67410-59-7Relevant academic research and scientific papers
Nucleobase-Functionalized 5-Aza-7-deazaguanine Ribo- A nd 2′-Deoxyribonucleosides: Glycosylation, Pd-Assisted Cross-Coupling, and Photophysical Properties
Leonard, Peter,Kondhare, Dasharath,Jentgens, Xenia,Daniliuc, Constantin,Seela, Frank
, p. 13313 - 13328 (2019)
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.
Ribonucleoside analogs with novel hydrogen bonding patterns
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Page/Page column 15, (2013/03/26)
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
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Page/Page column 10, (2010/10/19)
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
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, (2008/06/13)
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.
