8-Bromo-7-(2-butynyl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione
[CAS# 666816-98-4]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleotides and their analogues
• Name: 8-Bromo-7-(2-butynyl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione
• Synonyms: 3-Methyl-7-(2-butyn-1-yl)-8-bromoxanthine
• Molecular Formula: C₁₀H₉BrN₄O₂
• Molecular Weight: 297.11
• CAS Registry Number: 666816-98-4
• EC Number: 613-975-8
• SMILES: CC#CCN1C2=C(N=C1Br)N(C(=O)NC2=O)C

Properties

• Density: 1.71

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovery and Applications

8-Bromo-7-(2-butynyl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione is a complex chemical compound with notable significance in organic synthesis and medicinal chemistry. This molecule is an example of a purine derivative, which features a bromine atom and a butynyl group attached to the purine ring structure. The synthesis and applications of this compound highlight its versatility and importance in various chemical and pharmaceutical contexts.

The discovery of 8-Bromo-7-(2-butynyl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione emerged from research focused on modifying purine structures to explore new chemical and biological properties. The synthesis of this compound typically involves halogenation and alkyne coupling reactions, which are designed to introduce the bromine and butynyl groups into the purine ring. This process is significant for expanding the chemical diversity of purine derivatives and investigating their potential applications.

In organic synthesis, 8-Bromo-7-(2-butynyl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione is utilized as an intermediate in the preparation of more complex molecules. Its unique structure, featuring both a halogen and an alkyne group, allows for further chemical modifications that can lead to the development of new compounds with specific properties. For instance, the bromine atom can be used in cross-coupling reactions, while the butynyl group can participate in additional reactions such as cycloadditions or functional group transformations.

Pharmaceutical research has shown interest in 8-Bromo-7-(2-butynyl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione due to its potential biological activity. The purine ring system is a core structure in many biologically active molecules, including nucleic acids and various drugs. Modifying this ring with different functional groups can yield compounds with unique pharmacological properties. The bromine and butynyl substituents may enhance the compound’s interactions with biological targets or influence its pharmacokinetic and pharmacodynamic properties. Thus, this compound could serve as a lead structure for developing new drugs or therapeutic agents.

Additionally, the compound has applications in materials science. Its chemical structure enables it to be incorporated into polymer matrices or used as a building block for creating functionalized materials. The ability to modify the purine ring with different substituents opens up opportunities for designing materials with specific electronic, optical, or mechanical properties. These materials can be used in various applications, including electronics, sensors, and coatings.

In summary, 8-Bromo-7-(2-butynyl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione is a valuable chemical compound with diverse applications in organic synthesis, pharmaceuticals, and materials science. Its unique structure allows for various chemical modifications and potential uses, underscoring its significance in advancing both chemical and biomedical research.

References

2020. Design, synthesis and biological evaluation of novel 1,2,3-triazole-based xanthine derivatives as DPP-4 inhibitors. Journal of Chemical Sciences, 132(1).
DOI: 10.1007/s12039-020-1760-0