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Terpyridine

Catalog Number: BT-288869

CAS Number: 1148-79-4

Molecular Formula: C15H11N3

Molecular Weight: 233.27 g/mol

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Product Introduction

Description

Terpyridine is a heterocyclic compound that contains three pyridine rings. It is a versatile ligand that has been extensively studied for its potential applications in various fields, including medical, environmental, and industrial research. The unique chemical structure of terpyridine allows it to form stable complexes with metal ions, making it a valuable tool in coordination chemistry.

Properties

CAS Number

1148-79-4

Product Name

Terpyridine

IUPAC Name

2,6-dipyridin-2-ylpyridine

Molecular Formula

C15H11N3

Molecular Weight

233.27 g/mol

InChI

InChI=1S/C15H11N3/c1-3-10-16-12(6-1)14-8-5-9-15(18-14)13-7-2-4-11-17-13/h1-11H

InChI Key

DRGAZIDRYFYHIJ-UHFFFAOYSA-N

SMILES

C1=CC=NC(=C1)C2=NC(=CC=C2)C3=CC=CC=N3

Synonyms

2,2',2''-terpyridine
2,2',2''-terpyridine diperchlorate
2,2',2''-tripyridine

Canonical SMILES

C1=CC=NC(=C1)C2=NC(=CC=C2)C3=CC=CC=N3

Method of Synthesis or Extraction

Terpyridine can be synthesized using various methods, including the Pinner reaction, the Skraup reaction, and the Chichibabin reaction. The Pinner reaction involves the reaction of pyridine with an alkyl halide in the presence of an acid catalyst. The Skraup reaction involves the condensation of aniline with glycerol and sulfuric acid, followed by oxidation with nitric acid. The Chichibabin reaction involves the reaction of pyridine with sodium amide in liquid ammonia. The efficiency and yield of each method depend on the starting materials, reaction conditions, and purification methods used. The Pinner reaction is the most commonly used method for the synthesis of terpyridine, with a yield of up to 80%. However, this method requires the use of toxic and corrosive reagents, making it environmentally hazardous. The Skraup reaction has a lower yield but is considered safer and more environmentally friendly. The Chichibabin reaction is the least efficient method, with a yield of only 20%, but it is the most environmentally friendly method.

Chemical Structure and Biological Activity

The chemical structure of terpyridine consists of three pyridine rings connected by two carbon-carbon bonds. The nitrogen atoms in the pyridine rings can coordinate with metal ions, forming stable complexes. Terpyridine and its derivatives have been shown to exhibit a wide range of biological activities, including antimicrobial, antitumor, and antiviral activities. The mechanism of action of terpyridine is based on its ability to bind to metal ions, which can affect various biological processes, such as DNA replication and protein synthesis. Terpyridine has been shown to target various biological molecules, including enzymes, receptors, and transporters. The bioactivity and potency of terpyridine depend on the metal ion it coordinates with and the specific biological target.

Biological Effects

Terpyridine has been shown to have both therapeutic and toxic effects on cells. Its ability to bind to metal ions can affect cell function and signal transduction, leading to changes in gene expression and cell proliferation. Terpyridine and its derivatives have been investigated for their potential use in cancer therapy, as they can induce apoptosis and inhibit tumor growth. However, terpyridine can also have toxic effects on cells, depending on the concentration and duration of exposure. High concentrations of terpyridine can cause DNA damage and cell death, making it important to consider the potential therapeutic and toxic effects when using terpyridine in research.

Applications

Terpyridine has numerous applications in medical, environmental, and industrial research. In medical research, terpyridine and its derivatives have been investigated for their potential role in drug development. They have been shown to enhance the activity of existing drugs and to have potential as novel therapeutics. Clinical trials have been conducted to evaluate the safety and efficacy of terpyridine-based drugs, with promising results. However, further research is needed to fully understand the potential benefits and side effects of terpyridine-based drugs. In environmental research, terpyridine has been used to study the effects of metal ions on ecosystems. It has also been investigated for its potential role in pollution management, as it can bind to metal ions and prevent their release into the environment. In industrial research, terpyridine has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations are important when using terpyridine in industrial applications, as it can be toxic if not handled properly.

Future Perspectives and Challenges

Despite the potential applications of terpyridine, there are still limitations in its use and study. One of the main challenges is the toxicity of terpyridine, which can limit its use in certain applications. Another challenge is the lack of understanding of the specific biological targets of terpyridine and its derivatives. Future research should focus on identifying these targets and understanding the mechanisms of action of terpyridine. Possible solutions and improvements include the development of safer and more efficient synthesis methods, the identification of novel biological targets, and the optimization of terpyridine-based drugs for clinical use. The future trends and prospects in the application of terpyridine in scientific research are promising, with the potential for new discoveries and innovations in various fields.
Conclusion:
Terpyridine is a versatile ligand that has numerous potential applications in various fields, including medical, environmental, and industrial research. The methods of synthesis or extraction, chemical structure, biological activity, biological effects, applications, future perspectives, and challenges associated with terpyridine have been discussed in this paper. Further research is needed to fully understand the potential benefits and limitations of terpyridine and its derivatives.

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