3-(5-Bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione
[CAS# 1010100-26-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate
• Name: 3-(5-Bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione
• Synonyms: 3-(6-bromo-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione
• Molecular Formula: C₁₃H₁₁BrN₂O₃
• Molecular Weight: 323.14
• CAS Registry Number: 1010100-26-1
• EC Number: 861-824-1
• SMILES: C1CC(=O)NC(=O)C1N2CC3=C(C2=O)C=CC(=C3)Br

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.651, Calc.^*
• Boiling Point: 587.6±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 309.1±30.1 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

3-(5-Bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione is a noteworthy compound in medicinal chemistry and drug design. It is also known as bromopiperidone and has a complex structure with a piperidine ring fused to a bromine-substituted isoindolinone, giving it unique chemical and biological properties.

The discovery of 3-(5-Bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione can be traced back to the ongoing research in the field of heterocyclic chemistry aimed at synthesizing novel compounds with potential therapeutic effects. The compound is characterized by its molecular structure containing a piperidine-2,6-dione core attached to a 5-bromoisoindolinone moiety, demonstrating a perfect fusion of aromatic and cyclic components. The bromine atom increases its reactivity and biological activity, making it an object of interest for various scientific studies.

The synthesis of bromopiperidone involves complex organic reactions, including condensation and bromination processes, reflecting its complex structure. The compound is presented as a crystalline solid with unique chemical reactivity due to the presence of bromine atoms and the conjugated system in its structure. This reactivity can be used to create derivatives with enhanced biological activity.

Bromoperidone has been studied intensively primarily as a scaffold for drug development. Its unique structure serves as a template for the synthesis of analogs and derivatives with enhanced pharmacological properties. Researchers have used it to develop new drugs that target specific biological pathways, particularly in the treatment of cancer and inflammatory diseases.

Studies have shown that derivatives of bromoperidone exhibit promising anticancer activity. These compounds interact with cellular targets and may inhibit cancer cell growth and proliferation. Their ability to induce apoptosis (programmed cell death) in tumor cells highlights their potential as candidates for anticancer therapy.

Bromoperidone derivatives have also been studied for their anti-inflammatory effects. By modulating specific signaling pathways associated with inflammation, these compounds can reduce the production of inflammatory mediators, offering potential therapeutic benefits for inflammatory and autoimmune diseases.

The unique structure of the compound makes it suitable for use as a molecular probe in biochemical studies. It can be labeled with a variety of tags to track and study biological processes at the molecular level. This application is particularly valuable in drug discovery, where understanding the interaction of potential drugs with their targets is crucial.

The structure of bromoperidone facilitates structure-activity relationship (SAR) studies, helping scientists understand how modifications to a molecule affect its biological activity. This knowledge guides the optimization of drug candidates to improve their efficacy and safety.

References

2023. Design, synthesis, and evaluation of BTK-targeting PROTACs with optimized bioavailability in vitro and in vivo. RSC Medicinal Chemistry, 14(8).
DOI: 10.1039/d3md00216k

2022. Protein inhibitor or degrading agent, pharmaceutical composition containing same and pharmaceutical use. WO-2022268229-A1.

2022. Novel bifunctional heterocyclic compound having btk degradation function via ubiquitin proteasome pathway, and use thereof. WO-2022270994-A1.