26166-92-7

Basic information

• Product Name: 5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione
• Synonyms: 5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione
• CAS NO: 26166-92-7
• Molecular Weight: 337.129
• Mol File: 26166-92-7.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione(26166-92-7)
• EPA Substance Registry System: 5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione(26166-92-7)

Safety Data

• Hazardous Substances Data: 26166-92-7(Hazardous Substances Data)

Usage

Description

5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione is a complex chemical compound characterized by the presence of a bromine atom, a piperidin-3-yl group, and an isoindole-1,3-dione moiety. This unique molecular structure endows it with potential applications across various fields, such as pharmaceuticals, agrochemicals, and materials science. Its functional groups and structural features make it a promising candidate for the development of new molecules with specific properties and functions.

Uses

Used in Pharmaceutical Industry:
5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione is used as a building block for the synthesis of new pharmaceutical compounds due to its unique structure and functional groups. It can contribute to the development of innovative drugs with specific therapeutic properties and functions.
Used in Agrochemical Industry:
In the agrochemical field, 5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione is used as a starting material for the creation of novel agrochemicals. Its structural features and functional groups can be leveraged to design molecules with targeted effects on pests or crops, potentially leading to more effective and environmentally friendly products.
Used in Materials Science:
5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione is utilized in materials science for the development of new materials with specific properties. Its unique molecular structure and functional groups can be employed to create materials with tailored characteristics, such as improved mechanical strength, thermal stability, or electrical conductivity, depending on the application.
Research and Development:
The potential uses and properties of 5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione are currently being explored through ongoing research and development efforts. 5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione holds promise for various applications, and further investigation into its properties and behavior in different contexts could lead to a better understanding of its potential benefits and uses across multiple industries.

Upstream product

• 28418-88-4 3-iodophthalic anhydride 
• 590365-46-1 (RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate 
• 86-90-8 4-bromophthalic anhydride 
• 2353-44-8 (+/-)-α-aminoglutarimide 

Downstream Products

• 1216805-53-6 (RS)-2-(2,6-dioxopiperidin-3-yl)-5-(4-hydroxyphenyl)-isoindoline-1,3-dione 
• 1216805-57-0 (RS)-2-(2,6-dioxopiperidin-3-yl)-5-(4-isopropoxyphenyl)-isoindoline-1,3-dione 
• 1216805-28-5 (RS)-2-(2,6-dioxopiperidin-3-yl)-5-(4-isobutylphenyl)isoindoline-1,3-dione 
• 1216805-51-4 (RS)-2-(2,6-dioxopiperidin-3-yl)-5-p-tolylisoindole-1,3-dione 
• 1216805-25-2 (RS)-5-(4-acetylphenyl)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 
• 1216805-54-7 (RS)-4-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)benzamide 
• 1216805-49-0 (RS)-2-(2,6-dioxopiperidin-3-yl)-5-phenylisoindole-1,3-dione 
• 2154356-63-3 2-(2,6-dioxopiperidin-3-yl)-5-ethynylisoindoline-1,3-dione 
• 2222114-64-7 tert‐butyl 4‐[2‐(2,6‐dioxopiperidin‐1‐id‐3‐yl)‐1,3‐dioxo‐iso‐indolin‐5‐yl]‐piperazine‐1‐carboxylate 

Relevant articles and documents

First orally bioavailable prodrug of proteolysis targeting chimera (PROTAC) degrades cyclin-dependent kinases 2/4/6 in vivo

A growing number of reports suggested that the inhibitor targeting cyclin-dependent kinases (CDK) 2/4/6 can act as a more feasible chemotherapy strategy. In the present paper, a novel PROTAC molecule was developed based on the structure of Ribociclib's derivative. In malignant melanoma cells, the degrader can not only degrade CDK 2/4/6 simultaneously and effectively, but also remarkably induce cell cycle arrest and apoptosis of melanoma cells. Moreover, PROTAC molecules with CRBN ligands always have poor oral bioavailability. We developed the orally bioavailable prodrug for the first time. It would provide general solution for oral administration of the PROTAC molecules, derived from CRBN ligands, for animal test conveniently.

In pursuit of a selective hepatocellular carcinoma therapeutic agent: Novel thalidomide derivatives with antiproliferative, antimigratory and STAT3 inhibitory properties

Advanced stage liver cancer is predominantly treated with the multi-kinase inhibitor sorafenib; however, this therapeutic agent lacks selectivity in its cytotoxic actions and is associated with poor survival outcomes. Herein we report the design and preparation of several thalidomide derivatives, including a variety of novel thioether-containing forms that are especially rare in the literature. Importantly, two of the derivatives described are potent antiproliferative agents with dose-dependent selectivity for tumorigenic liver progenitor cells (LPC) growth inhibition (up to 36% increase in doubling time at 10 μM) over non-tumorigenic cells (no effect at 10 μM). Furthermore, these putative anti-liver cancer agents were also found to be potent inhibitors of tumorigenic LPC migration. This report also describes these derivatives’ effects on several key signalling pathways in our novel liver cell lines by immunofluorescence and AlphaLISA assays. Aryl thioether derivative 7f significantly reduced STAT3 phosphorylation (23%) and its nuclear localisation (16%) at 10 μM in tumorigenic LPCs, implicating the IL-6/JAK/STAT3 axis is central in the mode of action of our derivatives.

BIFUNCTIONAL DEGRADERS OF HEMATOPOIETIC PROGENITOR KINASE AND THERAPEUTIC USES THEREOF

The present disclosure provides bifunctional compounds as HPK1 degraders via ubiquitin proteosome pathway, and method for treating diseases modulated by HPK1.