28279-62-1

Usage

Uses

Used in Medicinal Chemistry:
2-pentofuranosyl-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine is utilized as a key component in the development of new pharmaceutical drugs due to its unique structure and potential for novel biological activities and interactions with biological targets.
Used in Pharmaceutical Drug Development:
In the pharmaceutical industry, 2-pentofuranosyl-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine is employed as a precursor or building block for the synthesis of new drug molecules, leveraging its distinctive structure to create compounds with potential therapeutic applications.
Used in Nucleoside Analog Research:
Given the presence of the pentofuranosyl group, 2-pentofuranosyl-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine is used as a nucleoside analog in research aimed at developing treatments for viral infections or cancer, capitalizing on its potential to interact with cellular processes at a molecular level.
Further studies are necessary to fully explore the properties and potential applications of 2-pentofuranosyl-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine, ensuring that its use in these areas is grounded in a comprehensive understanding of its characteristics and effects.

Upstream product

• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 4471-88-9 N⁶-nonanoyl-8-azaadenine 

Relevant academic research and scientific papers

High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries

The Vorbrueggen glycosylation reaction was adapted into a one-step 5 min/130 °C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl inflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield ± SD was 26 ± 16%, and the average purity ± SD was 95 ± 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.

8-Azaadenosine and its 2'-deoxyribonucleoside: Synthesis and oligonucleotide base-pair stability

The synthesis of 8-azaadenosine (1a; z8A) has been performed by SnCl4- catalyzed glycosylation of 8-azaadenine (4) with 1,2,3,5-tetra-O-acetyl-β- D-ribofuranose (5), followed by the separation of the regioisomers 6 an d7 and subsequent deacetylation. The ribonucleoside 1a as well as its 2'-deoxy derivative 1b (z8A(d)) were converted into oligonucleotide building blocks- the phosphonate 2 as well as the phosphoramidites 3 and 19. They were used to prepare the oligoribonucleotide (z8A-U)6 and oligodeoxyribonucleotides. The T(m) values and the thermodynamic data of duplex formation of the modified duplexes showed no significant changes compared to those containing A(d) or A residues. This indicates that the stereoelectronic effect of the 8-azaadenine base which was found for the monomeric nucleoside has only a minor influence on the duplex stability.