Production Method 1

155057-97-9

909649-12-3

Reaction Conditions

1.1 Solvents: Phosphorus oxychloride ;  28 h, 100 °C
1.2 Reagents: Sodium bicarbonate Solvents: Dichloromethane ,  Water ;  rt

Reference

Ready access to 7,8-dihydro- and 1,2,3,4-tetrahydro-1,6-naphthyridin-5(6H)-ones from simple pyridine precursors

Showalter, H. D. Hollis, Journal of Heterocyclic Chemistry, 2006, 43(5), 1311-1317

8-Bromo-5-chloro-1,6-naphthyridine Raw materials

• 8-Bromo-1,6-naphthyridin-5(6H)-one

8-Bromo-5-chloro-1,6-naphthyridine Preparation Products

• 8-Bromo-5-chloro-1,6-naphthyridine (909649-12-3)

• 1. Excellent electrochemical performance of LiFe0.4Mn0.6PO4 microspheres produced using a double carbon coating process?
  Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying Chen J. Mater. Chem. A, 2014,2, 18831-18837
• 2. Emerging 2D hybrid nanomaterials: towards enhanced sensitive and selective conductometric gas sensors at room temperature
  Hanie Hashtroudi,Ian D. R. Mackinnon J. Mater. Chem. C, 2020,8, 13108-13126
• 3. Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR?
  Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing Xia Nanoscale, 2020,12, 20456-20466
• 4. Emerging investigator series: kinetics of diopside reactivity for carbon mineralization in mafic–ultramafic rocks
  BrianaAguila,LandonHardee,H.ToddSchaef,SiavashZare,MohammadJavadAbdolhosseiniQomi,JarrodV.Crum,JadeE.HollimanJr.,ElenaTajueloRodriguez,LawrenceM.Anovitz,KevinM.Rosso,QuinR.S.Miller
• 5. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755

Recent Advances in the Application of 8-Bromo-5-chloro-1,6-naphthyridine (CAS: 909649-12-3) in Chemical Biology and Pharmaceutical Research

The compound 8-Bromo-5-chloro-1,6-naphthyridine (CAS: 909649-12-3) has emerged as a pivotal scaffold in chemical biology and pharmaceutical research due to its unique structural and electronic properties. Recent studies have highlighted its potential as a versatile intermediate in the synthesis of bioactive molecules, particularly in the development of kinase inhibitors and other targeted therapies. This research brief consolidates the latest findings on this compound, focusing on its synthetic applications, biological activities, and mechanistic insights.

One of the most significant advancements in the use of 8-Bromo-5-chloro-1,6-naphthyridine is its role in the synthesis of novel kinase inhibitors. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its utility as a key intermediate in the development of selective inhibitors for the JAK2 kinase, a target implicated in myeloproliferative disorders. The study reported that derivatives of this compound exhibited nanomolar potency and high selectivity, underscoring its potential in precision medicine approaches.

In addition to its applications in kinase inhibitor development, 8-Bromo-5-chloro-1,6-naphthyridine has also been explored as a building block for fluorescent probes. Researchers have leveraged its electron-deficient naphthyridine core to design probes for detecting reactive oxygen species (ROS) in cellular environments. A recent publication in Chemical Communications detailed the synthesis of a ROS-sensitive probe that exhibited high sensitivity and specificity, enabling real-time monitoring of oxidative stress in live cells.

Mechanistic studies have further elucidated the interactions of 8-Bromo-5-chloro-1,6-naphthyridine with biological targets. Computational modeling and X-ray crystallography have revealed that the bromo and chloro substituents play critical roles in binding affinity and selectivity. These insights are informing the rational design of next-generation therapeutics, with several candidates currently in preclinical development.

The pharmaceutical industry has also taken note of the commercial potential of 8-Bromo-5-chloro-1,6-naphthyridine. Recent patent filings indicate a growing interest in its use as a core structure for antiviral agents, particularly against RNA viruses. Preliminary data suggest that naphthyridine-based compounds exhibit broad-spectrum activity, making them promising candidates for further investigation.

Despite these promising developments, challenges remain in optimizing the pharmacokinetic properties of 8-Bromo-5-chloro-1,6-naphthyridine derivatives. Issues such as solubility and metabolic stability are areas of active research, with several groups exploring prodrug strategies and formulation technologies to overcome these limitations.

In conclusion, 8-Bromo-5-chloro-1,6-naphthyridine (CAS: 909649-12-3) represents a versatile and valuable scaffold in chemical biology and drug discovery. Its applications span from kinase inhibitors to fluorescent probes, with ongoing research continuing to uncover new opportunities. As the field advances, this compound is poised to play an increasingly important role in the development of innovative therapeutics and diagnostic tools.

• 947238-42-8(3-Bromo-4-chloro-1H-pyrrolo[3,2-c]pyridine)
• 1000341-61-6(3-Bromo-6-chloro-1H-pyrrolo[3,2-c]pyridine)
• 163485-86-7(8-Bromo-2-chloroquinoline)
• 101870-60-4(3-Bromo-2-chloroquinoline)
• 207461-11-8(1,10-Phenanthroline, 8-bromo-2-chloro-)
• 1211588-58-7(3-Bromo-5-chloro-1,6-naphthyridine)
• 1000342-04-0(7-Bromo-4-chloro-1H-pyrrolo[3,2-c]pyridine)
• 38052-80-1( )
• 406204-90-8(6-bromo-2,4-dichloro-quinoline)
• 406204-86-2(8-bromo-2,4-dichloro-quinoline)