191732-76-0

Basic information

• Product Name: 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
• Synonyms: 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione;1H-Isoindole-1,3(2H)-dione, 5-amino-2-(2,6-dioxo-3-piperidinyl)-;Pomalidomide Impurity F
• CAS NO: 191732-76-0
• Molecular Formula: C₁₃H₁₁N₃O₄
• Molecular Weight: 273.24414
• EINECS: -0
• Mol File: 191732-76-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 603.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.570±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Aqueous Base (Slightly), DMSO (Slightly, Sonicated)
• PKA: 10.83±0.40(Predicted)
• CAS DataBase Reference: 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione(191732-76-0)
• EPA Substance Registry System: 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione(191732-76-0)

Safety Data

• Hazardous Substances Data: 191732-76-0(Hazardous Substances Data)

Usage

Description

5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione is a thalidomide analog, which is a type of chemical compound that has been found to be useful in the field of protein degradation research, specifically in the development of proteolysis-targeting chimeras (PROTACs). These chimeras are designed to selectively degrade target proteins within cells, which can be a promising approach for the treatment of various diseases.

Uses

Used in Pharmaceutical Industry:
5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione is used as a research compound for the development of novel protein degradation therapies. Its application in this field is due to its structural similarity to thalidomide, which allows it to be utilized in the design and synthesis of new PROTACs that can selectively target and degrade specific proteins involved in disease pathways.
Used in Research and Development:
In the context of research and development, 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione serves as a valuable tool for scientists to study the mechanisms of protein degradation and to identify potential therapeutic targets for various diseases. Its use in this application is driven by the need to develop innovative and effective treatments that can address unmet medical needs.
Used in Drug Discovery:
5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione is also used in drug discovery efforts, where it can be employed to identify new lead compounds with potential therapeutic applications. Its use in this area is based on its ability to modulate protein degradation pathways, which can provide insights into the development of new drugs that can target specific proteins for degradation, thereby offering a new approach to treating diseases.

Upstream product

• 31140-42-8 (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester 
• 85535-45-1 5-amino-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid 
• 24666-55-5 3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine 
• 24666-56-6 rac-α-aminoglutarimide hydrochloride 
• 2650-64-8 Cbz-L-Gln 
• 55003-81-1 2-(2,6-dioxo-3-piperidinyl)-5-nitro-1H-isoindole-1,3(2H)-dione 
• 5466-84-2 4-nitrophthalic anhydride 

Relevant articles and documents

Facile synthesis of an azido-labeled thalidomide analogue

(Matrix presented) A five-step synthesis of an azido-thalidomide analogue is presented. The sequence requires cheap and readily available starting materials and reagents, and only two steps require purification. Additionally, the azido-labeled analogue possesses activity comparable to that of thalidomide in inhibiting the proliferation of human microvascular endothelial cells, thus providing impetus for its use as a potential photoaffinity label of thalidomide.

Compound for targeted degradation of adhesion spot kinase and application thereof (by machine translation)

The invention belongs to the technical field of medicines, and provides a compound as shown in general formula (I) and geometric isomers or pharmaceutically acceptable salts, hydrates, solvates, prodrugs and a preparation method thereof. The compound has good degradation activity on the adhesion spot kinase (FAK). The compounds, and geometric isomers or pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof are as shown in the general formula I, wherein Y, L, X, Z, R1 What is claimed is: the claims and the description. (by machine translation)

Efficient Synthesis of Immunomodulatory Drug Analogues Enables Exploration of Structure–Degradation Relationships

The immunomodulatory drugs (IMiDs) thalidomide, pomalidomide, and lenalidomide have been approved for the treatment of multiple myeloma for many years. Recently, their use as E3 ligase recruiting elements for small-molecule-induced protein degradation has led to a resurgence in interest in IMiD synthesis and functionalization. Traditional IMiD synthesis follows a stepwise route with multiple purification steps. Herein we describe a novel one-pot synthesis without purification that provides rapid access to a multitude of IMiD analogues. Binding studies with the IMiD target protein cereblon (CRBN) reveals a narrow structure–activity relationship with only a few compounds showing sub-micromolar binding affinity in the range of pomalidomide and lenalidomide. However, anti-proliferative activity as well as Aiolos degradation could be identified for two IMiD analogues. This study provides useful insight into the structure–degradation relationships for molecules of this type as well as a rapid and robust method for IMiD synthesis.