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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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 and antiviral evaluation of nucleoside analogues bearing one pyrimidine moiety and two d-ribofuranosyl residues
Andreeva, Olga V.,Belenok, Mayya G.,Garifullin, Bulat F.,Kataev, Vladimir E.,Lyubina, Anna P.,Man’kova, Maria A.,Saifina, Liliya F.,Semenov, Vyacheslav E.,Shulaeva, Marina M.,Slita, Alexander V.,Volobueva, Alexandrina S.,Voloshina, Alexandra D.,Yesaulkova, Iana L.,Zarubaev, Vladimir V.
, (2021/07/06)
A series of 1,2,3-triazolyl nucleoside analogues in which 1,2,3-triazol-4-yl-β-D-ribofuranosyl fragments are attached via polymethylene linkers to both nitrogen atoms of the heterocycle moiety (uracil, 6-methyluracil, thymine, quinazoline-2,4-dione, alloxazine) or to the C-5 and N-3 atoms of the 6-methyluracil moiety was synthesized. All compounds synthesized were evaluated for antiviral activity against influenza virus A/PR/8/34/(H1N1) and coxsackievirus B3. Antiviral assays revealed three compounds, 2i, 5i, 11c, which showed moderate activity against influenza virus A H1N1 with IC50 values of 57.5 μM, 24.3 μM, and 29.2 μM, respectively. In the first two nucleoside analogues, 1,2,3-triazol-4-yl-β-D-ribofuranosyl fragments are attached via butylene linkers to N-1 and N-3 atoms of the heterocycle moiety (6-methyluracil and alloxazine, respectively). In nucleoside analogue 11c, two 1,2,3-triazol-4-yl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranose fragments are attached via propylene linkers to the C-5 and N-3 atoms of the 6-methyluracil moiety. Almost all synthesized 1,2,3-triazolyl nucleoside analogues showed no antiviral activity against the coxsackie B3 virus. Two exceptions are 1,2,3-triazolyl nucleoside analogs 2f and 5f, in which 1,2,3-triazol-4-yl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranose fragments are attached to the C-5 and N-3 atoms of the heterocycle moiety (6-methyluracil and alloxazine respectively). These compounds exhibited high antiviral potency against the coxsackie B3 virus with IC50 values of 12.4 and 11.3 μM, respectively, although both were inactive against influenza virus A H1N1. According to theoretical calculations, the antiviral activity of the 1,2,3-triazolyl nucleoside analogues 2i, 5i, and 11c against the 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). As to the antiviral activity of nucleoside analogs 2f and 5f against coxsackievirus B3, it can be explained by their interaction with the coat proteins VP1 and VP2.
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.