673485-72-8

Basic information

• Product Name: 2,6-Piperidinedione,3-amino-,(3R)-(9CI)
• Synonyms: 2,6-Piperidinedione,3-amino-,(3R)-(9CI);(R)-3-Amino-piperidine-2,6-dione
• CAS NO: 673485-72-8
• Molecular Formula: C5H8N2O2
• Molecular Weight: 128.13
• Product Categories: AMINEPRIMARY
• Mol File: 673485-72-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,6-Piperidinedione,3-amino-,(3R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Piperidinedione,3-amino-,(3R)-(9CI)(673485-72-8)
• EPA Substance Registry System: 2,6-Piperidinedione,3-amino-,(3R)-(9CI)(673485-72-8)

Safety Data

• Hazardous Substances Data: 673485-72-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Piperidinedione,3-amino, (3R)-(9CI) serves as an intermediate in the production of various drugs, playing a crucial role in the synthesis of pharmaceuticals. Its specific stereochemistry contributes to the development of drugs with targeted biological activities.
Used in Organic Synthesis:
In the realm of organic synthesis, 2,6-Piperidinedione,3-amino, (3R)-(9CI) acts as a building block, facilitating the creation of a wide range of organic compounds. Its unique structure and functional groups make it a valuable component in the synthesis of complex organic molecules for various applications.

Upstream product

• 179915-11-8 (R)-3-N-Cbz-amino-2,6-dioxopiperidine 
• 56-85-9 L-glutamine 
• 22785-43-9 (S)-benzyl (2,6-dioxopiperidin-3-yl)carbamate 
• 13726-85-7 Boc-Gln-OH 
• 151367-92-9 L-tert-butyl N-[2,6-dioxohexahydro-3-pyridinyl] Carbamate 
• 24666-55-5 3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine 
• 56-85-9 GLUTAMINE 
• 1218991-05-9 glutamine methyl ester 
• 2650-64-8 Cbz-L-Gln 
• 4976-88-9 (S)-methyl 5-amino-2-(tert-butoxycarbonylamino)-5-oxopentanoate 
• 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

• 1314881-81-6 padanamide B 
• 55003-81-1 2-(2,6-dioxo-3-piperidinyl)-5-nitro-1H-isoindole-1,3(2H)-dione 
• 50-35-1 thalidomide 
• 444289-22-9 N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)benzamide 

Relevant articles and documents

Preparation method of lenalidomide

The invention provides a preparation method of lenalidomide. The preparation method of the lenalidomide comprises the steps of preparing an intermediate 2-halogen methyl-3 methyl nitrobenzoate and anintermediate 3-amino piperidine-2,6-diketone, and preparing the lenalidomide by using the two intermediates. The preparation method of the lenalidomide is simple in steps, high in yield, low in cost,and beneficial to industrial production.

Preparation method of deuterated intermediate

The present invention provides a preparation method of a deuterated intermediate. The deuterated intermediate has a structure shown by a formula I; the preparation method comprises the following steps: amino groups in a raw material A and an aldehyde grou

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.

Lenalidomide and lenalidomide intermediate preparation method

A lenalidomide and lenalidomide intermediate preparation method includes the following four steps: (1) intramolecular ring-closure of N-Boc-glutamine methyl ester (I) in the presence of a condensing agent and a catalyst to obtain 3-Boc-imino-piperidine-2,6-dione (II); (2) deprotection reaction of the compound (II) obtained by the step (1) to obtain 3-(N-Boc-imino) - piperidine-2,6-dione (III); (3) condensation reaction of the compound (III) obtained by the step (2) and 2-bromomethyl-3-nitrobenzoate (IV) to obtain 3-( 7-nitro-3-oxo-1H-isoindole-2-yl)-piperidine-2,6-dione (V); and (4) nitro group reduction reaction of the compound (V) obtained by the step (3) to obtain lenalidomide (VI); and a synthetic route is shown in the specification.

Total synthesis of padanamides A and B

The first total syntheses of padanamides A and B have been achieved, unambiguously confirming their structures. The Royal Society of Chemistry.

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.

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.

5H-THIOENO(3,4-c)PYRROLE-4,6-DIONE DERIVATIVES AND THEIR USE AS TUMOR NECROSIS FACTOR INHIBITORS

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5H-THIENO [3,4-c]PYRROLE-4, 6-DIONE DERIVATIVES AGAINST CELL RELEASING TUMOR NECROSIS FACTOR

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THALIDOMIDE ANALOGS

Thalidomide analogs that modulate tumor necrosis factor alpha (TNF-α) activity and angiogenesis are disclosed. In particularly disclosed embodiments, the thalidomide analogs are isosteric sulfur-containing analogs. Also disclosed are methods of treating a subject with the analogs.