, BCR-ABL tyrosine kinase, p38 mitogen activated protein kinase and metal protein kinase, were chosen as the targets. The Lenalidomide derivatives were synthesized by alkylated, acylated or sulfonylated Lenalidomide and verified by the 1H NMR, 13C NMR and LC–MS. Their anti-cancer activities were detected by using CCK-8 in the esophageal carcinoma cell line EC9706. The results indicate that the inhibitory activities of Lenalidomide derivatives were higher than that of Lenalidomide.

Preliminary biological evaluations of new thalidomide analogues for multiple sclerosis application

The present work deals with the synthesis of a new series of thalidomide derivatives for therapeutic applications. These compounds were evaluated in vitro on a human endothelial cell line EA.hy926 for their antiproliferative potential and in vivo on an experimental animal multiple sclerosis model called EAE as angiogenesis inhibitors. The preliminary results obtained on EAE assays seem to validate that anti-angiogenesis compounds could be promising tools for the treatment of MS.