8-Bromo-3-methyl-3,7-dihydropurine-2,6-dione
[CAS# 93703-24-3]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 8-Bromo-3-methyl-3,7-dihydropurine-2,6-dione
• Synonyms: 8-Bromo-3-methylxanthine
• Molecular Formula: C₆H₅BrN₄O₂
• Molecular Weight: 245.03
• CAS Registry Number: 93703-24-3
• EC Number: 819-117-0
• SMILES: CN1C2=C(C(=O)NC1=O)NC(=N2)Br

Properties

• Density: 1.974
• Melting point: 320-327 °C

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

8-Bromo-3-methyl-3,7-dihydropurine-2,6-dione, a significant chemical compound, has garnered interest due to its unique structural and functional properties. This compound belongs to the class of purine derivatives, characterized by its bromine substitution and methyl group modifications. The discovery and applications of 8-Bromo-3-methyl-3,7-dihydropurine-2,6-dione highlight its relevance in various fields of chemistry and pharmaceuticals.

The discovery of 8-Bromo-3-methyl-3,7-dihydropurine-2,6-dione can be traced back to research aimed at expanding the library of purine-based compounds. Purine derivatives are known for their biological significance, as they play crucial roles in nucleic acid chemistry and enzyme inhibition. The specific structural modifications in 8-Bromo-3-methyl-3,7-dihydropurine-2,6-dione, including the introduction of a bromine atom and a methyl group, provide unique reactivity patterns and potential applications in drug development.

One of the primary applications of 8-Bromo-3-methyl-3,7-dihydropurine-2,6-dione is in the synthesis of novel pharmaceuticals. The compound's ability to act as a building block for more complex molecules makes it valuable in medicinal chemistry. Its structure facilitates the development of purine analogs that can be used as inhibitors or modulators of various biological targets. For instance, derivatives of this compound are explored for their potential as antiviral and anticancer agents.

In addition to its pharmaceutical applications, 8-Bromo-3-methyl-3,7-dihydropurine-2,6-dione is used in chemical research for exploring new reaction mechanisms and developing synthetic methodologies. The bromine substituent introduces an electrophilic center, making the compound useful in cross-coupling reactions and other transformations. This versatility in synthetic applications allows researchers to create a diverse array of compounds with potential uses in materials science and chemical biology.

The compound also has implications in biochemical research. Its structural similarity to natural purines enables studies on enzyme interactions and nucleic acid binding. By examining how 8-Bromo-3-methyl-3,7-dihydropurine-2,6-dione and its derivatives interact with biological molecules, scientists can gain insights into fundamental biochemical processes and develop new therapeutic strategies.

In summary, 8-Bromo-3-methyl-3,7-dihydropurine-2,6-dione is a valuable compound in the realm of chemical and pharmaceutical research. Its unique structural features make it a useful tool for synthesizing novel drugs and exploring new chemical reactions. The compound's applications extend to both practical and theoretical aspects of chemistry, highlighting its significance in advancing scientific knowledge and developing new technologies.

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

2018. Synthesis and Antidepressant Properties of 3-Methyl-7-(1,1-Dioxothietan-3-YL)-8-Cyclohexylamino-1-Ethyl-1H-Purine-2,6(3H,7H)-Dione. Pharmaceutical Chemistry Journal, 51(12).
DOI: 10.1007/s11094-018-1738-0

2013. Synthesis and Physicochemical and Biological Properties of Heteroannelated 3-Methylxanthine Derivatives. Chemistry of Natural Compounds, 49(5).
DOI: 10.1007/s10600-013-0771-1