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Journal articles on the topic 'Nucleosides Antiviral nucleosides'

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Published: 4 June 2021

Last updated: 4 February 2022

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1

Robins, Morris J., Danuta Madej, Fritz Hansske та ін. "Nucleic acid related compounds. 53. Synthesis and biological evaluation of 2′-deoxy-β-threo-pentofuranosyl nucleosides. "Reversion to starting alcohol" in Barton-type reductions of thionocarbonates". Canadian Journal of Chemistry 66, № 5 (1988): 1258–62. http://dx.doi.org/10.1139/v88-204.

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Treatment of selectively 3′,5′-protected β-D-xylofuranosyl nucleosides (4) with phenyl chlorothionocarbonate and DMAP followed by hydrogenolysis of the resulting (2′-O-phenoxythiocarbonyl) phenyl thionocarbonate esters (6) with tributylstannane/AIBN, and deprotection, gave 2′-deoxy-β-D-threo-pentofuranosyl nucleosides (7). Formation of a by-product bis(nucleosid-2′-yl)thionocarbonate dimer (8) was detected in the uracil nucleoside reaction sequence. Its subsequent reduction provides one explanation for "reversion to starting alcohol" in Barton-type deoxygenation reactions. Only the guanine 2′-

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2

Shi, Junxing, Judy S. Mathew, Phillip M. Tharnish, et al. "N4-Acyl-Modified D-2′,3′-Dideoxy-5-Fluorocytidine Nucleoside Analogues with Improved Antiviral Activity." Antiviral Chemistry and Chemotherapy 14, no. 2 (2003): 81–90. http://dx.doi.org/10.1177/095632020301400203.

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A series of 2,3-dideoxy (D2) and 2,3-didehydro-2,3-dideoxy (D4) 5-fluorocytosine nucleosides modified with substituted benzoyl, heteroaromatic carbonyl, cycloalkylcarbonyl and alkanoyl at the N4-position were synthesized and evaluated for anti-human immunodeficiency virus type 1 (HIV-1) and anti-hepatitis B virus (HBV) activity in vitro. For most D2-nucleosides, N4-substitutions improved the anti-HIV-1 activity markedly without increasing the cytotoxicity. In the D4-nucleosides series, some of the substituents at the N4-position enhanced the anti-HIV-1 activity with a modest increase in the cy

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3

Wiebe, Leonard, Edward Knaus, A. Majid Cheraghali, Rakesh Kumar, Kevin Morin, and L. Wang. "5-Halo-6-alkoxy-5,6-dihydro-pyrimidine Nucleosides: Antiviral Nucleosides or Nucleoside Prodrugs?" Nucleosides, Nucleotides and Nucleic Acids 14, no. 3 (1995): 501–5. http://dx.doi.org/10.1080/15257779508012413.

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4

Choo, Hyunah, James R. Beadle, Earl R. Kern, et al. "Antiviral Activities of Novel 5-Phosphono-Pent-2-en-1-yl Nucleosides and Their Alkoxyalkyl Phosphonoesters." Antimicrobial Agents and Chemotherapy 51, no. 2 (2006): 611–15. http://dx.doi.org/10.1128/aac.00444-06.

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ABSTRACT Three acyclic nucleoside phosphonates are currently approved for clinical use against infections caused by cytomegalovirus (Vistide), hepatitis B virus (Hepsera), and human immunodeficiency virus type 1 (Viread). This important antiviral class inhibits viral polymerases after cellular uptake and conversion to their diphosphates, bypassing the first phosphorylation, which is required for conventional nucleoside antivirals. Small chemical alterations in the acyclic side chain lead to marked differences in antiviral activity and the spectrum of activity of acyclic nucleoside phosphonates

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5

Young, James D. "The SLC28 (CNT) and SLC29 (ENT) nucleoside transporter families: a 30-year collaborative odyssey." Biochemical Society Transactions 44, no. 3 (2016): 869–76. http://dx.doi.org/10.1042/bst20160038.

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Specialized nucleoside transporter (NT) proteins are required for passage of nucleosides and hydrophilic nucleoside analogues across biological membranes. Physiologic nucleosides serve as central salvage metabolites in nucleotide biosynthesis, and nucleoside analogues are used as chemotherapeutic agents in the treatment of cancer and antiviral diseases. The nucleoside adenosine modulates numerous cellular events via purino-receptor cell signalling pathways. Human NTs are divided into two structurally unrelated protein families: the SLC28 concentrative nucleoside transporter (CNT) family and th

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6

Seley-Radtke, Katherine. "Flexibility—Not just for yoga anymore!" Antiviral Chemistry and Chemotherapy 26 (January 2018): 204020661875678. http://dx.doi.org/10.1177/2040206618756788.

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Over the past few years, nucleosides have maintained a prominent role as one of the cornerstones of antiviral and anticancer therapeutics, and many approaches to nucleoside drug design have been pursued. One such approach involves flexibility in the sugar moiety of nucleosides, for example, in the highly successful anti-HIV and HBV drug tenofovir. In contrast, introduction of flexibility to the nucleobase scaffold has only more recently gained significance with the invention of our fleximers. The history, development, and some biological relevance for this innovative class of nucleosides are d

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7

Cabrita, Miguel A., Stephen A. Baldwin, James D. Young, and Carol E. Cass. "Molecular biology and regulation of nucleoside and nucleobase transporter proteins in eukaryotes and prokaryotes." Biochemistry and Cell Biology 80, no. 5 (2002): 623–38. http://dx.doi.org/10.1139/o02-153.

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The molecular cloning of cDNAs encoding nucleoside transporter proteins has greatly advanced understanding of how nucleoside permeants are translocated across cell membranes. The nucleoside transporter proteins identified thus far have been categorized into five distinct superfamilies. Two of these superfamilies, the equilibrative and concentrative nucleoside transporters, have human members and these will be examined in depth in this review. The human equilibrative nucleoside transporters translocate nucleosides and nucleobases bidirectionally down their concentration gradients and are import

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8

Erickson-Viitanen, Susan, Jing-Tao Wu, Guoen Shi, et al. "Cellular Pharmacology of D-d4FC, a Nucleoside Analogue Active against Drug-Resistant HIV." Antiviral Chemistry and Chemotherapy 14, no. 1 (2003): 39–47. http://dx.doi.org/10.1177/095632020301400104.

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The backbone of effective highly active antiretroviral therapy regimens for the treatment of HIV infections currently contains at least two nucleosides. Among the features that influence the potency of each component of a regimen and the overall efficacy of the combination are the cellular uptake and bioconversion of nucleoside analogues to their active triphosphate form, and the extent of possible interactions in these steps that might occur when more than one nucleoside is used in a regimen. D-d4FC (Reverset™), a new cytidine analogue with the ability to inhibit many nucleoside-resistant vir

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9

Komiotis, Dimitri, Stella Manta, Evangelia Tsoukala, and Niki Tzioumaki. "Antiviral Unsaturated Nucleosides." Anti-Infective Agents in Medicinal Chemistry 7, no. 4 (2008): 219–44. http://dx.doi.org/10.2174/187152108785908848.

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10

Lee, Kyeong, and Chung K. Chu. "Molecular Modeling Approach to Understanding the Mode of Action of l-Nucleosides as Antiviral Agents." Antimicrobial Agents and Chemotherapy 45, no. 1 (2001): 138–44. http://dx.doi.org/10.1128/aac.45.1.138-144.2001.

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ABSTRACT A series of unnatural l-nucleosides such as 3TC, FTC and l-FMAU have been found to be potent antiviral agents. The mode of action of l-nucleosides has been found to be similar to that of d-nucleosides as antiviral agents, despite their unnatural stereochemistry, that is, nucleotide formation by kinases followed by interaction with the reverse transcriptase (RT) of HIV or DNA polymerase. To date, the mode of action of nucleoside inhibitors at the molecular level with respect to the active conformations of the 5′-triphosphates as well as the interaction with the RT is not known. Recentl

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11

Podgorska, Marzena, Katarzyna Kocbuch, and Tadeusz Pawelczyk. "Recent advances in studies on biochemical and structural properties of equilibrative and concentrative nucleoside transporters." Acta Biochimica Polonica 52, no. 4 (2005): 749–58. http://dx.doi.org/10.18388/abp.2005_3386.

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Nucleoside transporters (NT) facilitate the movement of nucleosides and nucleobases across cell membranes. NT-mediated transport is vital for the synthesis of nucleic acids in cells that lack de novo purine synthesis. Some nucleosides display biological activity and act as signalling molecules. For example, adenosine exerts a potent action on many physiological processes including vasodilatation, hormone and neurotransmitter release, platelet aggregation, and lipolysis. Therefore, carrier-mediated transport of this nucleoside plays an important role in modulating cell function, because the eff

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12

van Roey, P., W. A. Pangborn, R. F. Schinazi, G. Painter, and D. C. Liotta. "Absolute Configuration of the Antiviral Agent (−)-cis-5-Fluoro-1-[2-Hydroxymethyl)-1,3-Oxathiolan-5-yl]Cytosine." Antiviral Chemistry and Chemotherapy 4, no. 6 (1993): 369–75. http://dx.doi.org/10.1177/095632029300400609.

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The structure and absolute configuration of (−)- cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine (FTC), has been determined by X-ray crystallographic analysis. The results confirm that the L-isomer of the nucleoside analogue is the most active enantiomer and that the correct absolute configuration of (−)-FTC is 5-fluoro-(2′R,5′S)-(−)-1-[2-hydroxymethyl)oxathiolan-5-yl]-fluorocytosine. The two molecules in the asymmetric unit show conformations that combine conformational features of two other classes of potent antiviral nucleosides. Both oxathiolane rings have the 3′-sulphur ato

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13

MANSOUR, T. S., and R. STORER. "ChemInform Abstract: Antiviral Nucleosides." ChemInform 28, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199748326.

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14

YOKOZEKI, KENZO, HYDEYUKI SHIRAE, and KOJI KUBOTA. "Enzymatic Production of Antiviral Nucleosides by the Application of Nucleoside Phosphorylase." Annals of the New York Academy of Sciences 613, no. 1 Enzyme Engine (1990): 757–59. http://dx.doi.org/10.1111/j.1749-6632.1990.tb18259.x.

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15

Hyun Oh, Chang, and Joon Hee Hong. "Synthesis and Antiviral Evaluation of Novel Cyclopropyl Nucleosides, Phosphonate Nucleosides and Phosphonic Acid Nucleosides." Archiv der Pharmazie 339, no. 9 (2006): 507–12. http://dx.doi.org/10.1002/ardp.200600031.

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16

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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17

Shanmugasundaram, Muthian, Annamalai Senthilvelan, and Anilkumar R. Kore. "C-5 Substituted Pyrimidine Nucleotides/Nucleosides: Recent Progress in Synthesis, Functionalization, and Applications." Current Organic Chemistry 23, no. 13 (2019): 1439–68. http://dx.doi.org/10.2174/1385272823666190809124310.

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The chemistry of C5 substituted pyrimidine nucleotide serves as a versatile molecular biology probe for the incorporation of DNA/RNA that has been involved in various molecular biology applications such as gene expression, chromosome, and mRNA fluorescence in situ hybridization (FISH) experiment, mutation detection on arrays and microarrays, in situ RT-PCR, and PCR. In addition to C5 substituted pyrimidine nucleotide, C5 substituted pyrimidine nucleoside displays a broad spectrum of biological applications such as antibacterial, antiviral and anticancer activities. This review focusses on the

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18

Izawa, Kunisuke, and H. Shiragami. "Practical syntheses of antiviral nucleosides." Pure and Applied Chemistry 70, no. 2 (1998): 313–18. http://dx.doi.org/10.1351/pac199870020313.

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19

Freeman, Sally, and John M. Gardiner. "Acyclic nucleosides as antiviral compounds." Molecular Biotechnology 5, no. 2 (1996): 125–37. http://dx.doi.org/10.1007/bf02789061.

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20

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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21

Govindarajan, Rajgopal, George P. H. Leung, Mingyan Zhou, Chung-Ming Tse, Joanne Wang, and Jashvant D. Unadkat. "Facilitated mitochondrial import of antiviral and anticancer nucleoside drugs by human equilibrative nucleoside transporter-3." American Journal of Physiology-Gastrointestinal and Liver Physiology 296, no. 4 (2009): G910—G922. http://dx.doi.org/10.1152/ajpgi.90672.2008.

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human equilibrative nucleoside transporter-3 (hENT3) was recently reported as a pH-dependent, intracellular (lysosomal) transporter capable of transporting anti-human immunodeficiency virus (HIV) dideoxynucleosides (ddNs). Because most anti-HIV ddNs (e.g., zidovudine, AZT) exhibit clinical mitochondrial toxicity, we investigated whether hENT3 facilitates transport of anti-HIV ddNs into the mitochondria. Cellular fractionation and immunofluorescence microscopy studies in several human cell lines identified a substantial presence of hENT3 in the mitochondria, with additional presence at the cell

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22

Jansa, Petr, Viktor Kolman, Alexandra Kostinová, Martin Dračínský, Helena Mertlíková-Kaiserová, and Zlatko Janeba. "Efficient synthesis and biological properties of the 2′-trifluoromethyl analogues of acyclic nucleosides and acyclic nucleoside phosphonates." Collection of Czechoslovak Chemical Communications 76, no. 10 (2011): 1187–98. http://dx.doi.org/10.1135/cccc2011105.

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Efficient and optimized procedure for the preparation of several acyclic nucleosides and acyclic nucleoside phosphonates substituted at the C-2′ position of the aliphatic part by the trifluoromethyl group is described. Trifluoromethyloxirane was found to be an excellent reagent for the introduction of the 1,1,1-trifluoropropan-2-ol moiety. Surprisingly, the next reaction of these 1,1,1-trifluoropropan-2-ols with the reagent for the introduction of the methylphosphonic residue afforded the desired phosphonates in very high yields and finally a novel simple and scalable procedure for the isolati

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23

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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24

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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25

Schinazi, Raymond F., Grigorii G. Sivets, Mervi A. Detorio, et al. "Synthesis and antiviral evaluation of 2′,3′-dideoxy-2′,3′-difluoro-D-arabinofuranosyl 2,6-disubstituted purine nucleosides." Heterocyclic Communications 21, no. 5 (2015): 315–27. http://dx.doi.org/10.1515/hc-2015-0174.

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AbstractThe synthesis of new 2,6-disubstituted purine 2′,3′-dideoxy-2′,3′-difluoro-D-arabino nucleosides is reported. Their ability to block HIV and HCV replication along with their cytotoxicity toward Huh-7 cells, human lymphocyte, CEM and Vero cells was also assessed. Among them, β-2,6-diaminopurine nucleoside 25 and guanosine derivative 27 demonstrate potent anti-HIV-1 activity (EC50 = 0.56 and 0.65 μm; EC90 = 4.2 and 3.1 μm) while displaying only moderate cytotoxicity in primary human lymphocytes.

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26

Rossi, L., S. Serafini, P. Franchetti, et al. "Targeting Nucleotide Dimers Containing Antiviral Nucleosides." Current Medicinal Chemistry -Anti-Infective Agents 4, no. 1 (2005): 37–54. http://dx.doi.org/10.2174/1568012052931214.

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27

Agrofoglio, Luigi, and Steven Nolan. "Olefin Metathesis Route to Antiviral Nucleosides." Current Topics in Medicinal Chemistry 5, no. 15 (2005): 1541–58. http://dx.doi.org/10.2174/156802605775009739.

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28

Loakes, D., D. M. Brown, N. Mahmood, J. Balzarini, and E. De Clercq. "Antiviral Activity of Bicyclic Pyrimidine Nucleosides." Antiviral Chemistry and Chemotherapy 6, no. 6 (1995): 371–78. http://dx.doi.org/10.1177/095632029500600604.

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A number of pyrimidine nucleosides, which may show two hydrogen bonding modes, have been prepared and tested for antiviral activity against a series of viruses. Whilst none of the compounds described showed significant activity against human immunodeficiency virus (HIV), the bicyclic 2′-deoxynucleoside, [2], derived from the base 6H,8H-3,4-dihydropyrimido[4,5-c][1,2]oxazin-7-one, was shown to inhibit herpes simplex virus type 1 (HSV-1) at similar concentrations as BVDU1 and ACV. Compounds 13, 6-(2-deoxyribofuranosyl)-6H,8H-2-methyl-3,4-dihydropyrimido[4,5-c][1,2]oxazin-7-one, and 14, N4-hydrox

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29

Cluet, F., A. Haudrechy, P. Le Ber, P. Sinaÿ, and A. Wick. "Synthesis of potentially antiviral cyclopropyl nucleosides." Synlett 1994, no. 11 (1994): 913–15. http://dx.doi.org/10.1055/s-1994-23046.

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30

Shipitsyn, Alexander V., Natalya F. Zakirova, Evgeny F. Belanov, et al. "Phosphorodiamides as Prodrugs for Antiviral Nucleosides." Nucleosides, Nucleotides and Nucleic Acids 22, no. 5-8 (2003): 963–66. http://dx.doi.org/10.1081/ncn-120022696.

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31

Lee, Yoon-Suk, and Byeang Hyean Kim. "Heterocyclic nucleoside analogues: design and synthesis of antiviral, modified nucleosides containing isoxazole heterocycles." Bioorganic & Medicinal Chemistry Letters 12, no. 10 (2002): 1395–97. http://dx.doi.org/10.1016/s0960-894x(02)00182-8.

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32

YOKOZEKI, K., H. SHIRAE, and K. KUBOTA. "ChemInform Abstract: Enzymatic Production of Antiviral Nucleosides by the Application of Nucleoside Phosphorylase." ChemInform 22, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199136092.

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33

Meier, Chris. "Nucleoside diphosphate and triphosphate prodrugs – An unsolvable task?" Antiviral Chemistry and Chemotherapy 25, no. 3 (2017): 69–82. http://dx.doi.org/10.1177/2040206617738656.

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In this review, our recent advances in the development of nucleoside di- and nucleoside triphosphate prodrugs is summarized. Previously, we had developed a successful membrane-permeable pronucleotide system for the intracellular delivery of nucleoside monophosphates as well, the so-called cycloSal-approach. In contrast to that work in which the delivery is initiated by a chemically driven hydrolysis reaction, for the di- and triphosphate delivery, an enzymatic trigger mechanism involving (carboxy)esterases had to be used. The other features of the new pronucleotide approaches are: (i) lipophil

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34

Kim, Aihong, and Joon Hee Hong. "Synthesis and Antiviral Evaluation of Novel Exomethylene Acyclic Nucleosides and Phosphonic Acid Nucleosides." Archiv der Pharmazie 338, no. 11 (2005): 528–33. http://dx.doi.org/10.1002/ardp.200500187.

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35

Coen, Natacha, Sophie Duraffour, Dimitri Topalis, Robert Snoeck, and Graciela Andrei. "Spectrum of Activity and Mechanisms of Resistance of Various Nucleoside Derivatives against Gammaherpesviruses." Antimicrobial Agents and Chemotherapy 58, no. 12 (2014): 7312–23. http://dx.doi.org/10.1128/aac.03957-14.

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ABSTRACTThe susceptibilities of gammaherpesviruses, including Epstein-Barr virus (EBV), Kaposi's sarcoma-associated herpesvirus (KSHV), and animal rhadinoviruses, to various nucleoside analogs was investigated in this work. Besides examining the antiviral activities and modes of action of antivirals currently marketed for the treatment of alpha- and/or betaherpesvirus infections (including acyclovir, ganciclovir, penciclovir, foscarnet, and brivudin), we also investigated the structure-activity relationship of various 5-substituted uridine and cytidine molecules. The antiviral efficacy of nucl

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36

Shigeta, S., S. Mori, F. Watanabe, et al. "Synthesis and Antiherpesvirus Activities of 5-Alkyl-2-Thiopyrimidine Nucleoside Analogues." Antiviral Chemistry and Chemotherapy 13, no. 2 (2002): 67–82. http://dx.doi.org/10.1177/095632020201300201.

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Twenty 5-alkyl-2-thiopyrimidine nucleosides were newly synthesized and examined for antiviral activities against herpes simplex virus (HSV), varicella-zoster virus (VZV) and human cytomegalovirus (HCMV). In this study, 2′-deoxy-5- alkyl-2-thiocytidine analogues had lower 50% effective concentration (EC50) values against HSV- 1, and 2/-deoxy-5-alkyl-2-thiouridine analogues showed lower EC50 against VZV than their congeners of arabinoside form. Among the compounds examined, 2′-deoxy-5-ethyl and 5-propyl- 2-thiocytidine (TN-53 and TN-54) were most potent and selective anti-HSV compounds. Their EC

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37

Serra, I., D. Ubiali, A. M. Albertini, G. Amati, S. Daly, and M. Terreni. "Microbial nucleoside phosphorylases as efficient biocatalysts for the synthesis of antiviral and antitumoral nucleosides." Journal of Biotechnology 150 (November 2010): 408. http://dx.doi.org/10.1016/j.jbiotec.2010.09.545.

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38

Gumina, Giuseppe, Youhoon Chong, Hyunah Choo, Gyu-Yong Song, and Chung Chu. "L - Nucleosides: Antiviral Activity and Molecular Mechanism." Current Topics in Medicinal Chemistry 2, no. 10 (2002): 1065–86. http://dx.doi.org/10.2174/1568026023393138.

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39

Meng, Wei-Dong, and Feng-Ling Qing. "Fluorinated Nucleosides as Antiviral and Antitumor Agents." Current Topics in Medicinal Chemistry 6, no. 14 (2006): 1499–528. http://dx.doi.org/10.2174/156802606777951082.

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40

Siddiqui, M. Arshad, William L. Brown, Nghe Nguyen-Ba, et al. "Antiviral optically pure dioxolane purine nucleosides analogues." Bioorganic & Medicinal Chemistry Letters 3, no. 8 (1993): 1543–46. http://dx.doi.org/10.1016/s0960-894x(00)80014-1.

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41

Herdewijn, Piet. "Structural requirements for antiviral activity in nucleosides." Drug Discovery Today 2, no. 6 (1997): 235–42. http://dx.doi.org/10.1016/s1359-6446(97)01047-7.

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42

Chu, Chung K., Li Ma, Sureyya Olgen, et al. "Synthesis and Antiviral Activity of Oxaselenolane Nucleosides." Journal of Medicinal Chemistry 43, no. 21 (2000): 3906–12. http://dx.doi.org/10.1021/jm990113x.

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43

Nair, Vasu, and Michael A. Ussery. "New hypoxanthine nucleosides with RNA antiviral activity." Antiviral Research 19, no. 2 (1992): 173–78. http://dx.doi.org/10.1016/0166-3542(92)90076-h.

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44

Pathy, Dr Krishnasarma. "Antiviral Nucleosides-Flu Viruses-Quinolines-COVID-19." International Journal of Research Studies in Medical and Health Sciences 5, no. 8 (2020): 14–25. http://dx.doi.org/10.22259/ijrsmhs.0508002.

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45

Carangio, A., S. Srinivasan, C. McGuigan, et al. "Bicyclic Nucleoside Inhibitors of Varicella-Zoster Virus: Effect of Terminal Aryl Substitution in the Side-Chain." Antiviral Chemistry and Chemotherapy 13, no. 5 (2002): 263–71. http://dx.doi.org/10.1177/095632020201300501.

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We have previously reported the discovery and preliminary structure-activity relationships of a new class of inhibitors of varicella-zoster virus (VZV). These novel furanopyrimidine nucleosides bear unusual bicyclic base moieties and exhibit complete specificity for VZV. Limited in vitro cytotoxicity has been detected and the bicyclic nucleosides are now well established as a new family of potent antivirals. Our initial studies revealed an absolute requirement of a long alkyl side-chain, with an optimal chain length of C8-C10, for antiviral activity. Following further studies, we recently repo

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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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Tamborini, Lucia, Clelia Previtali, Francesca Annunziata, et al. "An Enzymatic Flow-Based Preparative Route to Vidarabine." Molecules 25, no. 5 (2020): 1223. http://dx.doi.org/10.3390/molecules25051223.

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The bi-enzymatic synthesis of the antiviral drug vidarabine (arabinosyladenine, ara-A), catalyzed by uridine phosphorylase from Clostridium perfringens (CpUP) and a purine nucleoside phosphorylase from Aeromonas hydrophila (AhPNP), was re-designed under continuous-flow conditions. Glyoxyl–agarose and EziGTM1 (Opal) were used as immobilization carriers for carrying out this preparative biotransformation. Upon setting-up reaction parameters (substrate concentration and molar ratio, temperature, pressure, residence time), 1 g of vidarabine was obtained in 55% isolated yield and >99% purity by

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Cobb, Alexander J. A., Antonio Dell’Isola, Ban O. Abdulsattar, et al. "Synthesis and antiviral activity of novel spirocyclic nucleosides." New Journal of Chemistry 42, no. 22 (2018): 18363–80. http://dx.doi.org/10.1039/c8nj02777c.

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Papadakis, Georgios, Maria Gerasi, Robert Snoeck, et al. "Synthesis of New Imidazopyridine Nucleoside Derivatives Designed as Maribavir Analogues." Molecules 25, no. 19 (2020): 4531. http://dx.doi.org/10.3390/molecules25194531.

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The strong inhibition of Human Cytomegalovirus (HCMV) replication by benzimidazole nucleosides, like Triciribine and Maribavir, has prompted us to expand the structure–activity relationships of the benzimidazole series, using as a central core the imidazo[4,5-b]pyridine scaffold. We have thus synthesized a number of novel amino substituted imidazopyridine nucleoside derivatives, which can be considered as 4-(or 7)-aza-d-isosters of Maribavir and have evaluated their potential antiviral activity. The target compounds were synthesized upon glycosylation of suitably substituted 2-aminoimidazopyri

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Graci, Jason D., Kathleen Too, Eric D. Smidansky, et al. "Lethal Mutagenesis of Picornaviruses with N-6-Modified Purine Nucleoside Analogues." Antimicrobial Agents and Chemotherapy 52, no. 3 (2008): 971–79. http://dx.doi.org/10.1128/aac.01056-07.

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ABSTRACT RNA viruses exhibit extraordinarily high mutation rates during genome replication. Nonnatural ribonucleosides that can increase the mutation rate of RNA viruses by acting as ambiguous substrates during replication have been explored as antiviral agents acting through lethal mutagenesis. We have synthesized novel N-6-substituted purine analogues with ambiguous incorporation characteristics due to tautomerization of the nucleobase. The most potent of these analogues reduced the titer of poliovirus (PV) and coxsackievirus (CVB3) over 1,000-fold during a single passage in HeLa cell cultur

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