N-[(3-Chlorophenyl)methyl]-spiro[piperidine-4,2'(1'H)-quinoxalin]-3'-amine
[CAS# 950455-15-9]

Identification

• Classification: Biochemical >> Inhibitor >> Metabolism >> Ferroptosis inhibitor
• Name: N-[(3-Chlorophenyl)methyl]-spiro[piperidine-4,2'(1'H)-quinoxalin]-3'-amine
• Synonyms: Liproxstatin-1
• Molecular Formula: C₁₉H₂₁ClN₄
• Molecular Weight: 340.85
• CAS Registry Number: 950455-15-9
• SMILES: C1CNCCC12C(=NCC3=CC(=CC=C3)Cl)NC4=CC=CC=C4N2

Properties

• Solubility: Insoluble (3.1E^-3 g/L) (25 °C), Calc.^*, 10 mM in DMSO (Expl.)
• Density: 1.32±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 581.4±50.0 °C 760 mmHg (Calc.)^*
• Flash point: 305.4±30.1 °C (Calc.)^*
• Index of refraction: 1.678 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

N-[(3-Chlorophenyl)methyl]-spiro[piperidine-4,2'(1'H)-quinoxalin]-3'-amine is a synthetic organic compound characterized by a spirocyclic structure linking a piperidine ring and a quinoxaline moiety. The molecule features a chlorophenylmethyl substituent attached to the nitrogen atom, contributing to its chemical specificity and potential biological activity.

The discovery of this compound is rooted in medicinal chemistry efforts aimed at developing new bioactive molecules with potential therapeutic applications. Spirocyclic frameworks, such as the spiro[piperidine-4,2'(1'H)-quinoxalin] core, have attracted considerable attention due to their unique three-dimensional shapes, which often translate into enhanced receptor binding affinity and selectivity. Incorporation of halogenated phenyl groups, like the 3-chlorophenylmethyl substituent, is a common strategy to modulate lipophilicity and metabolic stability.

Research into this class of compounds typically involves structure-activity relationship (SAR) studies to optimize pharmacological profiles. Compounds with similar scaffolds have been investigated for various biological activities, including antimicrobial, anticancer, and central nervous system (CNS) effects. The precise bioactivity of N-[(3-Chlorophenyl)methyl]-spiro[piperidine-4,2'(1'H)-quinoxalin]-3'-amine depends on its interaction with specific biological targets, which may include receptors, enzymes, or ion channels.

Applications of such compounds are predominantly found in drug discovery programs where they serve as lead compounds or intermediates. Their spirocyclic nature contributes to better pharmacokinetic properties, including improved absorption and metabolic resistance, making them attractive candidates for further development. Additionally, the presence of the amine functionality provides a site for further chemical modification, allowing medicinal chemists to tailor the molecule for enhanced efficacy or reduced toxicity.

Due to the structural complexity and potential biological relevance, this compound and its derivatives are subjects of ongoing research to determine their full spectrum of activity and therapeutic potential. However, specific clinical applications or commercial pharmaceutical uses for N-[(3-Chlorophenyl)methyl]-spiro[piperidine-4,2'(1'H)-quinoxalin]-3'-amine have not been widely established or reported in the literature to date.

In summary, N-[(3-Chlorophenyl)methyl]-spiro[piperidine-4,2'(1'H)-quinoxalin]-3'-amine represents a promising synthetic molecule within medicinal chemistry, valued for its spirocyclic architecture and halogenated substituent. Its discovery is linked to drug design efforts focusing on novel scaffolds with potential biological activity, and while its full applications remain under investigation, it serves as a notable example of contemporary compound development aimed at therapeutic innovation.

References

2014. Inactivation of the ferroptosis regulator Gpx4 triggers acute renal failure in mice. Nature Cell Biology, 16(12).
DOI: 10.1038/ncb3064

2022. Liproxstatin-1 induces cell cycle arrest, apoptosis, and caspase-3/GSDME-dependent secondary pyroptosis in K562 cells. International Journal of Oncology, 61(4).
DOI: 10.3892/ijo.2022.5409

2024. Selection of reference genes in liproxstatin-1-treated K562 Leukemia cells via RT-qPCR and RNA sequencing. Molecular Biology Reports, 51(1).
DOI: 10.1007/s11033-023-08912-5