1H-1,2,3-Triazolo[4,5-d]pyrimidin-7-amine

Description of 1H-1,2,3-Triazolo[4,5-d]pyrimidin-7-amine

1H-1,2,3-Triazolo[4,5-d]pyrimidin-7-amine, commonly known as 8-azadenine (CAS: 1123-54-2), is a purine analogue belonging to the 8-azapurine family. This heterocyclic compound features a fused triazolo-pyrimidine ring system. It exhibits high thermal stability with a melting point exceeding 300°C and limited solubility in DMSO and hot methanol. As a key building block in medicinal chemistry, 8-azadenine serves as a precursor for synthesizing acyclic nucleotide analogs and derivatives with potent biological activities.

Application of 1H-1,2,3-Triazolo[4,5-d]pyrimidin-7-amine

8-Azadenine, a purine analogue, is a versatile building block in medicinal chemistry, primarily employed as a reagent for synthesizing 8-azapurine nucleoside derivatives. These compounds demonstrate potent antiviral activity against viruses like herpes and influenza, inhibiting viral replication through interference with nucleic acid synthesis. It also exhibits antitumor effects in experimental models by disrupting tumor cell metabolism and ribonucleotide reductase activity. As a xanthine oxidase inhibitor (IC₅₀ ≈ 0.54 μM), it holds potential for managing gout and oxidative stress-related conditions.

Storage of 1H-1,2,3-Triazolo[4,5-d]pyrimidin-7-amine

It should be kept in a cool, dry, and dark environment to maintain stability and prevent degradation. Recommended conditions include refrigeration under an inert atmosphere, such as nitrogen, to minimize oxidation. Protect from light exposure and moisture. For short-term storage, 0-4°C in a desiccator is suitable; for long-term, consider -20°C. Always use airtight containers.