(S)-3-(1-Oxo-5-(piperazin-1-yl)isoindolin-2-yl)piperidine-2,6-dione benzenesulfonate
[CAS# 2229714-16-1]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: (S)-3-(1-Oxo-5-(piperazin-1-yl)isoindolin-2-yl)piperidine-2,6-dione benzenesulfonate
• Molecular Formula: C₂₃H₂₆N₄O₆S
• Molecular Weight: 486.54
• CAS Registry Number: 2229714-16-1
• SMILES: C1CC(=O)NC(=O)[C@H]1N2CC3=C(C2=O)C=CC(=C3)N4CCNCC4.C1=CC=C(C=C1)S(=O)(=O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Discovory and Applicatios

(S)-3-(1-Oxo-5-(piperazin-1-yl)isoindolin-2-yl)piperidine-2,6-dione benzenesulfonate is a structurally complex organic compound that integrates multiple functional groups, including an isoindolinone core, a piperidine-2,6-dione system, and a piperazine moiety. The benzenesulfonate salt form influences the compound’s solubility, stability, and potential interactions in various chemical and biological environments. Due to its structural components, this compound has attracted attention in medicinal and organic chemistry, particularly in drug discovery and pharmaceutical formulation.

The discovery of such compounds is linked to advancements in synthetic organic chemistry, particularly in the development of heterocyclic frameworks with bioactive potential. Isoindolinone derivatives have been widely studied due to their presence in various biologically active molecules, including anticancer, anti-inflammatory, and neuroactive agents. The incorporation of a piperazine ring further enhances its potential pharmacological properties, as piperazine derivatives are commonly found in a broad range of therapeutic drugs, including antipsychotics, antihistamines, and antibiotics.

The synthesis of (S)-3-(1-Oxo-5-(piperazin-1-yl)isoindolin-2-yl)piperidine-2,6-dione benzenesulfonate likely involves multi-step synthetic procedures, including selective cyclization, functional group modifications, and salt formation. The stereochemistry of the compound plays a crucial role in its biological activity, as enantiomers can exhibit distinct interactions with biological targets. The benzenesulfonate counterion is often introduced in the final stages of synthesis to improve the solubility and bioavailability of the compound, which is critical for pharmaceutical applications.

One of the primary applications of this compound is in pharmaceutical development. Isoindolinone and piperidine-dione derivatives are known for their roles in modulating various biological pathways, including protein-protein interactions and enzymatic inhibition. These structural motifs have been investigated in the design of inhibitors for key enzymes implicated in diseases such as cancer, neurodegenerative disorders, and autoimmune conditions. The presence of a piperazine group contributes to enhanced binding affinity to biological targets, as piperazine-containing drugs are often optimized for interactions with receptors and enzymes.

The benzenesulfonate salt form is particularly relevant in drug formulation, as it can enhance the compound’s pharmacokinetic properties. Salts of active pharmaceutical ingredients (APIs) are frequently used to optimize drug solubility, absorption, and stability. The choice of benzenesulfonate as a counterion suggests a consideration of these factors, potentially improving the compound’s performance in biological systems.

Beyond pharmaceuticals, heterocyclic compounds with similar frameworks have applications in organic synthesis and material sciences. Piperazine-containing molecules serve as key intermediates in the synthesis of more complex organic molecules and are widely used in medicinal chemistry research. Additionally, the chemical stability of isoindolinone and piperidine-dione structures makes them useful in various research settings, including the development of novel materials and chemical probes for biological studies.

Analytical techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and X-ray crystallography play essential roles in characterizing the structure and purity of this compound. These methods help confirm stereochemistry, detect impurities, and evaluate the physicochemical properties necessary for further development. Computational chemistry and molecular docking studies may also be employed to predict its interactions with biological targets, guiding the optimization of its structure for specific therapeutic applications.

As research in synthetic and medicinal chemistry progresses, compounds like (S)-3-(1-Oxo-5-(piperazin-1-yl)isoindolin-2-yl)piperidine-2,6-dione benzenesulfonate continue to be explored for their potential in drug discovery and beyond. The integration of heterocyclic motifs, optimized physicochemical properties, and synthetic accessibility makes such compounds valuable in both academic and industrial research. Advances in synthetic methodologies, coupled with high-throughput screening techniques, may further refine the applications and effectiveness of this molecule in future pharmaceutical and chemical developments.

References

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