4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine - 918801-05-5

4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine

Catalog Number: EVT-1665706
CAS Number: 918801-05-5
Molecular Formula: C24H20N2
Molecular Weight: 336.4 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'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine, also known as TPD, is a compound that has gained significant attention in scientific research due to its potential applications in various fields. TPD is a polycyclic aromatic hydrocarbon that contains two pyridine rings and a phenyl ring, connected by two ethynyl groups.
Applications in Various Fields
In medical research, 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine has been studied for its potential role in drug development. For example, 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine has been found to enhance the activity of certain chemotherapeutic agents, potentially improving their efficacy. 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine has also been studied in clinical trials for the treatment of cancer, with promising results. In environmental research, 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine has been studied for its effects on ecosystems and its potential role in pollution management. 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine has been found to have a low toxicity to aquatic organisms, making it a potential candidate for use in pollution management. In industrial research, 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine has been used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations should be taken into account when using 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine in industrial settings.

Properties

CAS Number

918801-05-5

Product Name

4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine

IUPAC Name

4-[2-[2,3,5,6-tetramethyl-4-(2-pyridin-4-ylethynyl)phenyl]ethynyl]pyridine

Molecular Formula

C24H20N2

Molecular Weight

336.4 g/mol

InChI

InChI=1S/C24H20N2/c1-17-18(2)24(8-6-22-11-15-26-16-12-22)20(4)19(3)23(17)7-5-21-9-13-25-14-10-21/h9-16H,1-4H3

InChI Key

IDJIUEOEJRHYRR-UHFFFAOYSA-N

SMILES

CC1=C(C(=C(C(=C1C#CC2=CC=NC=C2)C)C)C#CC3=CC=NC=C3)C

Canonical SMILES

CC1=C(C(=C(C(=C1C#CC2=CC=NC=C2)C)C)C#CC3=CC=NC=C3)C
Method of Synthesis or Extraction
There are several methods for synthesizing 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine, including the Sonogashira coupling reaction, the Suzuki coupling reaction, and the Glaser coupling reaction. The Sonogashira coupling reaction involves the reaction of 2-bromo-5,6-dimethylpyridine with trimethylsilylacetylene in the presence of a palladium catalyst. The Suzuki coupling reaction involves the reaction of 2-bromo-5,6-dimethylpyridine with phenylboronic acid in the presence of a palladium catalyst. The Glaser coupling reaction involves the reaction of 2-bromo-5,6-dimethylpyridine with copper(I) oxide in the presence of oxygen. The efficiency and yield of each method vary, with the Sonogashira coupling reaction being the most efficient and yielding the highest amount of 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine. However, the environmental and safety considerations of each method should also be taken into account, as some methods may involve toxic or hazardous reagents.
Chemical Structure and Biological Activity
4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine has been found to exhibit biological activity, particularly in its ability to inhibit the activity of protein kinases. Protein kinases are enzymes that play a crucial role in cell signaling and are involved in various cellular processes, including cell growth, differentiation, and apoptosis. 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine has been shown to inhibit the activity of several protein kinases, including c-Src, Abl, and EGFR. This inhibition is thought to occur through the binding of 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine to the ATP-binding site of the kinase, preventing the kinase from phosphorylating its substrate. 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine has also been found to exhibit anti-inflammatory and anti-tumor activity.
Biological Effects
The inhibition of protein kinases by 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine has been shown to have several biological effects on cell function and signal transduction. For example, the inhibition of c-Src by 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine has been found to reduce the migration and invasion of cancer cells, while the inhibition of EGFR has been found to reduce the proliferation of cancer cells. 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine has also been found to induce apoptosis in cancer cells, potentially making it a useful therapeutic agent for the treatment of cancer. However, 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine may also have potential toxic effects, as the inhibition of protein kinases may disrupt normal cellular processes.
Future Perspectives and Challenges
Despite the potential applications of 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine in various fields, there are still limitations in its use and study. For example, the mechanism of action of 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine is not fully understood, and further research is needed to elucidate its biological effects. Additionally, the potential toxic effects of 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine should be further studied to ensure its safety for use in various applications. Possible solutions and improvements include the development of more efficient and environmentally friendly methods for synthesizing 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine, as well as the development of more specific and potent inhibitors of protein kinases. Future trends and prospects in the application of 4,4'-[(2,3,5,6-Tetramethyl-1,4-phenylene)di(ethyne-2,1-diyl)]dipyridine in scientific research include its potential use in combination therapies for cancer treatment and its potential role in the development of new drugs for the treatment of other diseases.

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