2,6-Dihydroxy-3-methylpurine
[CAS# 1076-22-8]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleotides and their analogues
• Name: 2,6-Dihydroxy-3-methylpurine
• Synonyms: 3-Methylxanthine; 3-Methyl-3,7-dihydro-1H-purine-2,6-dione
• Molecular Formula: C₆H₆N₄O₂
• Molecular Weight: 166.14
• CAS Registry Number: 1076-22-8
• EC Number: 214-058-1
• SMILES: CN1C2=C(C(=O)NC1=O)NC=N2

Properties

• Melting point: >300 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

2,6-Dihydroxy-3-methylpurine is a chemical compound of significant interest in the field of nucleoside and nucleotide chemistry. This compound, a derivative of purine, has attracted attention due to its structural similarity to naturally occurring purines such as adenine and guanine, which are fundamental components of DNA and RNA. The discovery and application of 2,6-Dihydroxy-3-methylpurine have contributed to advancements in medicinal chemistry, particularly in the development of antiviral and anticancer agents.

The initial interest in 2,6-Dihydroxy-3-methylpurine arose from its potential as a nucleobase analog. Researchers hypothesized that modifying the purine ring, specifically by introducing hydroxyl groups at the 2 and 6 positions and a methyl group at the 3 position, could alter the compound's biological activity, making it a candidate for drug development. This modification results in a structure that can mimic or interfere with the function of natural purines in biological systems, potentially leading to the inhibition of key enzymes involved in nucleic acid metabolism.

One of the primary applications of 2,6-Dihydroxy-3-methylpurine is in the development of nucleoside analogs, which are used as antiviral and anticancer agents. These analogs function by incorporating into DNA or RNA during replication, leading to chain termination or the introduction of mutations that can inhibit viral replication or induce cell death in rapidly dividing cancer cells. The unique structural properties of 2,6-Dihydroxy-3-methylpurine make it an attractive scaffold for designing such analogs, as its hydroxyl and methyl substitutions can enhance binding affinity to target enzymes and improve the pharmacokinetic properties of the resulting compounds.

In addition to its role in nucleoside analog development, 2,6-Dihydroxy-3-methylpurine has been studied for its potential as an inhibitor of purine nucleoside phosphorylase (PNP), an enzyme involved in the salvage pathway of purine metabolism. Inhibiting PNP can lead to the accumulation of toxic nucleotides in certain cells, making it a promising strategy for treating specific types of cancer and autoimmune diseases. Studies have shown that derivatives of 2,6-Dihydroxy-3-methylpurine exhibit inhibitory activity against PNP, providing a foundation for the design of more potent and selective inhibitors.

The versatility of 2,6-Dihydroxy-3-methylpurine extends beyond therapeutic applications. Its chemical properties have been exploited in various synthetic methodologies, including the preparation of other purine derivatives and as an intermediate in the synthesis of more complex molecules. The compound's reactivity, particularly at the 2 and 6 hydroxyl positions, allows for the introduction of various functional groups, enabling the exploration of new chemical spaces in drug discovery.

Overall, the discovery of 2,6-Dihydroxy-3-methylpurine has opened up new possibilities in medicinal chemistry and synthetic organic chemistry. Its role as a nucleobase analog and enzyme inhibitor underscores its importance in the ongoing search for novel therapeutic agents. As research continues, 2,6-Dihydroxy-3-methylpurine is likely to play an increasingly prominent role in the development of new drugs and synthetic methodologies, contributing to advancements in both science and medicine.

References

2023. Mixed culture biocatalytic production of the high-value biochemical 7-methylxanthine. Journal of Biological Engineering.
DOI: 10.1186/s13036-022-00316-6

2022. Biocatalytic Production and Purification of the High-value Biochemical Paraxanthine. Biotechnology and Bioprocess Engineering.
DOI: 10.1007/s12257-021-0301-0

2024. Coffee consumption is associated with intestinal Lawsonibacter asaccharolyticus abundance and prevalence across multiple cohorts. Nature Microbiology.
DOI: 10.1038/s41564-024-01858-9