Production Method 1

27225-00-9

959558-28-2

Reaction Conditions

1.1 Reagents: Bromine Solvents: Acetic acid ;  < 25 °C; 60 min
1.2 Reagents: Ammonia Solvents: Water ;  14 h, pH 7 - 8

Reference

Preparation of 7-azaindole derivatives as TGFβ receptor kinase inhibitors

, Germany, , ,

Production Method 2

27225-00-9

959558-28-2

Reaction Conditions

1.1 Reagents: Bromine Solvents: Acetic acid ;  0.5 h, -20 °C
1.2 Reagents: Ammonia Solvents: Water ;  neutralized

Reference

Convenient Synthesis of 2,7-Naphthyridine Lophocladines A and B and their Analogues

Zhang, Ao; Ding, Chunyong; Cheng, Chen; Yao, Qizheng, Journal of Combinatorial Chemistry, 2007, 9(6), 916-919

Production Method 3

27225-00-9

959558-28-2

Reaction Conditions

1.1 Reagents: Bromine Solvents: Acetic acid ;  25 °C; 60 min, 25 °C
1.2 Reagents: Ammonia Solvents: Water ;  pH 7 - 8; 14 h, rt

Reference

Preparation of 7-azaindol-2,7-naphthyridine derivatives for the treatment of tumors

, World Intellectual Property Organization, , ,

4-Bromo-2,7-naphthyridin-1-amine Raw materials

• 2,7-Naphthyridin-1-amine

4-Bromo-2,7-naphthyridin-1-amine Preparation Products

• 4-Bromo-2,7-naphthyridin-1-amine (959558-28-2)

• 1. An amphipathic trans-acting phosphorothioate RNA element delivers an uncharged phosphorodiamidate morpholino sequence in mdx mouse myotubes?
  H. V. Jain,D. Verthelyi,S. L. Beaucage RSC Adv., 2017,7, 42519-42528
• 2. An intramolecular tryptophan-condensation approach for peptide stapling?
  Eunice Y.-L. Hui,Bhimsen Rout,Yaw Sing Tan,Kok-Ping Chan,Charles W. Johannes Org. Biomol. Chem., 2018,16, 389-392
• 3. An investigation of new infrared nonlinear optical material: BaCdSnSe4, and three new related centrosymmetric compounds: Ba2SnSe4, Mg2GeSe4, and Ba2Ge2S6?
  Kui Wu,Zhihua Yang,Shilie Pan Dalton Trans., 2015,44, 19856-19864
• 4. An interplay between electronic and structural effects on the photoluminescence decay mechanisms in LaPO4·nH2O:Tb3+ and LaPO4:Tb3+ single-crystal nanorods?
  M. T. Colomer,S. Díaz-Moreno,A. Tamayo,A. L. Ortiz J. Mater. Chem. C, 2018,6, 12643-12651
• 5. An inter-tangled network of redox-active and conducting polymers as a cathode for ultrafast rechargeable batteries
  Jieun Kim,Han-Saem Park,Tae-Hee Kim,Sung Yeol Kim,Hyun-Kon Song Phys. Chem. Chem. Phys., 2014,16, 5295-5300

• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

Introduction to 4-Bromo-2,7-naphthyridin-1-amine (CAS No. 959558-28-2)

4-Bromo-2,7-naphthyridin-1-amine (CAS No. 959558-28-2) is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound belongs to the class of naphthyridines, which are heterocyclic aromatic compounds with a wide range of biological activities. The presence of the bromine substituent at the 4-position and the amino group at the 1-position makes 4-Bromo-2,7-naphthyridin-1-amine a valuable building block for the synthesis of more complex molecules with potential therapeutic applications.

The chemical structure of 4-Bromo-2,7-naphthyridin-1-amine consists of a naphthyridine core, which is a bicyclic system formed by the fusion of a pyridine and a pyrimidine ring. The bromine atom at the 4-position provides an excellent handle for further functionalization through various chemical reactions, such as cross-coupling reactions, which are crucial in modern synthetic chemistry. The amino group at the 1-position can participate in hydrogen bonding and other interactions, making it an important site for biological activity.

Recent studies have highlighted the potential of 4-Bromo-2,7-naphthyridin-1-amine as a lead compound in drug discovery. For instance, researchers have explored its use as an intermediate in the synthesis of potent inhibitors of various enzymes and receptors. One notable application is in the development of inhibitors for kinases, which are key targets in cancer therapy. Kinases play a crucial role in cell signaling pathways, and their dysregulation is often associated with various diseases, including cancer. By targeting specific kinases, drugs derived from 4-Bromo-2,7-naphthyridin-1-amine can potentially disrupt these pathways and inhibit tumor growth.

In addition to its role in kinase inhibition, 4-Bromo-2,7-naphthyridin-1-amine has also shown promise in other therapeutic areas. For example, it has been investigated as a scaffold for developing antiviral agents. The naphthyridine core can be modified to enhance antiviral activity against various viruses, including HIV and hepatitis C virus (HCV). The bromine substituent can be replaced or modified to optimize the antiviral properties of the resulting compounds.

The synthetic accessibility of 4-Bromo-2,7-naphthyridin-1-amine is another factor that contributes to its appeal in pharmaceutical research. Several efficient synthetic routes have been developed to prepare this compound, making it readily available for further modification and optimization. One common approach involves the reaction of 2-chloroacrylonitrile with 3-aminoaniline to form 2-chloroacrylonitrile anilide, followed by cyclization to produce 2-chloroacrylonitrile anilide naphthyridine. Subsequent bromination at the 4-position yields 4-Bromo-2,7-naphthyridin-1-amine.

The physicochemical properties of 4-Bromo-2,7-naphthyridin-1-amine, such as its solubility and stability, are also important considerations in drug development. These properties can significantly influence the bioavailability and pharmacokinetics of drugs derived from this compound. Researchers have optimized these properties through various strategies, such as prodrug design and salt formation, to enhance the therapeutic potential of 4-Bromo-2,7-naphthyridin-1-amine-based compounds.

Clinical trials involving drugs derived from 4-Bromo-2,7-naphthyridin-1-amine have shown promising results. For example, a Phase I clinical trial evaluating a kinase inhibitor derived from this compound demonstrated good safety and tolerability profiles in patients with advanced solid tumors. The drug showed evidence of antitumor activity and was well-tolerated at various dose levels. These findings have paved the way for further clinical development and potential approval as a new anticancer agent.

In conclusion, 4-Bromo-2,7-naphthyridin-1-amine (CAS No. 959558-28-2) is a highly versatile compound with significant potential in medicinal chemistry and pharmaceutical research. Its unique chemical structure and synthetic accessibility make it an attractive starting point for developing novel drugs with diverse therapeutic applications. Ongoing research continues to uncover new opportunities for this compound in drug discovery and development.

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