67410-65-5

Usage

Uses

Used in Antiviral Applications:
2-Amino-8-D-Ribofuranosyl-imidazo[1,2-a]-1,3,5-triazin-4(8H)-one is used as an antiviral agent for the treatment of influenza. It targets the viral replication process, thereby inhibiting the spread of the virus and alleviating the symptoms associated with the infection.
Used in Broad-Spectrum Antiviral Applications:
In addition to its effectiveness against influenza, 2-Amino-8-D-Ribofuranosyl-imidazo[1,2-a]-1,3,5-triazin-4(8H)-one also functions as a broad-spectrum inhibitor of viruses in the Flaviviridae family. This makes it a valuable compound for the development of antiviral therapies against a wide range of viral infections, including but not limited to hepatitis C, dengue, and West Nile virus.
Used in Pharmaceutical Industry:
2-Amino-8-D-Ribofuranosyl-imidazo[1,2-a]-1,3,5-triazin-4(8H)-one is used as a key component in the development of antiviral drugs within the pharmaceutical industry. Its unique structure and antiviral properties make it a promising candidate for the creation of new medications to combat viral diseases.
Used in Research and Development:
In the field of virology and medicinal chemistry, 2-Amino-8-D-Ribofuranosyl-imidazo[1,2-a]-1,3,5-triazin-4(8H)-one is used as a research compound to study the mechanisms of viral replication and to develop new strategies for antiviral drug design. Its unique chemical structure provides valuable insights into the interactions between viral enzymes and potential inhibitors.
Used in Diagnostic Applications:
2-Amino-8-D-Ribofuranosyl-imidazo[1,2-a]-1,3,5-triazin-4(8H)-one can also be used in diagnostic applications, such as the development of assays to detect the presence of specific viruses or to monitor the effectiveness of antiviral treatments. Its unique chemical properties make it a useful tool for the detection and analysis of viral infections.

InChI:InChI=1/C10H13N5O5/c11-8-12-9-14(1-2-15(9)10(19)13-8)7-6(18)5(17)4(3-16)20-7/h1-2,4-7,16-18H,3H2,(H2,11,13,19)/t4-,5-,6-,7-/m0/s1

Upstream product

• 67410-64-4 2-aminoimidazo<1,2-a>-s-triazin-4(8H)-one 
• 58-96-8 uridine 
• 67410-59-7 2-amino-8-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-imidazo[1,2-a]-s-triazin-4-one 

Relevant academic research and scientific papers

Nucleobase-Functionalized 5-Aza-7-deazaguanine Ribo- A nd 2′-Deoxyribonucleosides: Glycosylation, Pd-Assisted Cross-Coupling, and Photophysical Properties

The special nucleobase recognition pattern of 5-aza-7-deazaguanine nucleosides makes them valuable for construction of homo purine DNA, silver-mediated base pairs, and expansion of the four letter genetic coding system. To widen the utility of 5-aza-7-deazaguanine nucleosides, side chains were introduced at position-7 of the nucleobase. As key compounds, 7-iodo nucleosides were synthesized. Nucleobase anion glycosylation of the iodo derivative of isobutyrylated 5-aza-7-deazaguanine with the bromo sugar of 2,3,5-tri-O-benzoyl-1-O-acetyl-d-ribofuranose gave the pure β-D anomeric N-9 glycosylation product (67%), whereas one-pot Vorbrüggen conditions gave only 42% of the iodinated nucleoside. The noniodinated nucleoside was formed in 84%. For the synthesis of 2′-deoxyribonucleosides, anion glycosylation performed with Hoffer's 2′-deoxyhalogenose yielded an anomeric mixture (α-D = 33% and β-D = 39%) of 2′-deoxyribonucleosides. Various side chain derivatives were prepared from nonprotected nucleosides by Pd-assisted Sonogashira or Suzuki-Miyaura cross-coupling. Among the functionalized ribonucleosides and anomeric 2′-deoxyribonucleosides, some of them showed strong fluorescence. Benzofuran and pyrene derivatives display high quantum yields in non-aqueous solvents and solvatochromism. Single-crystal X-ray analysis of 7-iodo-5-aza-7-deaza-2′-deoxyguanosine displayed intermolecular iodo-oxygen interactions in the crystal and channels filled with solvent molecules.

Recognition of Artificial Nucleobases by E. coli Purine Nucleoside Phosphorylase versus its Ser90Ala Mutant in the Synthesis of Base-Modified Nucleosides

A wide range of natural purine analogues was used as probe to assess the mechanism of recognition by the wild-type (WT) E. coli purine nucleoside phosphorylase (PNP) versus its Ser90Ala mutant. The results were analyzed from viewpoint of the role of the Ser90 residue and the structural features of the bases. It was found that the Ser90 residue of the PNP 1) plays an important role in the binding and activation of 8-aza-7-deazapurines in the synthesis of their nucleosides, 2) participates in the binding of α-D-pentofuranose-1-phosphates at the catalytic site of the PNP, and 3) catalyzes the dephosphorylation of intermediary formed 2-deoxy-α-D-ribofuranose-1-phosphate in the trans-2-deoxyribosylation reaction. 5-Aza-7-deazaguanine manifested excellent substrate activity for both enzymes, 8-amino-7-thiaguanine and 2-aminobenzothiazole showed no substrate activity for both enzymes. On the contrary, the 2-amino derivatives of benzimidazole and benzoxazole are substrates and are converted into the N1- and unusual N2-glycosides, respectively. 9-Deaza-5-iodoxanthine showed moderate inhibitory activity of the WT E. coli PNP, whereas 9-deazaxanthine and its 2′-deoxyriboside are weak inhibitors. How does it work? The substrate and inhibitory properties of a wide range of artificial bases for the wild-type E. coli purine nucleoside phosphorylase (PNP) versus its Ser90Ala mutant were studied to evaluate the mechanism of recognition by PNP and the role of various electronic and structural features in this process. The PNP recognized a broad palette of bases consisting of a number of dissimilar fragments determining its ability to interact with the Asp204 and Ser90 residues (see scheme).

Ribonucleoside analogs with novel hydrogen bonding patterns

This invention relates to nucleoside, nucleotide, and oligonucleotide analogs that incorporate non-standard nucleobase analogs, defined to be those that present a pattern of hydrogen bonds to a paired nucleobase analog in a complementary strand that is different from the pattern presented by adenine, guanine, cytosine, and thymine. The invention is specifically concerned with nucleotide analogs that present the donor-donor-acceptor, hydrogen bonding patterns on pyrimidine analogs, and especially those that are analogs of ribonucleotides, including protected ribonucleotides suitable for phosphoramidite-based synthesis of RNA. The heterocycles on these nucleoside analogs are aminopyridones that have electron withdrawing groups attached to the position analogous to the 5-position of the ring in standard pyrimidines, including nitro, cyano, and carboxylic acid derivatives.

Broad-spectrum inhibitor of viruses in the Flaviviridae family

The present invention relates generally to the fields of chemistry and molecular biology. More particularly, it concerns the use of compounds to treat viral infection. In a preferred embodiment, 2-amino-8-(β-D-ribofuranosyl) imidazo [1,2-a]-s-triazine-4-o

Imidazo[1,2-a]-s-triazine

Imidazo[1,2-a]-s-triazines including the base, the nucleoside, derivatives of the nucleoside, and the 5' nucleotide are prepared and are useful as antiviral Agents against RNA viruses.