26166-92-7

Usage

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

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

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 academic research and scientific papers

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 vitro and in vivo degradation of programmed cell death ligand 1 (PD-L1) by a proteolysis targeting chimera (PROTAC)

Immunotherapy via immune checkpoints blockade has aroused the attention of researchers worldwide. Inhibition of the programmed cell death-1 (PD-1)/programmed cell death-ligand 1 (PD-L1) interaction has been one of the most promising immunotherapy strategies. Several neutralizing antibodies targeting this interaction have been developed, which have already achieved considerable clinical success. Additionally, numerous pharmaceutical companies have been committed to develop small molecules which could block the interaction between PD-1 and PD-L1. In this study, a novel PROTAC molecule 21a was developed, and effectively induced the degradation of PD-L1 protein in various malignant cells in a proteasome-dependent manner. Moreover, compound 21a could significantly reduce PD-L1 protein levels of MC-38 cancer cells in vivo, by which promoted the invasion of CD8+ T cells and inhibited the growth of MC-38 in vivo. This PROTAC molecule could be used as a novel and alternative strategy for cancer immunotherapy.

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.

Proteolysis targeting chimera and application thereof

The invention provides a proteolysis targeting chimera and application thereof. According to a technical scheme in the invention, a novel PROTAC degradation agent compound 21a is developed on the basis of a BMS-37 small molecule. The novel PROTAC degradation agent compound 21a is an example of degrading membrane proteins on the basis of a ligand binding to the extracellular domain of a PD-L1 protein, and can effectively degrade PD-L1 in various malignant tumor cells. In-vivo research results show that after treatment with the compound 21a, the compound 21a can significantly reduce the level of the PD-L1 in tumors, promote infiltration of CD8T cells and significantly inhibit growth of mouse colorectal cancer MC-38 cells. The PROTAC molecule is expected to be one of novel and alternative strategies for cancer immunotherapy.

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.

PROTEIN-TARGETING COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF, AND THEIR THERAPEUTIC APPLICATIONS

The present disclosure provides compounds, for example, a compound of Formula (I), that modulate a protein function and/or restore protein homeostasis. The disclosure provides a method of modulating a protein-mediated disease, disorder, condition, or response. Compositions, including in combination with other therapeutic agents, are provided.

AMINOAMIDE COMPOUNDS

Compounds with amino amide linkers and pharmaceutical compositions and medicaments comprising such compounds are disclosed. The compounds modulate protein function of 1L-1β, IL-2, IL-6, TNF-α, CK1α, GSPT1, aiolos, ikaros or helios, or combinations thereof. In addition, methods of making such compounds and their uses for treating or ameliorating diseases, disorders, or conditions associated with protein malfunction, such as cancer, are provided.

Compounds for targeted ubiquitination and degradation of GSK-3beta protein and application thereof

The invention discloses compounds shown by a general formula (I) as shown in the specification. The compounds provided by the invention can effectively targetedly degrading GSK-3beta in vivo, and thetechnique can effectively reduce the dosage of administration and time of administration of pharmaceutical molecules to achieve the effect of prolonging PD.