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

Uses

3-Amino-piperidine-2,6-dione is used for studies on the hydrolytic degradation and primary metabolic pathway of thalidomide in animals and human liver microsomes. Thalidomide is a sedative drug used to treat morning sickness.

Definition

ChEBI: A dicarboximide that is piperidine-2,6-dione substituted at position 3 by an amino group.

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

Upstream product

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

Downstream Products

• 351432-17-2 3-(benzylamino)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.

PYRROLINE-2-ONE DERIVATIVES AGAINST CELL RELEASING TUMOR NECROSIS FACTOR, PREPARATION METHODS AND USES THEREOF

Compounds represented by Formula (I) or Formula (II), their pharmaceutically acceptable salts or hydrates wherein A, B and E independently represent CH2 or CO; D represents S, NH, or NC1-6 alkylhydrocarbyl; R represents H or R3, R1 represents H, or 1-2 same or different occurrences of radical(s) selected from the group consisting of F, Cl, Br, C1-4 alkylhydrocarbyl, OH, OC1-4 alkylhydrocarbyl, NO2, NHC(O)C1-4 alkylhydrocarbyl, NH2, NH(C1-4 alkylhydrocarbyl), N(C1-4 alkylhydrocarbyl)2; and R2 represents F, CF3, H or C1-4 alkylhydrocarbyl; are active inhibitors of TNFα. Provided are also preparation methods and uses thereof.