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Journal articles on the topic 'Ribofuranosyl'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Hanaya, Tadashi, Kiyoshi Torigoe, Kazuyuki Soranaka, Hiroshi Fujita, Wolfgang Pfleiderer та Hiroshi Yamamoto. "An Efficient Synthesis of 2'-O-(β-D-Ribofuranosyl)biopterin". Pteridines 19, № 1 (2008): 72–78. http://dx.doi.org/10.1515/pteridines.2008.19.1.72.

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AbstractN2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O-(trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively afforded the corresponding 2'-O-(2,3,5-tri-Oacetyl- and 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)biopterin derivatives (6a, 42% and 6b, 60%) as major products. Removal of the protecting groups of 6b provided 2'-O-(β-D-ribofuranosyl)biopterin (1c, 87% overall yield) in 3 steps.

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2

Spassova, Maria K., Antonín Holý, and Milena Masojídková. "Ribonucleosides of 3-amino- and 3,5-diaminopyrazole-4-carboxylic acid and their open-chain analogues: Synthesis and reactions." Collection of Czechoslovak Chemical Communications 51, no. 7 (1986): 1512–31. http://dx.doi.org/10.1135/cccc19861512.

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Bis(trimethylsilyl) derivative of ethyl 3-aminopyrazole-4-carboxylate (VI) and tris(trimethylsilyl) derivative of ethyl 3,5-diaminopyrazole-4-carboxylate (VII) on reaction with 2,3,5-tri-O-benzoyl-D-ribofuranolyl chloride and subsequent debenzoylation afforded the respective β-D-ribofuranosyl derivatives VIIIa and Xa. Their alkaline hydrolysis led to 1-(β-D-ribofuranosyl)-3-aminopyrazole-4-carboxylic acid (VIIIc) and 1-(β-D-ribofuranosyl)-3,5-diaminopyrazole-4-carboxylic acid (Xb). The esters VIIIa and Xa were not ammonolyzed under normal conditions. Contrary to nucleosidation of the silyl der

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3

Tiwari, Sangeeta, Ashok K. Yadav, and A. K. Mishra. "Some New Pyrido[2,3-d]pyridimines and their Nucleoside of Biological Importance." E-Journal of Chemistry 7, s1 (2010): S85—S92. http://dx.doi.org/10.1155/2010/812567.

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Chalcones (I) reacted with malanonitrile and ammonium acetate yielded 2-amino-3-cyano-4,6-disubstituted pyridines (II) in excellent yield. 4-Amino-5,7-disubstituted pyrido [2,3-d]pyrimidine-2(1H)-thiones (III), 4-amino-5,7-disubstituted pyrido[2,3-d]pyrimidines (IV) and 4-imino-3,5,7-trisubstituted pyrido[2,3-d]pyrimidin-2(1H)-ones (V) have been synthesized by the condensation of compound (II) with thiourea, formamide and arylisocynate respectively. The ribofuranosidesviz. 4-amino-5,7-disubstituted-1- [2',3',5'-tri-o-benzoyl-β,D-ribofuranosyl]pyrido[2,3-d]pyrimidine-2-(1H)-thiones (VI) and 4-i

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4

Luo, Yan, та David L. Zechel. "A concise synthesis of α-D-ribofuranosyl alkylphosphonates Putative substrate intermediates for the carbonphosphorous lyase system". Canadian Journal of Chemistry 84, № 4 (2006): 743–47. http://dx.doi.org/10.1139/v06-038.

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Carbonphosphorous lyase is a multienzyme system found in many species of bacteria that is distinguished by its ability to hydrolyze a broad array of unactivated alkylphosphonates. α-D-Ribofuranosyl alkylphosphonates are potential metabolic intermediates generated by the carbonphosphorous lyase pathway. Here we describe a facile synthesis of α-D-ribofuranosyl alkylphosphonates using β-D-ribofuranosyl trichloracetimidate as a glycosyl donor.Key words: carbonphosphorous lyase, phn operon, phnN, phosphonates, glycosyl trichloroacetimidate donor, α-D-ribofuranosyl ethylphosphonate.

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5

Otmar, Miroslav, Ivan Rosenberg, Milena Masojídková, and Antonín Holý. "[5-(Adenin-9-yl)-5-deoxy-L-pentofuranosyl]phosphonates - A Novel Type of Nucleotide Analogs Related to HPMPA. II. Synthesis of L-ribo and L-xylo Configurated Derivatives by Recyclization of Diethyl (5-RS)-[1,2-O-Isopropylidene-5-O-methanesulfonyl-D-pentofuranos-5-C-yl]phosphonates under Acidic Conditions." Collection of Czechoslovak Chemical Communications 58, no. 9 (1993): 2180–96. http://dx.doi.org/10.1135/cccc19932180.

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Further cyclic analogs of the antiviral (S)-9-(3-hydroxy-2-phosphonomethoxypropyl)adenine (I) were prepared: both anomers of [5-(adenin-9-yl)-5-doxy-L-ribofuranosyl]phosphonic acid (α-IId and β-IId) and [5-(adenin-9-yl)-5-doxy-α-L-ribofuranosyl]phosphonic acid (IIe). Recyclization reaction of diethyl (5RS-(3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-D-ribofuranos-5-C-yl)phosphonate (IVb) and diethyl (5RS-(3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-D-xylofuranos-5-C-yl)phosphonate (IVd) in trifluoroacetic acid led to cyclic aldehydes Va and Vb which were reduced to diethyl α- a

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6

Nauš, Petr, Martin Kuchař, and Michal Hocek. "Cytostatic and Antiviral 6-Arylpurine Ribonucleosides IX. Synthesis and Evaluation of 6-Substituted 3-Deazapurine Ribonucleosides." Collection of Czechoslovak Chemical Communications 73, no. 5 (2008): 665–78. http://dx.doi.org/10.1135/cccc20080665.

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A series of 3-deazapurine ribonucleosides 5a-5l bearing diverse C-substituents (alkyl, aryl and heteroaryl) in the position 6 were prepared by Pd-catalyzed cross-coupling reactions of either free 6-chloro-3-deazapurine ribonucleoside 4 or its acetyl protected congener 3 followed by deprotection. An improved synthesis of the starting 4-chloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-imidazo[4,5-c]pyridine (3) was developed by the application of Vorbrüggen glycosylation of silylated nucleobase with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (2). None of compounds 5a-5l showed any considerable cy

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7

Tatarinov, Dmitry A., Bulat F. Garifullin, Mayya G. Belenok, et al. "The First 5′-Phosphorylated 1,2,3-Triazolyl Nucleoside Analogues with Uracil and Quinazoline-2,4-Dione Moieties: A Synthesis and Antiviral Evaluation." Molecules 27, no. 19 (2022): 6214. http://dx.doi.org/10.3390/molecules27196214.

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A series of 5′-phosphorylated (dialkyl phosphates, diaryl phosphates, phosphoramidates, H-phosphonates, phosphates) 1,2,3-triazolyl nucleoside analogues in which the 1,2,3-triazole-4-yl-β-D-ribofuranose fragment is attached via a methylene group or a butylene chain to the N-1 atom of the heterocycle moiety (uracil or quinazoline-2,4-dione) was synthesized. All compounds were evaluated for antiviral activity against influenza virus A/PR/8/34/(H1N1). Antiviral assays revealed three compounds, 13b, 14b, and 17a, which showed moderate activity against influenza virus A (H1N1) with IC50 values of 1

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8

Break, Laila Mohammed, та Wafa Saad Al-harthi. "Synthesis New of Nucleoside of 1,3-bis-(2,3,5-tri-O-Benzoyl-β-D-Ribofuranosyl)-8-(Trifluoromethyl)-2-Methyl-4-Quinazolinone". Proceedings 9, № 1 (2018): 57. http://dx.doi.org/10.3390/ecsoc-22-05694.

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Fluorinated nucleosides are very important for increased biological and chemical stability of organ fluorine compounds. Synthesis of (1H)-8-trifluloromethyl-2-methyl-4-quinazolinone 3 from 2-amino-3-(trifluoromethyl) benzoic acid 1 was performed. Ribosylation of compound 4 with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose 5 using the silylation method created the benzoylated nucleoside derivative 6. Debenzoylation of the protected nucleoside 6 via reaction with sodium metal in dry methanol to create the corresponding free nucleoside 1,3-bis-(2,3,5-tri-O-benzoyl-β-d-ribofuranosyl)-8-(trifluo

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9

Guglielmi, Hans, Markus Dachtler, and Klaus Albert. "Imidazole Nucleosides, V. Synthesis of 3′-Fluoro-3′-deoxy-ribofuranosides of 4(5)-Amino-imidazoIe-5(4)carboxamide." Zeitschrift für Naturforschung B 54, no. 8 (1999): 1055–60. http://dx.doi.org/10.1515/znb-1999-0814.

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The synthesis of the 3′-fluoro-derivatives of 5-amino-1-(β-D-ribofuranosyl)imidazole-4- carboxamide (AICA-riboside) and the isomeric 4-amino-1(β-D-ribofuranosyl)imidazole-5- carboxamide (iso-AICA-riboside) are described. Structures were confirmed by elemental analysis, UV and 1H NMR spectroscopy. The anti-viral and anti-cancer activities of these imidazole nucleosides were tested.

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10

Andreeva, Olga V., Bulat F. Garifullin, Vladimir V. Zarubaev, et al. "Synthesis and Antiviral Evaluation of Nucleoside Analogues Bearing One Pyrimidine Moiety and Two D-Ribofuranosyl Residues." Molecules 26, no. 12 (2021): 3678. http://dx.doi.org/10.3390/molecules26123678.

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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 o

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11

Krečmerová, Marcela, Hubert Hřebabecký, Milena Masojídková, and Antonín Holý. "Synthesis of 5-Phenyl-2(1H)-pyrimidinone Nucleosides." Collection of Czechoslovak Chemical Communications 61, no. 3 (1996): 458–77. http://dx.doi.org/10.1135/cccc19960458.

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Reaction of 2-phenyltrimethinium salt 1 with thiourea and subsequent reaction with chloroacetic acid afforded 5-phenyl-2(1H)-pyrimidinone (3). Its silyl derivative 4 was condensed with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose under catalysis with tin tetrachloride or trimethylsilyl trifluoromethanesulfonate to give protected nucleoside 5 together with 5',O6-cyclo-5-phenyl-1,3-bis- (β-D-ribofuranosyl)-6-hydroxy-5,6-dihydro-2(1H,3H)-pyrimidinone (7). The greatest amounts of 7 were formed with the latter catalyst. Nucleosidation of the silyl derivative 4 with protected methyl 2-deoxy-D-ribof

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12

Wilcox, Craig S., and Renee M. Otoski. "Stereoselective preparations of ribofuranosyl chlorides and ribofuranosyl acetates.Solvent effects and stereoselectivity in the reaction of ribofuranosyl acetates with trimethylallylsilane." Tetrahedron Letters 27, no. 9 (1986): 1011–14. http://dx.doi.org/10.1016/s0040-4039(86)80035-1.

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13

Prichard, Mark N., Samuel L. Frederick, Shannon Daily, et al. "Benzimidazole Analogs Inhibit Human Herpesvirus 6." Antimicrobial Agents and Chemotherapy 55, no. 5 (2011): 2442–45. http://dx.doi.org/10.1128/aac.01523-10.

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ABSTRACTSeveral benzimidazole nucleoside analogs, including 1H-β-d-ribofuranosyl-2-bromo-5,6-dichlorobenzimidazole (BDCRB) and 1H-β-l-ribofuranosyl-2-isopropylamino-5,6-dichlorobenzimidazole (maribavir [MBV]), inhibit the replication of human cytomegalovirus. Neither analog inhibited the related betaherpesvirus human herpesvirus 6 (HHV-6). Additional analogs of these compounds were evaluated against both variants of HHV-6, and twol-analogs of BDCRB had good antiviral activity against HHV-6A, as well as more modest inhibition of HHV-6B replication.

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14

Wilcox, C. "Stereoselective preparations of ribofuranosyl chlorides and ribofuranosyl acetates. Solvent effects and stereoselectivity in the reaction of ribofuranosyl acetates with trimethylallylsilane." Tetrahedron Letters 29, no. 9 (1986): 1011–14. http://dx.doi.org/10.1016/s0040-4039(00)84164-7.

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15

Frister, Hermann, and Eckhard Schlimme. "Ringöffnungsreaktionen an bioreaktiven Lactamsystemen / Ring Opening Reactions of Bioreactive Lactam Systems." Zeitschrift für Naturforschung C 42, no. 5 (1987): 603–12. http://dx.doi.org/10.1515/znc-1987-0518.

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Abstract 1-β-ᴅ-Ribofuranosylpyrrolidin-2,5-dione (9) was synthesized by ribosylation of N-silylated succinimide (7) with 1,2,3,5-tetra-O-acetyl-β-ᴅ-ribofuranose in acetonitril in the presence of tin tetrachloride. The compounds 9, 1-β-ᴅ-ribofuranosyl-l-H-pyrrol-2,5-dione (5) and N-methyl- maleinimide (2) were converted with ammonia to the ring-opened components 16. 14 and 15. The bioreactivity of the N-maleinimide derivatives 2 and 5 with respect to addition and ring-opening reactions with amino acid side chains containing either thiol or amino groups was shown in model reactions with glutathi

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16

Karskela, Tuomas, Karel D. Klika та Harri Lönnberg. "Synthesis of 7-substituted 3-β-D-ribofuranosyl-3H-imidazo[2,1-i]purines". Collection of Czechoslovak Chemical Communications 76, № 8 (2011): 1043–54. http://dx.doi.org/10.1135/cccc2011069.

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A method for the synthesis of 7-substituted 3-β-D-ribofuranosyl-3H-imidazo[2,1-i]purines has been devised whereby compounds were prepared in a few steps from a common intermediate, 3-(2′,3′-O-isopropylidene-β-D-ribofuranosyl)-3H-imidazo[2,1-i]purine-7-carbaldehyde, obtained from the reaction of 2′,3′-O-isopropylideneadenosine with bromomalonaldehyde. The formyl group of the carbaldehyde was subsequently reductively aminated and the resulting secondary amines were then further derivatized either by acylation, lactamization or reductive alkylation.

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17

Dabbs, E. R., K. Yazawa, Y. Mikami, et al. "Ribosylation by mycobacterial strains as a new mechanism of rifampin inactivation." Antimicrobial Agents and Chemotherapy 39, no. 4 (1995): 1007–9. http://dx.doi.org/10.1128/aac.39.4.1007.

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Several fast-growing Mycobacterium strains were found to inactivate rifampin. Two inactivated compounds (RIP-Ma and RIP-Mb) produced by these organisms were different from previously reported derivatives, i.e., phosphorylated or glucosylated derivatives, of the antibiotic. The structures of RIP-Ma and RIP-Mb were determined to be those of 3-formyl-23-[O-(alpha-D-ribofuranosyl)]rifamycin SV and 23-[O-(alpha-D-ribofuranosyl)]rifampin, respectively. To our knowledge, this is the first known example of ribosylation as a mechanism of antibiotic inactivation.

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18

Hocek, Michal, Dana Hocková, and Jan Štambaský. "Cytostatic 6-Arylpurine Nucleosides V. Synthesis of 8-Substituted 6-Phenylpurine Ribonucleosides." Collection of Czechoslovak Chemical Communications 68, no. 5 (2003): 837–48. http://dx.doi.org/10.1135/cccc20030837.

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Regioselective Suzuki-Miyaura reaction of 8-bromo-6-iodo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine with phenylboronic acid gave 8-bromo-6-phenylpurine derivative that was used for cross-coupling reactions (with PhB(OH)2, Me3Al, Et3Al, BnZnCl) or nucleophilic substitutions (with NaOH, NaOMe, NH3, NHMe2 or thiourea). A series of 8-X-substituted 6-phenyl-9-(β-D-ribofuranosyl)purines (X = Ph, Me, Et, Bn, OH, OMe, NH2, NMe2, SH) was prepared in this way directly or after deprotection. None of the title nucleosides exhibited any considerable cytostatic activity.

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19

Latosińska, Jolanta Natalia, Magdalena Latosińska, Janez Seliger, Veselko Žagar, and Tomaž Apih. "Anti-Butterfly Effect in Ribavirin Studied by Combined Experiment (PXRD/1H-14N NQR Cross-Relaxation Spectroscopy), Quantum Chemical Calculations, Molecular Docking, Molecular Dynamics Simulations, and Novel Structure-Binding Strength and Quadrupolar Indices." Molecules 30, no. 5 (2025): 1096. https://doi.org/10.3390/molecules30051096.

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Ribavirin, 1-(β-D-Ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide, which is included in the list of drugs recommended in the guidelines for the diagnosis and treatment of SARS-CoV-2 infection, has been the subject of experimental and theoretical investigation. The most thermodynamically stable polymorphic form was studied using 1H-14N NQR cross-relaxation, periodic DFT/QTAIM/RDS/3D Hirshfeld surfaces, and molecular docking. For the first time, a 1H-14N cross-relaxation spectrum of ribavirin was recorded and interpreted. Twelve resonance frequencies were assigned to four inequivalent nitrogen po

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20

P, Angalammal, Sivakumari K, Rajesh S, and Shyamala Devi K. "2-Carbamyl-9-[Beta-D-Ribofuranosyl] hypoxanthine from Rambutan fruit as potential inhibitor of apoptotic proteins:In silico molecular docking approach." International Journal of Zoology and Applied Biosciences 7, no. 6S (2022): 1–6. http://dx.doi.org/10.55126/ijzab.2022.v07.i06.sp002.

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The fruit of the rambutan tree, Nephelium lappaceum, is an important source of physiologically active substances that have the ability to induce apoptosis. Because of this, the goal of the current work was to anticipate how the GC-MS spectrum compound from Nephelium lappaceum (2-Carbamyl-9-[Beta-D-Ribofuranosyl] Hypoxanthine]) would interact with apoptotic proteins (Caspase-3, Caspase-9, -Actin, p53, and Bcl-2) using the PatchDock docking program. As a result of the Lipinski rule, 2-Carbamyl-9-[Beta-D-Ribofuranosyl] Hypoxanthine is recommended as the best cancer treatment. The use of a molecul

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21

Lieberknecht, Albrecht, Johannes Schmidt, and John J. Stezowski. "Diastereoselective synthesis of ribofuranosyl glycines." Tetrahedron Letters 32, no. 19 (1991): 2113–16. http://dx.doi.org/10.1016/s0040-4039(00)71250-0.

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22

Fateev, Ilja V., Ekaterina V. Sinitsina, Aiguzel U. Bikanasova, et al. "Thermophilic phosphoribosyltransferases Thermus thermophilus HB27 in nucleotide synthesis." Beilstein Journal of Organic Chemistry 14 (December 21, 2018): 3098–105. http://dx.doi.org/10.3762/bjoc.14.289.

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Phosphoribosyltransferases are the tools that allow the synthesis of nucleotide analogues using multi-enzymatic cascades. The recombinant adenine phosphoribosyltransferase (TthAPRT) and hypoxanthine phosphoribosyltransferase (TthHPRT) from Thermus thermophilus HB27 were expressed in E.coli strains and purified by chromatographic methods with yields of 10–13 mg per liter of culture. The activity dependence of TthAPRT and TthHPRT on different factors was investigated along with the substrate specificity towards different heterocyclic bases. The kinetic parameters for TthHPRT with natural substra

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23

Votruba, Ivan, Antonín Holý, Hana Dvořáková та ін. "Synthesis of 2-Deoxy-β-D-ribonucleosides and 2,3-Dideoxy-β-D-pentofuranosides on Immobilized Bacterial Cells". Collection of Czechoslovak Chemical Communications 59, № 10 (1994): 2303–30. http://dx.doi.org/10.1135/cccc19942303.

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Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as their aza and deaza analogs. All experiments invariably gave β-anomers; in most cases, the reaction was regiospecific, affording N9-isomers in the purine and N1-isomers in the pyrimidine series. Also a 2,3-dideoxynucleoside can serve as donor of the glycosyl moiety. The acceptor activity of purine bases depends only little on substitution, the only condition being the presence of N7-nitrogen atom. On

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24

Haas, Alois, Max Lieb, and Bernd Steffens. "Einfache Herstellung von 5-Trifluormethylthio-2′-desoxyuridin." CHIMIA 43, no. 4 (1989): 98. https://doi.org/10.2533/chimia.1989.98.

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25

Deyrup, M., R. Sidwell, R. Little, P. Druzgala, N. Bodor, and M. E. Brewster. "Improved Delivery through Biological Membranes. Synthesis and Antiviral Activity of a Series of Ribavirin Chemical Delivery Systems: 2′ and 3′ Derivatives." Antiviral Chemistry and Chemotherapy 2, no. 6 (1991): 337–55. http://dx.doi.org/10.1177/095632029100200603.

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Ribavirin was chemically manipulated to provide a number of derivatives in which a 1,4-dihydrotrigonellinate species was attached to either the 2′ or 3′-position. In addition, a variety of other modifications was used to augment the lipophilicity and stability of the ribavirin redox systems. Prepared compounds were tested in a murine model of viral encephalitis. Intravenous administration of an isomeric pair of derivatives (1-[3′-O-(N-methyl-3-carbonyl-1,4-dihydropyridine)-2′-O-benzoyl-β-D-ribofuranosyl]-1,2,4-triazole-3-carboxamide/1-[2′-O-(N-methyl-3-carbonyl-1,4-dihydropyridine)-3′-O-benzoy

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26

Kicsák, Máté, Attila Mándi, Szabolcs Varga, et al. "Tricyclanos: conformationally constrained nucleoside analogues with a new heterotricycle obtained from a d-ribofuranose unit." Organic & Biomolecular Chemistry 16, no. 3 (2018): 393–401. http://dx.doi.org/10.1039/c7ob02296d.

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Nucleoside analogues having a new N,O-containing tricycle in place of the ribose unit have been prepared by a diastereoselective cyclocondensation of Tris and dialdehydes obtained from ribofuranosyl nucleosides.

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27

Wang, Zhi-Xian, Leonard I. Wiebe, Erik De Clercq, Jan Balzarini та Edward E. Knaus. "Syntheses of 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of 2-substituted-5-fluoroaniline: "cytosine replacement" analogs of deoxycytidine for evaluation as anticancer and antihuman immunodeficiency virus (anti-HIV) agents". Canadian Journal of Chemistry 78, № 8 (2000): 1081–88. http://dx.doi.org/10.1139/v00-105.

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A group of 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of 5-fluoroaniline possessing a variety of aryl C-2 substituents (6a R = H, 6b R = F, 6c R = Me) were synthesized. Accordingly, a Heck-type coupling reaction of the 4-iodoaniline derivatives (13ac) with the bis(tert-butyldimethylsilyl)glycal (11) in the presence of Pd(OAc)2 and Ph3As, followed by removal of the tert-butyldimethylsilyl protection groups using n-Bu4N+F-, yielded the corresponding 4-(β-D-glycero-pentofuran-3-ulos-1-yl)aniline derivatives (14ac) having a C-3 C=O in the sugar ring. Reduction of the C-3 C=O compounds (14ac)

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28

Yokoyama, Masataka, Mitsuru Nomura, Hideo Togo, and Hiroko Seki. "Coupling of ribofuranosyl fluoride and indoles." Journal of the Chemical Society, Perkin Transactions 1, no. 17 (1996): 2145. http://dx.doi.org/10.1039/p19960002145.

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29

Birnbaum, K. B., D. Shugar та K. Felczak. "1-(β-D-Ribofuranosyl)-6-propylcytosine". Acta Crystallographica Section C Crystal Structure Communications 54, № 12 (1998): 1959–61. http://dx.doi.org/10.1107/s0108270198008683.

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30

Liang, Chengyi, Tianwei Ma, John S. Cooperwood, Jinfa Du, and Chung K. Chu. "Synthesis of l-ribofuranosyl C-nucleosides." Carbohydrate Research 303, no. 1 (1997): 33–38. http://dx.doi.org/10.1016/s0008-6215(97)00143-2.

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31

Bols, Mikael, Morten P. Persson, Waqas M. Butt, Martin Jørgensen, Peter Christensen, and Lars T. Hansen. "Synthesis of a ribofuranosyl cation mimic." Tetrahedron Letters 37, no. 12 (1996): 2097–100. http://dx.doi.org/10.1016/0040-4039(96)00202-x.

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32

Matulic-Adamic, Jasenka, та Leonid Beigelman. "Synthesis of 3-(β-D-ribofuranosyl)-2-fluoropyridine and 3-(β-D-ribofuranosyl)-pyridin-2-one". Tetrahedron Letters 38, № 2 (1997): 203–6. http://dx.doi.org/10.1016/s0040-4039(96)02289-7.

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33

KAPTAN, SINGH, HASAN A., PRATAP RAM, Y. GURU P., and S. BHAKUNI D. "Synthesis of 1 ,2,4-Triazolo[2,3-c]pyrimidin-5(6H)-one Nucleosides and their Antileishmanial Activity." Journal Of Indian Chemical Society Vol. 66, Aug-Oct 1989 (1989): 686–89. https://doi.org/10.5281/zenodo.6024704.

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Central Drug Research Institute, Lucknow-226 001 6-<em>ß</em>-ᴅ-Ribofuranosyl-<em>s</em>-triazolo[2,3-<em>c</em>]pyrimidin-5(6<em>H</em>)-one (5), 6-<em>ß</em>-ᴅ-xylofuranosyl-<em>s</em>-triazolo [ 2, 3-<em>c</em> ] pyrimidin-5-( 6H )-one (7), 6-(2-hydroxyethoxymethyl)- <em>s</em>-triazolo[2,3-<em>c</em>]pyrimidin-5(6<em>H</em>)-one (9) and 6-[(1,3-dihydroxy-2-propoxy) methyl]-<em>s</em>-triazolo [2,3-<em>c</em>)pyrimidin-5(6H)-one (11) have been synthesised. Compounds 2,5, 7,9 and 11 showed 70,40,65, 0 and 78% inhibition of the growth of amastigotes of <em>Leishmania don

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34

Odalo, Josiah O., Cosam C. Joseph, Mayunga H. H. Nkunya та ін. "Aristolactams, 1-(2-C-Methyl-β-D-ribofuranosyl)-uracil and Other Bioactive Constituents of Toussaintia orientalis". Natural Product Communications 5, № 2 (2010): 1934578X1000500. http://dx.doi.org/10.1177/1934578x1000500217.

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The new aristolactam alkaloid toussalactam {2-hydroxy-1,6-dimethoxy-5H-dibenzo[cdf]indol-4-one} and the known ones, namely aristolactam AII, aristolactam BII, piperolactam C and aristolactam FII; 1-(2-C-methyl-β-D-ribofuranosyl)-uracil, 3,4,5-trimethoxyphenyl-β-D-glucopyranoside, and three catechinoids were isolated from the cytotoxic Toussaintia orientalis Verdc stem and root bark extracts, and their structures established based on analysis of spectroscopic data. The aristolactams exhibited antimicrobial and antiinflammatory activity, aristolactam FII showing almost the same level of activity

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35

Zacny, Valerie L., Eduard Gershburg, Michelle G. Davis, Karen K. Biron та Joseph S. Pagano. "Inhibition of Epstein-Barr Virus Replication by a Benzimidazole l-Riboside: Novel Antiviral Mechanism of 5,6-Dichloro-2-(Isopropylamino)-1-β-l-Ribofuranosyl-1H-Benzimidazole". Journal of Virology 73, № 9 (1999): 7271–77. http://dx.doi.org/10.1128/jvi.73.9.7271-7277.1999.

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ABSTRACT Although a number of antiviral drugs inhibit replication of Epstein-Barr virus (EBV) in cell culture, and acyclovir (ACV) suppresses replication in vivo, currently available drugs have not proven effective for treatment of EBV-associated diseases other than oral hairy leukoplakia. Benzimidazole riboside compounds represent a new class of antiviral compounds that are potent inhibitors of human cytomegalovirus (HCMV) replication but not of other herpesviruses. Here we characterize the effects of two compounds in this class against lytic replication of EBV induced in a Burkitt lymphoma c

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36

Evers, David L., Gloria Komazin, Roger G. Ptak, et al. "Inhibition of Human Cytomegalovirus Replication by Benzimidazole Nucleosides Involves Three Distinct Mechanisms." Antimicrobial Agents and Chemotherapy 48, no. 10 (2004): 3918–27. http://dx.doi.org/10.1128/aac.48.10.3918-3927.2004.

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ABSTRACT The benzimidazole nucleosides 2-bromo-5,6-dichloro-1-(β-d-ribofuranosyl)benzimidazole (BDCRB) and 2-isopropylamino-5,6-dichloro-1-(β-l-ribofuranosyl)benzimidazole (1263W94, or maribavir) are potent and selective inhibitors of human cytomegalovirus (HCMV) replication. These inhibitors act by two different mechanisms: BDCRB blocks the processing and maturation of viral DNA, whereas maribavir prevents viral DNA synthesis and capsid nuclear egress. In order to determine by which of these two mechanisms other benzimidazole nucleosides acted, we performed time-of-addition studies and other

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37

Jiricny, Josef. "N6-Methoxyadenine-Pyrimidine Base Pairs as Substrates for the Mismatch Repair System of Escherichia coli." Collection of Czechoslovak Chemical Communications 66, no. 7 (2001): 1107–24. http://dx.doi.org/10.1135/cccc20011107.

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The availability of nucleoside analogues with ambiguous base-pairing properties would be of considerable value in molecular biology. We have incorporated deoxynebularine [9-(2-deoxy-β-D-ribofuranosyl)purine, P], deoxyinosine [9-(2-deoxy-β-D-ribofuranosyl)-6-hydroxypurine, I) and [9-(2-deoxy-β-D-ribofuranosyl)-6-methoxyaminopurine, MeOA] into hexadecamer oligodeoxyribonucleotides and tested their behaviour in DNA•DNA hybridisations in vitro, as well as in oligonucleotide-directed mutagenesis experiments in vivo. The results showed that P behaved as an adenine analogue in all assays. Oligonucleo

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38

Belmans, M., I. Vrijens, E. L. Esmans, et al. "Synthesis and Biological Evaluation of 3-Chloro-4-(D-Ribofuranosyl)-Pyridine and 3-(D-Ribofuranosyl)-2- Pyridone." Nucleosides and Nucleotides 6, no. 1-2 (1987): 245–48. http://dx.doi.org/10.1080/07328318708056197.

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39

Humeník, Martin, Milan Dzurilla, Peter Kutschy, Eva Solčániová, Vladimír Kováčik, and Slávka Bekešová. "Synthesis of 1-Glycosyl Derivatives of Benzocamalexin." Collection of Czechoslovak Chemical Communications 69, no. 8 (2004): 1657–74. http://dx.doi.org/10.1135/cccc20041657.

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The linear synthesis of 1-(β-D-glucopyranosyl)-, 1-(β-D-galactopyranosyl)-, 1-(β-D-mannopyranosyl)- and 1-(β-D-ribofuranosyl)benzocamalexin was elaborated from indoline as a starting compound and corresponding pentaacetylhexoses or 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribose as suitable glycosyl donors.

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40

Marfurt, J., E. Stulz, H. U. Trafelet та ін. "7-(2'-Deoxy-α-D-ribofuranosyl)hypoxanthine". Acta Crystallographica Section C Crystal Structure Communications 52, № 3 (1996): 713–16. http://dx.doi.org/10.1107/s0108270195012662.

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41

LIEBERKNECHT, A., J. SCHMIDT, and J. J. STEZOWSKI. "ChemInform Abstract: Diastereoselective Synthesis of Ribofuranosyl Glycines." ChemInform 23, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199207250.

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42

Čurillová, Zuzana, Peter Kutschy, Eva Solčániová, Martina Pilátová, Ján Mojžiš та Vladimír Kováčik. "Synthesis and antiproliferative activity of 1-methoxy-, 1-(α-D-ribofuranosyl)- and 1-(β-D-ribofuranosyl)brassenin B". Arkivoc 2008, № 8 (2008): 85–104. http://dx.doi.org/10.3998/ark.5550190.0009.809.

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43

Hřebabecký, Hubert. "Synthesis of 2-amino-5-β-D-ribofuranosyl-1,3,4-thiadiazole and 2-amino-β-D-ribofuranosyl-1,3,4-oxadiazole". Collection of Czechoslovak Chemical Communications 51, № 6 (1986): 1311–15. http://dx.doi.org/10.1135/cccc19861311.

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Benzoylated 2-amino-5-ribosylthiadiazole III and 2-amino-5-oxadiazole IV were synthesized by cyclization of allonoylthiosemicarbazide I and allonoylsemicarbazide II with phosphorus pentoxide in nitromethane. The oxadiazole IV was alternatively prepared by heating compound I with lead(II)oxide in acetonitrile. Free ribosylthiadiazole V and ribosyloxadiazole VI were obtained by methanolysis of III and IV.

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44

MATULIC-ADAMIC, J., та L. BEIGELMAN. "ChemInform Abstract: Synthesis of 3-(β-D-Ribofuranosyl)-2-fluoropyridine and 3-(β- D-Ribofuranosyl)-pyridin-2-one." ChemInform 28, № 20 (2010): no. http://dx.doi.org/10.1002/chin.199720195.

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45

Borowski, Peter, Melanie Lang, Annemarie Haag, et al. "Characterization of Imidazo[4,5-d]Pyridazine Nucleosides as Modulators of Unwinding Reaction Mediated by West Nile Virus Nucleoside Triphosphatase/Helicase: Evidence for Activity on the Level of Substrate and/or Enzyme." Antimicrobial Agents and Chemotherapy 46, no. 5 (2002): 1231–39. http://dx.doi.org/10.1128/aac.46.5.1231-1239.2002.

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ABSTRACT Compounds that interact with DNA or RNA generally act as inhibitors of enzymes that unwind DNA or RNA. In the present study we describe the synthesis and properties of some nucleoside analogues that interact with double-stranded DNA but that, in contrast, facilitate the unwinding reaction mediated by West Nile (WN) virus nucleoside triphosphatase (NTPase)/helicase. The nucleoside analogues described, 1-(2′-O-methyl-β-d-ribofuranosyl)imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione (HMC-HO4), 1-(β-d-ribofuranosyl)imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione, and 1-(2′-deoxy-α-d-ribofuranosyl)imi

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46

Hwang, Jae-Seon, Oliver Kregler, Rita Schilf, et al. "Identification of Acetylated, Tetrahalogenated Benzimidazole d-Ribonucleosides with Enhanced Activity against Human Cytomegalovirus." Journal of Virology 81, no. 21 (2007): 11604–11. http://dx.doi.org/10.1128/jvi.01130-07.

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ABSTRACT DNA packaging is the key step in viral maturation and involves binding and cleavage of viral DNA containing specific DNA-packaging motifs. This process is mediated by a group of specific enzymes called terminases. We previously demonstrated that the human cytomegalovirus (HCMV) terminase is composed of the large subunit pUL56 and the small subunit pUL89. While the large subunit mediates sequence-specific DNA binding and ATP hydrolysis, pUL89 is required only for duplex nicking. An excellent inhibitor targeting HCMV terminase is 2-bromo-5,6-dichloro-1-(β-d-ribofuranosyl)benzimidazole (

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47

Koole, Leo H., Henk M. Buck, Agnes Nyilas, and Jyoti Chattopadhyaya. "Structural properties of modified deoxyadenosine structures in solution. Impact of the gauche and anomeric effects on the furanose conformation." Canadian Journal of Chemistry 65, no. 9 (1987): 2089–94. http://dx.doi.org/10.1139/v87-346.

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A variable temperature high resolution 1H nuclear magnetic resonance study (at 300 or 500 MHz) of the two modified nucleosides 9-(2′-deoxy-β-D-threo-ribofuranosyl)-adenine (1) and 9-(3′-deoxy-β-D-threo-ribofuranosyl)-adenine (2) has been performed. It was found that the furanose conformation in 1 and 2 can be best described as a rapid North (N) [Formula: see text] South (S) equilibrium that is biased toward the N-form. For 1, a marked temperature dependence of the [Formula: see text] equilibrium was found, whereas the furanose conformation in 2 is virtually insensitive to temperature changes.

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48

Hanna, Naeem B., Milena Masojídková, and Alois Pískala. "Synthesis and Biological Activity of N4-Methyl-5-azacytidines." Collection of Czechoslovak Chemical Communications 63, no. 5 (1998): 713–22. http://dx.doi.org/10.1135/cccc19980713.

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Protected N4-methyl and N4,N4-dimethyl derivatives of 5-azacytidine 3 and 4 were prepared by selective aminolysis of benzoylated 4-methoxy-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one 5, by glycosylation of silylated N4-methyl- or N4,N4-dimethyl-5-azacytosines 7 and 8 with 2,3,5-tri-O-benzoyl-α,β-D-ribofuranosyl chloride (11) or by several modifications of the isocyanate method. By the isocyanate approach, also the α-D anomer of protected N4-methyl-5-azacytidine 17 was obtained as a minor product. The protected dimethyl derivative 4 was also obtained by the reaction of isobiuret 22 with dimet

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49

Fathi, Reza, and Frank Jordan. "Certain novel ribofuranosyl phosphates derived from 5-phospho-.alpha.-D-ribofuranosyl-1-pyrophosphate: synthesis, structure, and alkaline hydrolytic reactivities." Journal of Organic Chemistry 53, no. 9 (1988): 1997–2001. http://dx.doi.org/10.1021/jo00244a028.

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Iaroshenko, Viktor O., Sergii Dudkin, Vyacheslav Ya Sosnovskikh, Alexander Villinger та Peter Langer. "(β-D-Ribofuranosyl)formamidine in the Design and Synthesis of 2-(β-D-Ribofuranosyl)pyrimidines, Including RF-Containing Derivatives". European Journal of Organic Chemistry 2013, № 15 (2013): 3166–73. http://dx.doi.org/10.1002/ejoc.201300107.

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