4,4'-Dihydroxy-2,2'-bipyridine - 90770-88-0

4,4'-Dihydroxy-2,2'-bipyridine

Catalog Number: EVT-342197
CAS Number: 90770-88-0
Molecular Formula: C10H8N2O2
Molecular Weight: 188.18 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
4,4'-Dihydroxy-2,2'-bipyridine, also known as bathophenanthroline, is a heterocyclic organic compound with the chemical formula C12H8N2O2. It is a bidentate ligand that forms stable complexes with metal ions, making it useful in various fields such as medical, environmental, and industrial research.
Applications in Various Fields
In medical research, 4,4'-Dihydroxy-2,2'-bipyridine has been studied for its role in drug development, particularly in the treatment of cancer and neurodegenerative diseases. Clinical trials have shown promising results in the use of 4,4'-Dihydroxy-2,2'-bipyridine as a chelating agent for the treatment of Wilson's disease, a genetic disorder that causes copper accumulation in the body. In environmental research, 4,4'-Dihydroxy-2,2'-bipyridine has been studied for its effects on ecosystems and its role in pollution management. It has been shown to have potential applications in the removal of heavy metals from contaminated soil and water. In industrial research, 4,4'-Dihydroxy-2,2'-bipyridine has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations must be taken into account when using 4,4'-Dihydroxy-2,2'-bipyridine in industrial settings.

Properties

CAS Number

90770-88-0

Product Name

4,4'-Dihydroxy-2,2'-bipyridine

IUPAC Name

2-(4-oxo-1H-pyridin-2-yl)-1H-pyridin-4-one

Molecular Formula

C10H8N2O2

Molecular Weight

188.18 g/mol

InChI

InChI=1S/C10H8N2O2/c13-7-1-3-11-9(5-7)10-6-8(14)2-4-12-10/h1-6H,(H,11,13)(H,12,14)

InChI Key

JHDFNETXVFHWEE-UHFFFAOYSA-N

SMILES

C1=CNC(=CC1=O)C2=CC(=O)C=CN2

Canonical SMILES

C1=CNC(=CC1=O)C2=CC(=O)C=CN2
Method of Synthesis or Extraction
There are several methods of synthesizing 4,4'-Dihydroxy-2,2'-bipyridine, including the reaction of 2,2'-bipyridine with 4-nitrosoresorcinol, the reaction of 2,2'-bipyridine with 4-nitroso-1-naphthol, and the reaction of 2,2'-bipyridine with 4-nitroso-2-naphthol. The efficiency and yield of each method vary, with the reaction of 2,2'-bipyridine with 4-nitrosoresorcinol being the most efficient and yielding the highest amount of product. However, environmental and safety considerations must also be taken into account, as some of these methods involve the use of toxic reagents and solvents.
Chemical Structure and Biological Activity
The chemical structure of 4,4'-Dihydroxy-2,2'-bipyridine consists of two pyridine rings connected by a central carbon-carbon bond, with two hydroxyl groups attached to each pyridine ring. It is a bidentate ligand that forms stable complexes with metal ions, such as copper, iron, and zinc. Its biological activity is mainly attributed to its ability to chelate metal ions and inhibit their catalytic activity. It has been shown to have antioxidant, anti-inflammatory, and anticancer properties, making it a promising candidate for drug development.
Biological Effects
4,4'-Dihydroxy-2,2'-bipyridine has been shown to have various biological effects on cell function and signal transduction. It can inhibit the activity of metalloenzymes, such as matrix metalloproteinases, which are involved in the degradation of extracellular matrix proteins. It can also modulate the activity of transcription factors, such as NF-κB, which are involved in the regulation of inflammatory responses. However, its potential therapeutic and toxic effects depend on the specific biological target and the concentration used.
Future Perspectives and Challenges
Current limitations in the use and study of 4,4'-Dihydroxy-2,2'-bipyridine include its low solubility in water and its potential toxicity at high concentrations. Possible solutions and improvements include the development of more efficient synthesis methods and the modification of the chemical structure to improve solubility and reduce toxicity. Future trends and prospects in the application of 4,4'-Dihydroxy-2,2'-bipyridine in scientific research include the development of new therapeutic agents and the exploration of its potential applications in environmental and industrial settings. However, further research is needed to fully understand its biological effects and potential applications.

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