13035-61-5Relevant articles and documents
A facile synthesis of 9-(1,3-dihydroxy-2-propoxymethyl)guanine (ganciclovir) from guanosine
Boryski, Jerzy,Golankiewicz, Bozenna
, p. 625 - 628 (1999)
The potent and selective antiviral drug ganciclovir (6) has been synthesized in two steps via transpurination of fully acetylated guanosine (1) in the presence of 1,3-diacetoxy-2-(acetoxymethoxy)propane (2), followed by deacetylation in aqueous ammonia. The transpurination reaction also provides valuable side products, tetra-O-acetyl-β-D-ribofuranose (5) and the 7-regioisomer of triacetylganciclovir (4); the latter product can be converted to the desired 9-isomer in a thermal 7 ? 9 isomerization.
An unusual transformation of isometric forms of tetra acetyl D-ribofuranose.
DAVOLL,BROWN,VISSER
, p. 64 - 65 (1952)
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A Practical and Convenient Method for Utilization of the Mother Liquors Containing 1,2,3,5-Tetra-O-Acetyl-α-D-Ribofuranose
Mei,Guan,Li
, p. 592 - 596 (2018)
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The First Analog of Pyrimidine Nucleosides with Two Nucleobases and Two d-Ribofuranose Residues
Andreeva,Saifina,Belenok,Semenov,Kataev
, p. 292 - 296 (2021/03/26)
Abstract: The reaction of 1,5-bis[1-(prop-2-yn-1-yl)uracil-3-yl]pentane with 2',3',5'-tri-O-acetyl-β-d-ribofuranosylazide followed by removing of acetyl protective groups with a solution of sodium methylate in methanol afforded 1,5-bis{[1-methyl(β-d-ribofuranosyl)-1H-1,2,3-triazole-4-yl]uracil-3-yl}pentane which is the first analog of pyrimidine nucleosides with two nucleobases and two d-ribofuranose residues.
Synthesis of 1,2,3-triazolyl nucleoside analogues and their antiviral activity
Andreeva, Olga V.,Garifullin, Bulat F.,Zarubaev, Vladimir V.,Slita, Alexander V.,Yesaulkova, Iana L.,Saifina, Liliya F.,Shulaeva, Marina M.,Belenok, Maya G.,Semenov, Vyacheslav E.,Kataev, Vladimir E.
, p. 473 - 490 (2020/09/22)
Abstract: Based on the fact that a search for influenza antivirals among nucleoside analogues has drawn very little attention of chemists, the present study reports the synthesis of a series of 1,2,3-triazolyl nucleoside analogues in which a pyrimidine fragment is attached to the ribofuranosyl-1,2,3-triazol-4-yl moiety by a polymethylene linker of variable length. Target compounds were prepared by the Cu alkyne-azide cycloaddition (CuAAC) reaction. Derivatives of uracil, 6-methyluracil, 3,6-dimethyluracil, thymine and quinazolin-2,4-dione with ω-alkyne substituent at the N1 (or N5) atom and azido 2,3,5-tri-O-acetyl-D-β-ribofuranoside were used as components of the CuAAC reaction. All compounds synthesized were evaluated for antiviral activity against influenza virus A/PR/8/34/(H1N1) and coxsackievirus B3. The best values of IC50 (inhibiting concentration) and SI (selectivity index) were demonstrated by the lead compound 4i in which the 1,2,3-triazolylribofuranosyl fragment is attached to the N1 atom of the quinazoline-2,4-dione moiety via a butylene linker (IC50 = 30?μM, SI = 24) and compound 8n in which the 1,2,3-triazolylribofuranosyl fragment is attached directly to the N5 atom of the 6-methyluracil moiety (IC50 = 15?μM, SI = 5). According to theoretical calculations, the antiviral activity of the 1,2,3-triazolyl nucleoside analogues 4i and 8n against H1N1 (A/PR/8/34) influenza virus can be explained by their influence on the functioning of the polymerase acidic protein (PA) of RNA-dependent RNA polymerase (RdRP). Graphic abstract: [Figure not available: see fulltext.]
Synthesis of benzimidazole nucleosides and their anticancer activity
Khan, Ayesha,Lawande, Pravin P.,Shinde, Vaishali S.,Sontakke, Vyankat A.
supporting information, (2020/10/12)
An efficient route for the synthesis of benzimidazole nucleosides 1–8 from readily available D-glucose via 3,5-dihydroxy-1,2-O-isopropylidene-α-D-ribofuranose and 3-azido-3-deoxy-1,2-O-isopropylidene-α-D-xylofuranose intermediates has been adopted. Ribofuranosyl nucleosides 1–4 with different benzimidazole bases, and 3?-deoxy-3?-azido-ribofuranosyl nucleosides 5–8, as another series, were obtained. All these newly synthesized analogs were evaluated for anticancer activity using MDA-MB-231 cell line. Among the differently substituted derivatives, 3?-azide substituted nucleosides (5–8) are more potent compared to ribofuranosyl analogs 1–4. The C-3?-azido analog 8 having anthryl group at 2-position of nucleobase show almost similar potency as that of standard etoposide.
