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Journal articles on the topic 'C-nucleoside'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

Maeba, Isamu, Masakazu Wakimura, Yasutaka Ito, and Chihiro Ito. "C-Nucleosides. 22. Synthesis of Quinoxaline Acyclo-C-nucleoside." HETEROCYCLES 36, no. 11 (1993): 2591. http://dx.doi.org/10.3987/com-93-6501.

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2

Rondla, Ramu, Steven J. Coats, Tamara R. McBrayer та ін. "Anti-hepatitis C Virus Activity of Novel β-D-2′-C-methyl-4′-azido Pyrimidine Nucleoside Phosphoramidate Prodrugs". Antiviral Chemistry and Chemotherapy 20, № 2 (2009): 99–106. http://dx.doi.org/10.3851/imp1400.

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Background: 2′- C-methyl and 4′-azido nucleosides have previously demonstrated inhibition of hepatitis C virus (HCV) replication by targeting the RNA-dependent RNA polymerase NS5B. In an effort to discover new and more potent anti-HCV agents, we envisioned synthesizing nucleoside analogues by combining the 2′- C-methylmoiety with the 4′-azido-moiety into one molecule. Methods: 2′- C-methyl-4′-azido pyrimidine nucleosides were synthesized by first converting 2′- C-methyl ribonucleosides to the corresponding 4′-exocyclic methylene nucleosides. Treatment with iodine azide, benzoylation of the 2′-

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3

Kaczmarek, Renata, Dariusz Korczyński, James R. Green, and Roman Dembinski. "Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction." Beilstein Journal of Organic Chemistry 16 (January 2, 2020): 1–8. http://dx.doi.org/10.3762/bjoc.16.1.

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Dicobalt hexacarbonyl nucleoside complexes of propargyl ether or esters of 5-substituted uridines react with diverse C-nucleophiles. Synthetic outcomes confirmed that the Nicholas reaction can be carried out in a nucleoside presence, leading to a divergent synthesis of novel metallo-nucleosides enriched with alkene, arene, arylketo, and heterocyclic functions, in the deoxy and ribo series.

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4

MAEBA, I., M. WAKIMURA, Y. ITO, and C. ITO. "ChemInform Abstract: C-Nucleosides. Part 22. Synthesis of Quinoxaline Acyclo-C-Nucleoside." ChemInform 25, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199411183.

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5

Hassan, Mohamed Ezeldin. "Palladium-catalyzed cross-coupling reaction of organostannanes with nucleoside halides." Collection of Czechoslovak Chemical Communications 56, no. 9 (1991): 1944–47. http://dx.doi.org/10.1135/cccc19911944.

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A general reaction is described for the synthesis of C-5 substituted nucleosides through the coupling of organostannanes with nucleoside-palladium intermediate derived in situ from 5-iodouridine (or 5-iodo-2’-deoxyuridine) and [PdCl2(PPh3)2]. The reaction was used for the synthesis of C-5 aryl, heteroaryl, vinyl, allyl and alkyl substituted nucleosides.

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6

Grouiller, Annie, and Hassan Essadiq. "Behaviour of 2′-O-p-toluenesulfonyl uridine towards excess of a Grignard reagent." Canadian Journal of Chemistry 67, no. 4 (1989): 708–9. http://dx.doi.org/10.1139/v89-108.

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Two C-methylated base nucleosides were obtained when 2′-O-tosyl-5′-O-trityluridine was reacted with 30 equivalents of methylmagnesium iodide. Keywords: nucleoside, Grignard reaction, C-methyl pyrimidinone, anhydro derivative, arabinofuranosyl.

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7

Iwasaki, Hiromichi, Peng Huang, Michael J. Keating, and William Plunkett. "Differential Incorporation of Ara-C, Gemcitabine, and Fludarabine Into Replicating and Repairing DNA in Proliferating Human Leukemia Cells." Blood 90, no. 1 (1997): 270–78. http://dx.doi.org/10.1182/blood.v90.1.270.

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Abstract The major actions of nucleoside analogs such as arabinosylcytosine (ara-C) and fludarabine occurs after their incorporation into DNA, during either replication or repair synthesis. The metabolic salvage and DNA incorporation of the normal nucleoside, deoxycytidine, is functionally compartmentalized toward repair synthesis in a process regulated by ribonucleotide reductase. The aim of this study was to investigate the metabolic pathways by which nucleoside analogs that do (fludarabine, gemcitabine) or do not (ara-C) affect ribonucleotide reductase are incorporated into DNA in prolifera

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8

Iwasaki, Hiromichi, Peng Huang, Michael J. Keating, and William Plunkett. "Differential Incorporation of Ara-C, Gemcitabine, and Fludarabine Into Replicating and Repairing DNA in Proliferating Human Leukemia Cells." Blood 90, no. 1 (1997): 270–78. http://dx.doi.org/10.1182/blood.v90.1.270.270_270_278.

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The major actions of nucleoside analogs such as arabinosylcytosine (ara-C) and fludarabine occurs after their incorporation into DNA, during either replication or repair synthesis. The metabolic salvage and DNA incorporation of the normal nucleoside, deoxycytidine, is functionally compartmentalized toward repair synthesis in a process regulated by ribonucleotide reductase. The aim of this study was to investigate the metabolic pathways by which nucleoside analogs that do (fludarabine, gemcitabine) or do not (ara-C) affect ribonucleotide reductase are incorporated into DNA in proliferating huma

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9

Ogawa, Jun, Sou Takeda, Sheng-Xue Xie, et al. "Purification, Characterization, and Gene Cloning of Purine Nucleosidase from Ochrobactrum anthropi." Applied and Environmental Microbiology 67, no. 4 (2001): 1783–87. http://dx.doi.org/10.1128/aem.67.4.1783-1787.2001.

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ABSTRACT A bacterium, Ochrobactrum anthropi, produced a large amount of a nucleosidase when cultivated with purine nucleosides. The nucleosidase was purified to homogeneity. The enzyme has a molecular weight of about 170,000 and consists of four identical subunits. It specifically catalyzes the irreversibleN-riboside hydrolysis of purine nucleosides, theKm values being 11.8 to 56.3 μM. The optimal activity temperature and pH were 50°C and pH 4.5 to 6.5, respectively. Pyrimidine nucleosides, purine and pyrimidine nucleotides, NAD, NADP, and nicotinamide mononucleotide are not hydrolyzed by the

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10

Kryczka, Tomasz, Maciej Bero, Janusz Kasperczyk, et al. "In vitro release of cytotoxic nucleoside analogs from lactide-caprolactone and lactide-glycolide copolymers." Acta Biochimica Polonica 49, no. 1 (2002): 205–10. http://dx.doi.org/10.18388/abp.2002_3837.

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The aims of our study were to assess the release of cytotoxic nucleoside analogs 5-fluorouracil and 2-chloro-2'-deoxyadenosine from different lactide-glycolide or lactide-caprolactone biodegradable copolymers and the effects of sterilization on this release. The polymers were sterilized either with ethylene oxide at 37 degrees C, or with gamma radiation (15 kGy, 20 kGy, or 25 kGy). The kinetics of nucleoside release from the copolymers were measured over 50 days. Four copolymers exhibited relatively constant release of nucleosides in micromolar concentrations during the entire observation peri

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11

Cermola, Flavio, Serena Vella, Marina DellaGreca, Angela Tuzi, and Maria Rosaria Iesce. "A One-Pot Approach to Novel Pyridazine C-Nucleosides." Molecules 26, no. 8 (2021): 2341. http://dx.doi.org/10.3390/molecules26082341.

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The synthesis of glycosides and modified nucleosides represents a wide research field in organic chemistry. The classical methodology is based on coupling reactions between a glycosyl donor and an acceptor. An alternative strategy for new C-nucleosides is used in this approach, which consists of modifying a pre-existent furyl aglycone. This approach is applied to obtain novel pyridazine C-nucleosides starting with 2- and 3-(ribofuranosyl)furans. It is based on singlet oxygen [4+2] cycloaddition followed by reduction and hydrazine cyclization under neutral conditions. The mild three-step one-po

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12

Hassan, Mohamed Ezeldin. "A new palladium-catalyzed coupling reaction of vinylic and allylic triflates with pyrimidine nucleosides." Canadian Journal of Chemistry 69, no. 2 (1991): 198–200. http://dx.doi.org/10.1139/v91-031.

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Vinylic trifluoromethane sulfonates (triflates) form palladium intermediates that react with pyrimidine nucleosides to produce C-5 alkyl substituted nucleosides after hydrogenation of the vinylic coupling products with hydrogen and Pd/C in methanol. The reaction, which is run under mild conditions, appears to be a general one since both mono- and disubstituted vinylic triflates, as well as the cyclic ones, gave high yields of the corresponding C-5 alkyl-substituted nucleoside. The reaction with allyl triflate requires the use of the 5-chloromercurinucleoside. Key words: nucleosides, triflates,

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13

Maeba, Isamu, Yasutaka Ito, Masakazu Wakimura, and Chihiro Ito. "C-Nucleosides. 21. Synthesis of Isoxazole C-Nucleoside from Furanone Glycoside via Enaminone Glycoside." HETEROCYCLES 36, no. 7 (1993): 1617. http://dx.doi.org/10.3987/com-93-6370.

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14

Bergstrom, Don, Xiaoping Lin, Guangyi Wang, et al. "C-5-Substituted Nucleoside Analogs." Synlett 1992, no. 03 (1992): 179–88. http://dx.doi.org/10.1055/s-1992-21307.

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15

Dolinar, Klemen, Vid Jan, Mojca Pavlin, Alexander V. Chibalin, and Sergej Pirkmajer. "Nucleosides block AICAR-stimulated activation of AMPK in skeletal muscle and cancer cells." American Journal of Physiology-Cell Physiology 315, no. 6 (2018): C803—C817. http://dx.doi.org/10.1152/ajpcell.00311.2017.

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AMP-activated kinase (AMPK) is a major regulator of energy metabolism and a promising target for development of new treatments for type 2 diabetes and cancer. 5-Aminoimidazole-4-carboxamide-1-β-d-ribofuranoside (AICAR), an adenosine analog, is a standard positive control for AMPK activation in cell-based assays. Some broadly used cell culture media, such as minimal essential medium α (MEMα), contain high concentrations of adenosine and other nucleosides. We determined whether such media alter AICAR action in skeletal muscle and cancer cells. In nucleoside-free media, AICAR stimulated AMPK acti

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16

Lundgren, Hans K., and Glenn R. Björk. "Structural Alterations of the Cysteine Desulfurase IscS of Salmonella enterica Serovar Typhimurium Reveal Substrate Specificity of IscS in tRNA Thiolation." Journal of Bacteriology 188, no. 8 (2006): 3052–62. http://dx.doi.org/10.1128/jb.188.8.3052-3062.2006.

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ABSTRACT The cysteine desulfurase IscS in Salmonella enterica serovar Typhimurium is required for the formation of all four thiolated nucleosides in tRNA, which is thought to occur via two principally different biosynthetic pathways. The synthesis of 4-thiouridine (s4U) and 5-methylaminomethyl-2-thiouridine (mnm5s2U) occurs by a transfer of sulfur from IscS via various proteins to the target nucleoside in the tRNA, and no iron-sulfur cluster protein participates, whereas the synthesis of 2-thiocytidine (s2C) and N 6-(4-hydroxyisopentenyl)-2-methylthioadenosine (ms2io6A) is dependent on iron-su

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17

Ritzel, M. W., S. Y. Yao, M. Y. Huang, J. F. Elliott, C. E. Cass, and J. D. Young. "Molecular cloning and functional expression of cDNAs encoding a human Na+-nucleoside cotransporter (hCNT1)." American Journal of Physiology-Cell Physiology 272, no. 2 (1997): C707—C714. http://dx.doi.org/10.1152/ajpcell.1997.272.2.c707.

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We report identification of a new human nucleoside transporter protein by molecular cloning and functional expression of its cDNA. Previously, we used expression selection in Xenopus oocytes to isolate a cDNA from rat jejunal epithelium encoding the pyrimidine-selective Na+-dependent nucleoside transporter rCNT1 (Q.-Q. Huang, S. Y. M. Yao, M. W. L. Ritzel, A. R. P. Paterson, C. E. Cass, and J. D. Young. J. Biol. Chem. 269: 17757-17760, 1994). cDNAs for a human homologue of rCNT1, designated hCNT1, have been isolated from human kidney by hybridization cloning and reverse transcriptase polymeras

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18

Griffon, Jean-François, Sue C. Shaddix, William B. Parker та ін. "Synthesis and Biological Evaluation of Some 4'-C-(Hydroxymethyl)-α- and -β-D-Arabinofuranosyl Pyrimidine and Adenine Nucleosides". Collection of Czechoslovak Chemical Communications 71, № 7 (2006): 1063–87. http://dx.doi.org/10.1135/cccc20061063.

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A series of 4'-C-(hydroxymethyl) analogs of pyrimidine and purine nucleosides have been prepared utilizing standard methodologies, and the α and β anomers were separated. These analogs are part of our continuing efforts to identify new anticancer drugs as well as to explore the substrate specificities of these analogs with the initial activating enzymes in the metabolic pathway leading to nucleoside triphosphates. Although not cytotoxic to CCRF-CEM cells (an acute lymphoblastic leukemia of T-cell origin), many of these compounds were utilized as substrates for the various human nucleoside kina

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19

Bhilare, Shatrughn, Harshita Shet, Yogesh S. Sanghvi, and Anant R. Kapdi. "Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes." Molecules 25, no. 7 (2020): 1645. http://dx.doi.org/10.3390/molecules25071645.

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Nucleic acid derivatives are imperative biomolecules and are involved in life governing processes. The chemical modification of nucleic acid is a fascinating area for researchers due to the potential activity exhibited as antiviral and antitumor agents. In addition, these molecules are also of interest toward conducting useful biochemical, pharmaceutical, and mutagenic study. For accessing such synthetically useful structures and features, transition-metal catalyzed processes have been proven over the years to be an excellent tool for carrying out the various transformations with ease and unde

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20

Wang, Guangyi, and Esmir Gunic. "Conformationally Locked Nucleoside Analogs. Synthesis of 2′-Deoxy-2′-C, 4′-C-Bridged Bicyclic Nucleosides." Nucleosides and Nucleotides 18, no. 4-5 (1999): 531–36. http://dx.doi.org/10.1080/15257779908041488.

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21

Mehta, Kamal D., and Radhey S. Gupta. "Chinese hamster ovary cell mutants specifically affected in the phosphorylation of C-purine nucleosides." Canadian Journal of Biochemistry and Cell Biology 63, no. 9 (1985): 1044–48. http://dx.doi.org/10.1139/o85-129.

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In Chinese hamster ovary cells, two different types of mutants resistant to purine nucleoside analogs have been isolated. One type of mutants selected in presence of C-nucleosides formycin A and formycin B (FomR mutants) exhibited a high degree of cross resistance to different C-nucleosides but showed very slight to no cross resistance to various N-nucleosides. In contrast, mutants selected in presence of toyocamycin (Toyr mutants) exhibited a high degree of cross resistance to all C- and N-adenosine analogs. Studies on the cellular uptake and phosphorylation of [3H]adenosine, [3H]tubercidin,

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22

Yamaguchi, K., Y. Ito, K. Haraguchi, H. Tanaka, and T. Miyasaka. "A 1'-C-branched uracil nucleoside." Acta Crystallographica Section C Crystal Structure Communications 50, no. 9 (1994): 1472–74. http://dx.doi.org/10.1107/s0108270194001022.

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23

Ané, A., G. Prestat, G. T. Manh, et al. "Synthesis of nucleoside analogs and new Tat protein inhibitors." Pure and Applied Chemistry 73, no. 7 (2001): 1189–96. http://dx.doi.org/10.1351/pac200173071189.

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Two studies, concerning the synthesis of original nucleoside analogs regarded as an application of heterochemistry on thiaazaheterocycle systems from thiaazabutadienes are discussed. The preparation of new N- and C-nucleosides is presented. In the second part, the discovery of aromatic polycyclic derivatives as inhibitors of Tat protein is exposed. The work presented takes into account the participation of African partners in further synthetic research programs carried out in collaboration with the laboratory of Nantes.

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24

Seitz, Gunther, and Johanna Siegl. "Synthese neuer Pyridin-C-nukleoside der 2 ,3 -Didesoxyribose durch „inverse“ [4+2]-Cycloaddition Synthesis of Novel Pyridine-C-nucleosides of 2,3-Dideoxyribose by „Inverse“ [4+2]-Cycloaddition." Zeitschrift für Naturforschung B 52, no. 7 (1997): 851–58. http://dx.doi.org/10.1515/znb-1997-0715.

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The anomeric imido esters 5 and 6, appropriate precursors for C-nucleoside synthesis, were prepared and utilized as heterodienophiles in a Diels-Alder reaction with inverse electron demand to yield the novel, protected 1.2.4-triazine C-nucleosides 8 and 9. They could be deprotected by treatment with 70% trifluoroacetic acid to furnish the free C-nucleosides 10 and 11. The triazine „aglycon“ of 8 contains an electron deficient diazadiene system, highly activated to react with various electron rich dienophiles such as enamines, enol ethers and several cyclic ketene acetals in an „inverse“ [4+2]-

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25

Rajwanshi, Vivek K., Ravindra Kumar, Mikael Kofod-Hansen, and Jesper Wengel. "Synthesis and restricted furanose conformations of three novel bicyclic thymine nucleosides: a xylo-LNA nucleoside, a 3′-O,5′-C-methylene-linked nucleoside, and a 2′-O,5′-C-methylene-linked nucleoside." Journal of the Chemical Society, Perkin Transactions 1, no. 11 (1999): 1407–14. http://dx.doi.org/10.1039/a901729a.

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26

Bhattacharya, Birendra K., Mu-Ill Lim, Brian A. Otter, and Robert S. Klein. "Synthesis of furo[3,2-]pyrimidine nucleosides: A novel c-nucleoside isostere of adenosine." Tetrahedron Letters 27, no. 7 (1986): 815–18. http://dx.doi.org/10.1016/s0040-4039(00)84108-8.

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27

Barbato, Stefania, Gennaro Piccialli, Ciro Santacroce, Lorenzo De Napoli, and Luciano Mayol. "Synthesis of Bridged Pyrimidine Nucleosides and Triazo [4, 3-c] Pyrimidine Nucleoside Analogues." Nucleosides and Nucleotides 8, no. 4 (1989): 515–28. http://dx.doi.org/10.1080/07328318908054194.

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28

Barbato, Stefania, Gennaro Piccialli, Ciro Santacroce, Lorenzo De Napoli, and Luciano Mayol. "Synthesis of Bridged Pyrimidine Nucleosides and Triazo [4, 3-c] Pyrimidine Nucleoside Analogues." Nucleosides and Nucleotides 10, no. 4 (1991): 853–66. http://dx.doi.org/10.1080/07328319108046666.

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29

Kasthuri, Mahesh, Chengwei Li, Kiran Verma та ін. "Synthesis of 4′-Substituted-2′-Deoxy-2′-α-Fluoro Nucleoside Analogs as Potential Antiviral Agents". Molecules 25, № 6 (2020): 1258. http://dx.doi.org/10.3390/molecules25061258.

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Nucleoside analogs are widely used for the treatment of viral diseases (Hepatitis B/C, herpes and human immunodeficiency virus, HIV) and various malignancies. ALS-8176, a prodrug of the 4′-chloromethyl-2′-deoxy-2′-fluoro nucleoside ALS-8112, was evaluated in hospitalized infants for the treatment of respiratory syncytial virus (RSV), but was abandoned for unclear reasons. Based on the structure of ALS-8112, a series of novel 4′-modified-2′-deoxy-2′-fluoro nucleosides were synthesized. Newly prepared compounds were evaluated against RSV, but also against a panel of RNA viruses, including Dengue

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30

MAEBA, I., Y. ITO, M. WAKIMURA, and C. ITO. "ChemInform Abstract: C-Nucleosides. Part 21. Synthesis of Isoxazole C-Nucleoside from Furanone Glycoside via Enaminone Glycoside." ChemInform 24, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.199339289.

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31

Wang, G., and Esmir Gunic. "ChemInform Abstract: Conformationally Locked Nucleoside Analogues. Synthesis of 2′-Deoxy-2′-C, 4′-C-Bridged Bicyclic Nucleosides." ChemInform 30, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199941204.

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32

Franchetti, Palmarisa, Stefano Marchetti, Loredana Cappellacci, et al. "A new C-nucleoside analogue of tiazofurin." Bioorganic & Medicinal Chemistry Letters 11, no. 1 (2001): 67–69. http://dx.doi.org/10.1016/s0960-894x(00)00594-1.

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33

Cai, Dongmei, Kunhua Lin, Maoping Song, and Tianpa You. "Ring‐Expanded C‐Nucleoside Analogues of Tiazofurin." Synthetic Communications 34, no. 1 (2004): 159–70. http://dx.doi.org/10.1081/scc-120027249.

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34

BERGSTROM, D., X. LIN, G. WANG, et al. "ChemInform Abstract: C-5-Substituted Nucleoside Analogs." ChemInform 23, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199237331.

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35

Nie, Peng, Elisabetta Groaz, and Piet Herdewijn. "Synthesis of a Threosyl-C-nucleoside Phosphonate." European Journal of Organic Chemistry 2019, no. 39 (2019): 6666–72. http://dx.doi.org/10.1002/ejoc.201901200.

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36

Pankiewicz, Krzysztof W., Marek M. Kabat, Elzbieta Sochacka, Lech Ciszewski, Joanna Zeidler, and Kyoichi A. Watanabe. "C-Nucleoside Analogues of Nicotinamide Mononucleotide (NMN)." Nucleosides and Nucleotides 7, no. 5-6 (1988): 589–93. http://dx.doi.org/10.1080/07328318808056291.

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37

Rajwanshi, Vivek K., Ravindra Kumar, Mikael Kofod-Hansen, and Jesper Wengel. "ChemInform Abstract: Synthesis and Restricted Furanose Conformations of Three Novel Bicyclic Thymine Nucleosides: A xylo-LNA Nucleoside, a 3′-O,5′-C-Methylene-Linked Nucleoside, and a 2′-O,5′-C-Methylene-Linked Nucleoside." ChemInform 30, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199937247.

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38

Maeba, Isamu, Yasufumi Nishiyama, Shigeyuki Kanazawa, and Akiko Sato. "C-Nucleosides. 24. Synthesis of Pyrazolo[1,5-a]pyrimidine C-Nucleoside through Cyclocondensation of Enaminone Glycoside with Aminopyrazoles." HETEROCYCLES 41, no. 3 (1995): 507. http://dx.doi.org/10.3987/com-94-6972.

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39

Bassetto, Marcella, Cecilia M. Cima, Mattia Basso, et al. "Novel Nucleoside Analogues as Effective Antiviral Agents for Zika Virus Infections." Molecules 25, no. 20 (2020): 4813. http://dx.doi.org/10.3390/molecules25204813.

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Previously considered a neglected flavivirus, Zika virus has recently emerged as a public health concern due to its ability to spread rapidly and cause severe neurological disorders, such as microcephaly in newborn babies from infected mothers, and Guillain-Barré syndrome in adults. Despite extensive efforts towards the identification of effective therapies, specific antivirals are still not available. As part of ongoing medicinal chemistry studies to identify new antiviral agents, we screened against Zika virus replication in vitro in a targeted internal library of small-molecule agents, comp

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40

Rodriguez, Juan B., Victor E. Marquez, Marc C. Nicklaus, Hiroaki Mitsuya, and Joseph J. Barchi. "Conformationally Locked Nucleoside Analogs. Synthesis of Dideoxycarbocyclic Nucleoside Analogs Structurally Related to Neplanocin C." Journal of Medicinal Chemistry 37, no. 20 (1994): 3389–99. http://dx.doi.org/10.1021/jm00046a024.

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41

Coelmont, Lotte, Jan Paeshuyse, Marc P. Windisch, Erik De Clercq, Ralf Bartenschlager, and Johan Neyts. "Ribavirin Antagonizes the In Vitro Anti-Hepatitis C Virus Activity of 2′-C-Methylcytidine, the Active Component of Valopicitabine." Antimicrobial Agents and Chemotherapy 50, no. 10 (2006): 3444–46. http://dx.doi.org/10.1128/aac.00372-06.

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ABSTRACT Ribavirin antagonizes the in vitro anti-hepatitis C virus (HCV) activity of the pyrimidine nucleoside analogue 2′-C-methylcytidine, the active component of the experimental anti-HCV drug valopicitabine. In contrast, the combination of ribavirin with either the purine nucleoside analogue 2′-C-methyladenosine or the HCV protease inhibitor VX-950 resulted in an additive antiviral activity. These findings may have implications when planning clinical studies with valopicitabine.

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42

PAOLI, Paolo, Guido CAMICI, Giampaolo MANAO, Elisa GIANNONI, and Giampietro RAMPONI. "Acylphosphatase possesses nucleoside triphosphatase and nucleoside diphosphatase activities." Biochemical Journal 349, no. 1 (2000): 43–49. http://dx.doi.org/10.1042/bj3490043.

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We have demonstrated that acylphosphatase possesses ATP-diphosphohydrolase (apyrase-like) activity. In fact, acylphosphatase first catalyses the hydrolysis of the γ-phosphate group of nucleoside triphosphates, and then attacks the β-phosphate group of the initially produced nucleoside diphosphates, generating nucleoside monophosphates. In constrast, it binds nucleoside monophosphates but does not catalyse their hydrolyses. The calculated kcat values for the nucleoside triphosphatase activity of acylphosphatase are of the same order of magnitude as those displayed by certain G-proteins. An acid

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43

Tecle, Eillen, Crystal B. Chhan, Latisha Franklin, Ryan S. Underwood, Wendy Hanna-Rose, and Emily R. Troemel. "The purine nucleoside phosphorylase pnp-1 regulates epithelial cell resistance to infection in C. elegans." PLOS Pathogens 17, no. 4 (2021): e1009350. http://dx.doi.org/10.1371/journal.ppat.1009350.

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Intestinal epithelial cells are subject to attack by a diverse array of microbes, including intracellular as well as extracellular pathogens. While defense in epithelial cells can be triggered by pattern recognition receptor-mediated detection of microbe-associated molecular patterns, there is much to be learned about how they sense infection via perturbations of host physiology, which often occur during infection. A recently described host defense response in the nematode C. elegans called the Intracellular Pathogen Response (IPR) can be triggered by infection with diverse natural intracellul

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44

Csuk, René, Petra Dörr, Martin Kühn, et al. "Chiral Pool Synthesis of 4a-Substituted Carbocyclic Cyclopentanoid Nucleoside Precursors, II." Zeitschrift für Naturforschung B 54, no. 8 (1999): 1079–91. http://dx.doi.org/10.1515/znb-1999-0817.

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Suitable protected 4,4a-anhydro-cyclopentane derivatives have been used for the straightforward of cyclopentanoid nucleoside precursors. Thus, by simple transformations nucleoside precursors modified at the positions C(4), C(4a) and C(4,4a) as well as side-chain modified derivatives were accessible. The structures of the key intermediates were determined by xray analyses.

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Cosson, Fanny, Aline Faroux, Jean-Pierre Baltaze, et al. "Synthesis of ribavirin 2’-Me-C-nucleoside analogues." Beilstein Journal of Organic Chemistry 13 (April 21, 2017): 755–61. http://dx.doi.org/10.3762/bjoc.13.74.

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An efficient synthetic pathway leading to two carbonated analogues of ribavirin is described. The key-steps in the synthesis of these ribosyltriazoles bearing a quaternary carbon atom in the 2’-position are an indium-mediated alkynylation and a 1,3-dipolar cyclization.

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46

Carroll, S., and D. Olsen. "Nucleoside Analog Inhibitors of Hepatitis C Virus Replication." Infectious Disorders - Drug Targets 6, no. 1 (2006): 17–29. http://dx.doi.org/10.2174/187152606776056698.

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YAMAGUCHI, K., Y. ITO, K. HARAGUCHI, H. TANAKA, and T. MIYASAKA. "ChemInform Abstract: A 1′-C-Branched Uracil Nucleoside." ChemInform 26, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199511272.

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KRECMEROVA, M. "ChemInform Abstract: C-Alkylation of Heterocyclic Nucleoside Bases." ChemInform 22, no. 12 (2010): no. http://dx.doi.org/10.1002/chin.199112357.

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Alexandrova, L. A. "4′-C-nucleoside derivatives: Synthesis and antiviral properties." Russian Journal of Bioorganic Chemistry 37, no. 6 (2011): 651–71. http://dx.doi.org/10.1134/s1068162011060021.

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Sofia, Michael J., Wonsuk Chang, Phillip A. Furman, Ralph T. Mosley, and Bruce S. Ross. "Nucleoside, Nucleotide, and Non-Nucleoside Inhibitors of Hepatitis C Virus NS5B RNA-Dependent RNA-Polymerase." Journal of Medicinal Chemistry 55, no. 6 (2012): 2481–531. http://dx.doi.org/10.1021/jm201384j.

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