64567-60-8

Basic information

• Product Name: 2-(2,6-dioxopiperidin-3-yl)-5-hydroxy-1H-isoindole-1,3(2H)-dione
• Synonyms: 1H-isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-5-hydroxy-
• CAS NO: 64567-60-8
• Molecular Formula: C₁₃H₁₀N₂O₅
• Molecular Weight: 274.2289
• Mol File: 64567-60-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 600°C at 760 mmHg
• Flash Point: 316.7°C
• Density: 1.611g/cm³
• Vapor Pressure: 5.46E-15mmHg at 25°C
• Refractive Index: 1.679
• CAS DataBase Reference: 2-(2,6-dioxopiperidin-3-yl)-5-hydroxy-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,6-dioxopiperidin-3-yl)-5-hydroxy-1H-isoindole-1,3(2H)-dione(64567-60-8)
• EPA Substance Registry System: 2-(2,6-dioxopiperidin-3-yl)-5-hydroxy-1H-isoindole-1,3(2H)-dione(64567-60-8)

Safety Data

• Hazardous Substances Data: 64567-60-8(Hazardous Substances Data)

Usage

General Description

2-(2,6-dioxopiperidin-3-yl)-5-hydroxy-1H-isoindole-1,3(2H)-dione, also known as Bz-423, is a synthetic chemical compound that has shown potential as an anti-inflammatory and immunosuppressive agent. It has been studied for its ability to inhibit the production of pro-inflammatory cytokines and to induce apoptosis of activated T-cells, making it a possible candidate for the treatment of autoimmune diseases and transplant rejection. Bz-423 has also been investigated for its potential anti-cancer properties due to its ability to induce programmed cell death in cancer cells. Further research is ongoing to explore the therapeutic applications of this compound and to better understand its mechanism of action.

Upstream product

• 27550-59-0 4-hydroxyphthalic anhydride 
• 31140-42-8 (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester 
• 24666-56-6 rac-α-aminoglutarimide hydrochloride 
• 590365-46-1 (RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate 

Relevant articles and documents

COMPOUNDS AND USES THEREOF

The present disclosure features compounds and methods useful for the treatment of BAF complex-related disorders.

Substituted quinoline-8-carbonitrile derivatives having androgen receptor degradation activity and uses thereof

The present disclosure relates to novel compounds, pharmaceutical compositions containing such compounds, and their use in prevention and treatment of cancer and related diseases and conditions. In some embodiments, the compounds disclosed herein exhibit androgen receptor degradation activity.

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.