202271-89-4

Basic information

• Product Name: (-)-4-Amino-2-[2,6-dioxopiperidin-3(S)-yl]-1,2-dihydroisoindole-1,3-dione
• Synonyms: ENMD-0995; S-3APG
• CAS NO: 202271-89-4
• Molecular Formula: C₁₃H₁₁N₃O₄
• Molecular Weight: 273.25032
• Mol File: 202271-89-4.mol
• Article Data: 53

Chemical Properties

• CAS DataBase Reference: (-)-4-Amino-2-[2,6-dioxopiperidin-3(S)-yl]-1,2-dihydroisoindole-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-4-Amino-2-[2,6-dioxopiperidin-3(S)-yl]-1,2-dihydroisoindole-1,3-dione(202271-89-4)
• EPA Substance Registry System: (-)-4-Amino-2-[2,6-dioxopiperidin-3(S)-yl]-1,2-dihydroisoindole-1,3-dione(202271-89-4)

Safety Data

• Hazardous Substances Data: 202271-89-4(Hazardous Substances Data)

Usage

Description

(-)-4-Amino-2-[2,6-dioxopiperidin-3(S)-yl]-1,2-dihydroisoindole-1,3-dione, also known as (S)-Pomalidomide, is a stereoisomer of Pomalidomide (P688205). It is a potent inhibitor of TNF-α production and possesses anti-inflammatory and antitumor properties. (-)-4-Amino-2-[2,6-dioxopiperidin-3(S)-yl]-1,2-dihydroisoindole-1,3-dione is a promising pharmaceutical candidate for various applications due to its ability to modulate immune responses and exhibit therapeutic effects against certain types of cancer.

Uses

Used in Pharmaceutical Industry:
(-)-4-Amino-2-[2,6-dioxopiperidin-3(S)-yl]-1,2-dihydroisoindole-1,3-dione is used as an anti-inflammatory agent for its ability to inhibit TNF-α production, which is a key mediator of inflammation. This property makes it a valuable compound in the development of treatments for various inflammatory conditions.
Used in Oncology:
(-)-4-Amino-2-[2,6-dioxopiperidin-3(S)-yl]-1,2-dihydroisoindole-1,3-dione is used as an antitumor agent for its therapeutic effects against multiple myeloma, a type of blood cancer. It is employed in the treatment of this disease due to its ability to modulate immune responses and target cancer cells, leading to the inhibition of tumor growth and progression.
Used in Drug Development:
(-)-4-Amino-2-[2,6-dioxopiperidin-3(S)-yl]-1,2-dihydroisoindole-1,3-dione is used as a lead compound in the development of new drugs targeting inflammation and cancer. Its unique properties and mechanisms of action make it a valuable starting point for the design and synthesis of novel therapeutic agents with improved efficacy and reduced side effects.

Upstream product

• 202271-81-6 (R)-2-(2,6-dioxo(3-piperidyl))-4-nitroisoindoline-1,3-dione 
• 603-62-3 4-nitro-1H-isoindole-1,3(2H)-dione 
• 190910-88-4 ethyl 4-nitro-1,3-dioxoisoindoline-2-carboxylate 
• 918314-40-6 N-(3-nitrophthaloyl)-D-glutamine 
• 918314-39-3 t-butyl N-(3-nitrophthaloyl)-D-glutamine 
• 19171-18-7 4-NT 
• 2650-64-8 Cbz-L-Gln 
• 22785-43-9 (S)-benzyl (2,6-dioxopiperidin-3-yl)carbamate 
• 118061-00-0 (3S)-3-aminopiperidine-2,6-dione hydrobromide 
• 202271-78-1 (S)-2-(2,6-dioxo(3-piperidyl))-4-nitroisoindoline-1,3-dione 
• 918314-36-0 N-(3-nitrophthaloyl)-L-glutamine 
• 918314-38-2 t-butyl N-(3-nitrophthaloyl)-L-glutamine 
• 641-70-3 3-nitrophthalic acid anhydride 
• 603-11-2 3-nitrophthalic acid 

Downstream Products

• 444287-84-7 2‐chloro‐N‐(2‐(2,6‐dioxopiperidin‐3‐yl)‐1,3‐dioxoisoindolin‐4‐yl)acetamide 

Relevant articles and documents

Rational Design and Synthesis of HSF1-PROTACs for Anticancer Drug Development

PROTACs employ the proteosome-mediated proteolysis via E3 ligase and recruit the natural protein degradation machinery to selectively degrade the cancerous proteins. Herein, we have designed and synthesized heterobifunctional small molecules that consist of different linkers tethering KRIBB11, a HSF1 inhibitor, with pomalidomide, a commonly used E3 ligase ligand for anticancer drug development.

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.

PHOTO INDUCED CONTROL OF PROTEIN DESTRUCTION

By hijacking endogenous E3 ligase to degrade protein targets via the ubiquitin-proteasome system, PROTACs (PRoteolysis TArgeting Chimeras) provide a new strategy to inhibit protein targets that were previously regarded as undruggable. The compounds described herein comprise a photolabile group on PROTACs, enabling the degradation of protein targets in a spatiotemporally controlled manner. By adding a photolabile caging group on ubiquitin recruiting moieties, light-inducible protein degradation was acheived. These opto-PROTACs display no activity in the dark, while restricted degradation can be induced at a specific time and rate by UVA-irradiation. Accordingly, these compounds provide light-controlled PROTACs and methods of using such compounds.