110415-62-8Relevant articles and documents
SELECTIVE DEUTERATION OVER RANEY NICKEL IN DEUTERIUM OXIDE: METHYL GLYCOSIDES
Angyal, Stephen J.,Stevens, John D.,Odier, Leon
, p. 83 - 94 (1986)
The rate of protium-deuterium exchange, catalyzed by deuterated Raney nickel in deuterium oxide, in various positions in methyl glycopyranosides and furanosides has been studied.In general, the exchange process is not highly regioselective in these compounds.However, conditions were found under which methyl β-D-fructopyranoside can be selectively labelled on C-5, methyl β-D-fructofuranoside on C-3, and methyl β-D-galactopyranoside on C-3 and C-4.
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)
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.
Selective monodeacetylation of methyl 2,3,5-tri-O-acetyl-D- arabinofuranoside using biocatalyst
Sook, Jin Jun,Man, Sik Moon,So, Ha Lee,Chan, Seong Cheong,Kwan, Soo Kim
, p. 5063 - 5065 (2005)
Methyl arabinofuranoside 1 was fully acetylated to methyl 2,3,5-tri-O-acetyl-d-arabinofuranoside 2 and it was regioselectively deacetylated using enzymes. Rhizopus oryzae esterase gave methyl 3,5-di-O-acetyl-d-arabinofuranoside 3, regioselectively. This protected 3 was deoxygenized to 3,5-di-O-acetyl-d-2-deoxyarabinofuranoside 7 using hypophosphorous acid.
Synthesis of the enantiomer of nelarabine
Herbal, Karim,Kitteringham, John,Voyle, Martyn,Whitehead, Andrew J.
, p. 2961 - 2964 (2005)
A synthesis of the enantiomer of nelarabine is described. Subtle changes in the protecting group strategy allow for an efficient inversion of the C-2′ stereocentre.
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.]
Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation
Andreeva, Olga V.,Garifullin, Bulat F.,Sharipova, Radmila R.,Strobykina, Irina Yu.,Sapunova, Anastasiya S.,Voloshina, Alexandra D.,Belenok, Mayya G.,Dobrynin, Alexey B.,Khabibulina, Leysan R.,Kataev, Vladimir E.
, p. 2367 - 2380 (2020/08/28)
Several glycoconjugates of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with a 1,2,3-triazolyl moiety were synthesized, and their cytotoxicity was evaluated against some human cancer and normal cell lines. Most of the synthesized compounds demonstrated weak inhibitory activities against the M-HeLa and MCF-7 human cancer cell lines. Three lead compounds, 54, 56 and 57, exhibited high selective cytotoxic activity against M-HeLa cells (IC50 = 1.7-1.9 μM) that corresponded to the activity of the anticancer drug doxorubicin (IC50 = 3.0 μM). Moreover, the lead compounds were not cytotoxic with respect to a Chang liver human normal cell line (IC50 > 100 μM), whereas doxorubicin was cytotoxic to this cell line (IC50 = 3.0 μM). It was found that cytotoxic activity of the lead compounds is due to induction of apoptosis proceeding along the mitochondrial pathway. The present findings suggest that 1,2,3-triazolyl-ring-containing glycoconjugates of isosteviol are a promising scaffold for the design of novel anticancer agents.
