8-Benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolin-2-one
[CAS# 530084-79-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Quinoline compound
• Name: 8-Benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolin-2-one
• Synonyms: (R)-8-Benzyloxy-5-(2-bromo-1-hydroxyethyl)carbostyril; 5-(2-Bromo-(R)-1-hydroxyethyl)-8-benzyloxy-2(1H)-quinolinone; 8-(Benzyloxy)-5-((1R)-2-bromo-1-hydroxyethyl)quinolin-2(1H)-one
• Molecular Formula: C₁₈H₁₆BrNO₃
• Molecular Weight: 374.23
• CAS Registry Number: 530084-79-8
• EC Number: 610-932-5
• SMILES: C1=CC=C(C=C1)COC2=C3C(=C(C=C2)[C@H](CBr)O)C=CC(=O)N3

Properties

• Solubility: Practically insoluble (0.022 g/L) (25 °C), Calc.^*
• Density: 1.490±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.649, Calc.^*
• Boiling Point: 595.8±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 314.1±30.1 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Risk Statements: H317-H318-H341-H412
• Safety Statements: P203-P261-P264+P265-P272-P273-P280-P302+P352-P305+P354+P338-P317-P318-P321-P333+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Germ cell mutagenicity	Muta.	2	H341
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Serious eye damage	Eye Dam.	1	H318

Discovery and Applications

8-Benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolin-2-one is a complex chemical compound that has gained attention in the field of medicinal chemistry due to its potential biological activity. It belongs to a class of quinoline derivatives, which are known for their diverse pharmacological properties, including anticancer, antimicrobial, and anti-inflammatory activities. The structure of this compound includes a quinolinone backbone, which is modified with a benzyloxy group and a bromo-hydroxyethyl side chain. This combination of functional groups enhances the compound's ability to interact with biological targets, making it an interesting candidate for drug development.

The discovery of 8-Benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolin-2-one is part of the ongoing exploration of quinoline derivatives for their therapeutic potential. Quinoline and its derivatives have been well-studied due to their broad spectrum of activity against various diseases. The incorporation of a bromo group into the quinoline structure, particularly at the 5-position, is significant as it can alter the compound's reactivity and binding affinity with specific targets, such as enzymes and receptors involved in disease processes. The addition of a benzyloxy group at the 8-position further modifies the compound’s lipophilicity and enhances its ability to penetrate cell membranes, which is a key factor in drug efficacy.

In terms of application, 8-Benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolin-2-one has been primarily investigated for its potential as an anticancer agent. Quinoline derivatives have been shown to interfere with cancer cell growth by inhibiting key enzymes involved in DNA replication and cell division. The bromo-hydroxyethyl side chain may contribute to the compound's ability to form covalent bonds with certain enzymes, leading to their inhibition. This mechanism of action makes this compound a promising candidate for targeted cancer therapy. Additionally, the quinoline core structure is known to interact with metal ions, which could also play a role in its antitumor activity by disrupting metal-dependent processes within cancer cells.

Another area where 8-Benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolin-2-one shows promise is in the treatment of microbial infections. Quinoline-based compounds, including those with bromine substitutions, have demonstrated antimicrobial activity against a wide range of pathogens, including bacteria and fungi. The unique structural features of this compound, particularly the bromo-hydroxyethyl moiety, may contribute to its ability to inhibit the growth of microbial organisms by disrupting cell wall synthesis or other essential cellular processes.

The synthesis of 8-Benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolin-2-one typically involves the selective functionalization of the quinoline core. The bromo-hydroxyethyl group is introduced via a bromination reaction, followed by hydroxyethylation to position the functional group at the desired location on the quinoline ring. The benzyloxy group is typically introduced through a nucleophilic substitution reaction, where the benzyloxy group is added to the quinoline ring at the 8-position. The final product is purified through crystallization or chromatography to yield a high-quality compound suitable for biological testing.

In conclusion, 8-Benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolin-2-one is a promising chemical substance with significant potential for the development of new therapeutic agents, particularly in the areas of cancer treatment and antimicrobial therapy. Its unique combination of functional groups makes it an interesting molecule for further research and development in drug discovery.

References

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