55003-81-1

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-5-nitro-
• Synonyms: 2-(2,6-dioxo-piperidin-3-yl)-5-nitro-isoindole-1,3-dione;N-(2,6-dioxopiperidin-3-yl)-4-nitrophthalimide;1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)-5-nitroisoindoline;2-(2,6-dioxo-3-piperidinyl)-5-nitro-1H-isoindole-1,3(2H)-dione;4-nitrothalidomide;1H-Isoindole-1,3(2H)-dione,2-(2,6-dioxo-3-piperidinyl)-5-nitro;2-(4'-Nitro-phthalimido)-glutarimid
• CAS NO: 55003-81-1
• Molecular Formula: C13H9N3O6
• Molecular Weight: 303.22700
• Mol File: 55003-81-1.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-5-nitro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-5-nitro-(55003-81-1)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-5-nitro-(55003-81-1)

Safety Data

• Hazardous Substances Data: 55003-81-1(Hazardous Substances Data)

Usage

General Description

1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-5-nitro- is a chemical compound with the molecular formula C13H10N4O6. It is a nitro-substituted derivative of isoindolin-1-one, which is commonly used in the synthesis of pharmaceuticals and dyes. 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-5-nitro- has potential biological activities and is being researched for its anti-inflammatory and anticancer properties. As a nitro compound, it may also have applications as a nitric oxide donor or as a precursor to other nitrogen-containing compounds. However,

Upstream product

• 5466-84-2 4-nitrophthalic anhydride 
• 24666-56-6 rac-α-aminoglutarimide hydrochloride 
• 2353-44-8 (+/-)-α-aminoglutarimide 
• 13726-85-7 Boc-Gln-OH 
• 89-40-7 4-nitrophthalimide 
• 590365-46-1 aminoglutarimide trifluoroacetate 
• 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 
• 2650-64-8 Cbz-L-Gln 
• 590365-46-1 (RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate 

Downstream Products

• 191732-76-0 2-(2,6-dioxo-3-piperidinyl)-5-amino-1H-isoindole-1,3(2H)-dione 

Relevant articles and documents

Influence of Linker Attachment Points on the Stability and Neosubstrate Degradation of Cereblon Ligands

Proteolysis targeting chimeras (PROTACs) hijacking the cereblon (CRBN) E3 ubiquitin ligase have emerged as a novel paradigm in drug development. Herein we found that linker attachment points of CRBN ligands highly affect their aqueous stability and neosubstrate degradation features. This work provides a blueprint for the assembly of future heterodimeric CRBN-based degraders with tailored properties.

De-novo design of cereblon (CRBN) effectors guided by natural hydrolysis products of thalidomide derivatives

Targeted protein degradation via cereblon (CRBN), a substrate receptor of an E3 ubiquitin ligase complex, is an increasingly important strategy in various clinical settings, in which the substrate specificity of CRBN is altered via the binding of small-molecule effectors. To date, such effectors are derived from thalidomide and confer a broad substrate spectrum that is far from being fully characterized. Here, we employed a rational and modular approach to design novel and minimalistic CRBN effectors. In this approach, we took advantage of the binding modes of hydrolyzed metabolites of several thalidomide-derived effectors, which we elucidated via crystallography. These yielded key insights for the optimization of the minimal core binding moiety and its linkage to a chemical moiety that imparts substrate specificity. Based on this scaffold, we present a first active de-novo CRBN effector that is able to degrade the neo-substrate IKZF3 in the cell culture.

TUNABLE ENDOGENOUS PROTEIN DEGRADATION WITH HETEROBIFUNCTIONAL COMPOUNDS

The present invention provides a means to modulate gene expression in vivo in a manner that avoids problems associated with CRISPR endogenous protein knock-out or knock-in strategies and strategies that provide for correction, or alteration, of single nucleotides. The invention includes inserting into the genome a nucleotide encoding a heterobifunctional compound targeting protein (dTAG) in-frame with the nucleotide sequence of a gene encoding an endogenously expressed protein of interest which, upon expression, produces an endogenous protein-dTAG hybrid protein. This allows for targeted protein degradation of the dTAG and the fused endogenous protein using a heterobifunctional compound.