5-(2R)-2-Oxiranyl-8-benzyloxy-2(1H)-quinolinone
[CAS# 173140-90-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Quinoline compound
• Name: 5-(2R)-2-Oxiranyl-8-benzyloxy-2(1H)-quinolinone
• Synonyms: PubChem
• Molecular Formula: C₁₈H₁₅NO₃
• Molecular Weight: 293.32
• CAS Registry Number: 173140-90-4
• EC Number: 478-690-1
• SMILES: C1[C@H](O1)C2=C3C=CC(=O)NC3=C(C=C2)OCC4=CC=CC=C4

Properties

• Density: 1.298±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.643, Calc.^*
• Boiling Point: 556.0±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 290.0±30.1 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1	H317

Discovory and Applicatios

5-(2R)-2-Oxiranyl-8-benzyloxy-2(1H)-quinolinone is a chemical compound that has attracted interest in medicinal chemistry due to its potential pharmacological activities. Quinolinone derivatives, including this compound, are known for their diverse biological properties, making them promising candidates for the development of new therapeutic agents. The compound belongs to a class of chemicals that combine an oxirane (epoxide) group with a quinolinone backbone, a structure that enhances the chemical’s reactivity and biological activity.

The discovery of 5-(2R)-2-oxiranyl-8-benzyloxy-2(1H)-quinolinone can be traced to ongoing efforts to develop novel molecules with the potential to treat a variety of diseases, including cancers and neurological disorders. The unique structure of this compound, with its oxirane group and quinolinone core, makes it a potentially valuable scaffold for the design of molecules that can interact with biological targets in specific ways.

The epoxide group in 5-(2R)-2-oxiranyl-8-benzyloxy-2(1H)-quinolinone is a reactive functional group known for its ability to form covalent bonds with nucleophilic sites on proteins, enzymes, and other biomolecules. This reactivity is often utilized in drug design to create compounds that can modulate enzyme activity or other cellular functions. Quinolinone derivatives, in particular, have been studied for their ability to inhibit enzymes involved in cancer progression, inflammation, and other pathological conditions.

5-(2R)-2-Oxiranyl-8-benzyloxy-2(1H)-quinolinone’s benzyloxy group also contributes to its potential bioactivity. The presence of a benzyloxy moiety enhances the compound’s lipophilicity, which may improve its ability to cross biological membranes and reach target tissues. This feature makes it an interesting candidate for drug design, as lipophilic compounds are often better absorbed and more effective in vivo.

In terms of applications, 5-(2R)-2-oxiranyl-8-benzyloxy-2(1H)-quinolinone is primarily under investigation for its potential as an anticancer and neuroprotective agent. Preliminary studies suggest that the compound may possess properties that allow it to inhibit the growth of cancer cells by interfering with cellular signaling pathways or inducing apoptosis (programmed cell death) in tumor cells. Its potential neuroprotective properties also make it a candidate for research into treatments for neurodegenerative diseases, although more studies are required to confirm these effects.

The compound has been studied in vitro for its biological activity, and research is ongoing to understand its full range of pharmacological effects. The combination of the quinolinone structure, epoxide functionality, and benzyloxy group gives 5-(2R)-2-oxiranyl-8-benzyloxy-2(1H)-quinolinone the potential to be developed into a therapeutic agent with broad applications.

In conclusion, 5-(2R)-2-oxiranyl-8-benzyloxy-2(1H)-quinolinone is a promising compound with potential applications in cancer therapy and neuroprotection. Its unique molecular structure and reactivity make it an attractive candidate for further research and development in drug discovery.