31804-66-7

Basic information

• Product Name: 6-(2,6-dioxopiperidin-3-yl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione
• Synonyms: 6-(2,6-Dioxopiperidin-3-yl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione;3-{5,7-dioxo-5H,6H,7H-pyrrolo[3,4-b]pyridin-6-yl}piperidine-2,6-dione;5H-Pyrrolo[3,4-b]pyridine-5,7(6H)-dione, 6-(2,6-dioxo-3-piperidinyl)-
• CAS NO: 31804-66-7
• Molecular Formula: C₁₂H₉N₃O₄
• Molecular Weight: 259.2176
• Mol File: 31804-66-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 545.7°C at 760 mmHg
• Flash Point: 283.9°C
• Density: 1.571g/cm³
• Vapor Pressure: 5.75E-12mmHg at 25°C
• Refractive Index: 1.653
• PKA: 10.51±0.40(Predicted)
• CAS DataBase Reference: 6-(2,6-dioxopiperidin-3-yl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(2,6-dioxopiperidin-3-yl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione(31804-66-7)
• EPA Substance Registry System: 6-(2,6-dioxopiperidin-3-yl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione(31804-66-7)

Safety Data

• Hazardous Substances Data: 31804-66-7(Hazardous Substances Data)

Usage

Description

3-{5,7-dioxo-5H,6H,7H-pyrrolo[3,4-b]pyridin-6-yl}piperidine-2,6-dione is a thalidomide analog that can be useful in PROTAC research.

Upstream product

• 85535-45-1 5-amino-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid 
• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 
• 31140-42-8 (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester 
• 590365-46-1 (RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate 

Relevant articles and documents

Synthesis of alpha-(quinolinimido)-glutarimide (author's transl)

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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.

Imides

Cyclic imides are inhibitors of tumor necrosis factor α and can be used to combat cachexia, endotoxic shock, and retrovirus replication. A typical embodiment is 2-(2,6-dioxo-3-piperidinyl)-4-azaisoindoline-1,3-dione.