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Journal articles on the topic 'Synthesis of nucleotide analogues'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 February 2022

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1

Dutartre, Hélène, Cécile Bussetta, Joëlle Boretto, and Bruno Canard. "General Catalytic Deficiency of Hepatitis C Virus RNA Polymerase with an S282T Mutation and Mutually Exclusive Resistance towards 2′-Modified Nucleotide Analogues." Antimicrobial Agents and Chemotherapy 50, no. 12 (September 25, 2006): 4161–69. http://dx.doi.org/10.1128/aac.00433-06.

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ABSTRACT The hepatitis C virus (HCV) RNA-dependent RNA polymerase NS5B is an important target for antiviral therapies. NS5B is able to initiate viral RNA synthesis de novo and then switch to a fast and processive RNA elongation synthesis mode. The nucleotide analogue 2′-C-methyl CTP (2′-C-Me-CTP) is the active metabolite of NM283, a drug currently in clinical phase II trials. The resistance mutation S282T can be selected in HCV replicon studies. Likewise, 2′-O-Me nucleotides are active both against the purified polymerase and in replicon studies. We have determined the molecular mechanism by which the S282T mutation confers resistance to 2′-modified nucleotide analogues. 2′-C-Me-CTP is no longer incorporated during the initiation step of RNA synthesis and is discriminated 21-fold during RNA elongation by the NS5B S282T mutant. Strikingly, 2′-O-methyl CTP sensitivity does not change during initiation, but the analogue is no longer incorporated during elongation. This mutually exclusive resistance mechanism suggests not only that “2′-conformer” analogues target distinct steps in RNA synthesis but also that these analogues have interesting potential in combination therapies. In addition, the presence of the S282T mutation induces a general cost in terms of polymerase efficiency that may translate to decreased viral fitness: natural nucleotides become 5- to 20-fold less efficiently incorporated into RNA by the NS5B S282T mutant. As in the case for human immunodeficiency virus, our results might provide a mechanistic basis for the rational combination of drugs for low-fitness viruses.

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2

Nairne, R. James D., Lea Pickering, and Clifford L. Smith. "Synthesis of pyrrole carboxamide nucleotide triphosphates—putative labelled nucleotide analogues." Tetrahedron Letters 43, no. 12 (March 2002): 2289–91. http://dx.doi.org/10.1016/s0040-4039(02)00225-3.

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3

Chamberlain, Brian T., Thomas G. Upton, Boris A. Kashemirov, and Charles E. McKenna. "α-Azido Bisphosphonates: Synthesis and Nucleotide Analogues." Journal of Organic Chemistry 76, no. 12 (June 17, 2011): 5132–36. http://dx.doi.org/10.1021/jo200045a.

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4

Bordoni, Cinzia, Cecilia Maria Cima, Elisa Azzali, Gabriele Costantino, and Andrea Brancale. "Microwave-assisted organic synthesis of nucleoside ProTide analogues." RSC Advances 9, no. 35 (2019): 20113–17. http://dx.doi.org/10.1039/c9ra01754b.

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5

Scism, Robert A., Donald F. Stec, and Brian O. Bachmann. "Synthesis of Nucleotide Analogues by a Promiscuous Phosphoribosyltransferase." Organic Letters 9, no. 21 (October 2007): 4179–82. http://dx.doi.org/10.1021/ol7016802.

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6

Xu, Yunjian, Frank Schwede, Hans Wienk, Anders Tengholm, and Holger Rehmann. "A Membrane Permeable Prodrug of S223 for Selective Epac2 Activation in Living Cells." Cells 8, no. 12 (December 6, 2019): 1589. http://dx.doi.org/10.3390/cells8121589.

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Signalling by cyclic adenosine monophosphate (cAMP) occurs via various effector proteins, notably protein kinase A and the guanine nucleotide exchange factors Epac1 and Epac2. These proteins are activated by cAMP binding to conserved cyclic nucleotide binding domains. The specific roles of the effector proteins in various processes in different types of cells are still not well defined, but investigations have been facilitated by the development of cyclic nucleotide analogues with distinct selectivity profiles towards a single effector protein. A remaining challenge in the development of such analogues is the poor membrane permeability of nucleotides, which limits their applicability in intact living cells. Here, we report the synthesis and characterisation of S223-AM, a cAMP analogue designed as an acetoxymethyl ester prodrug to overcome limitations of permeability. Using total internal reflection imaging with various fluorescent reporters, we show that S223-AM selectively activates Epac2, but not Epac1 or protein kinase A, in intact insulin-secreting β-cells, and that this effect was associated with pronounced activation of the small G-protein Rap. A comparison of the effects of different cAMP analogues in pancreatic islet cells deficient in Epac1 and Epac2 demonstrates that cAMP-dependent Rap activity at the β-cell plasma membrane is exclusively dependent on Epac2. With its excellent selectivity and permeability properties, S223-AM should get broad utility in investigations of cAMP effector involvement in many different types of cells.

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7

Laux, Wolfgang HG, Stéphane Priet, Karine Alvarez, Suzanne Peyrottes, and Christian Périgaud. "Synthesis and substrate properties towards HIV-1 reverse transcriptase of new diphosphate analogues of 9-[(2-phosphonomethoxy)ethyl]adenine." Antiviral Chemistry and Chemotherapy 26 (January 2018): 204020661875763. http://dx.doi.org/10.1177/2040206618757636.

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Background The replacement of β,γ-pyrophosphate by β,γ-phosphonate moieties within the triphosphate chain of 5′-triphosphate nucleoside analogues was previously studied for various antiviral nucleoside analogues such as AZT and 2′,3′-dideoxynucleosides. Thus, it has been shown that these chemical modifications could preserve, in some cases, the terminating substrate properties of the triphosphate analogue for HIV-RT. Herein, we aimed to study such 5′-triphosphate mimics based on the scaffold of the well-known antiviral agent 9-[(2-phosphonomethoxy)ethyl]adenine (PMEA, Adefovir). Methods Synthesis involved coupling of a morpholidate derivative of PMEA with appropriate pyrophosphoryl analogues. The relative efficiencies of incorporation of the studied diphosphate phosphonates were measured using subtype B WT HIV-1 RT in an in vitro susceptibility assay, in comparison to the parent nucleotide analogue (PMEApp). Results Searching for nucleoside 5′-triphosphate mimics, we have synthesized and studied a series of diphosphate analogues of PMEA bearing non hydrolysable bonds between the and phosphorus atoms. We also examined their relative inhibitory capacity towards HIV-1 reverse transcriptase in comparison to the parent nucleotide analogue (PMEApp). Only one of them appeared as a weak inhibitor (IC50 = 403.0 ± 75.5 µM) and proved to be less effective than PMEApp (IC50 = 6.4 ± 0.8 µM). Conclusion PMEA diphosphoryl derivatives were designed as potential substrates and/or inhibitors of various viral polymerases. These modifications dramatically affect their ability to inhibit HIV-RT.

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8

Zhou, Ding, Irene M. Lagoja, Arthur Van Aerschot, and Piet Herdewijn. "Synthesis of Aminopropyl Phosphonate Nucleosides with Purine and Pyrimidine Bases." Collection of Czechoslovak Chemical Communications 71, no. 1 (2006): 15–34. http://dx.doi.org/10.1135/cccc20060015.

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The synthesis and antiviral evaluation of new acyclic phosphonate nucleosides related to HPMPC (Cidofovir) has been described. These aminopropyl phosphonate nucleosides 1-3 have an amino function within either the acyclic chain (series 2 and 3) or as substituent (series 1). Both purine and pyrimidine nucleotide analogues have been synthesized. In contrast to HPMPC the oxygen analogue of 2c, only a weak antiherpes virus activity could be demonstrated for 2b and 2c.

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9

Alexander, Petr, V. V. Krishnamurthy, and Ernest J. Prisbe. "Synthesis and Antiviral Activity of Pyranosylphosphonic Acid Nucleotide Analogues." Journal of Medicinal Chemistry 39, no. 6 (January 1996): 1321–30. http://dx.doi.org/10.1021/jm950788+.

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10

GI, H. J., Y. XIANG, R. F. SCHINAZI, and K. ZHAO. "ChemInform Abstract: Synthesis of Dihydroisoxazole Nucleoside and Nucleotide Analogues." ChemInform 28, no. 21 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199721232.

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11

Fateev, Ilja V., Ekaterina V. Sinitsina, Aiguzel U. Bikanasova, Maria A. Kostromina, Elena S. Tuzova, Larisa V. Esipova, Tatiana I. Muravyova, Alexei L. Kayushin, Irina D. Konstantinova, and Roman S. Esipov. "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 substrates were determined. Two nucleotides were synthesized: 9-(β-D-ribofuranosyl)-2-chloroadenine 5'-monophosphate (2-Сl-AMP) using TthAPRT and 1-(β-D-ribofuranosyl)pyrazolo[3,4-d]pyrimidine-4-one 5'-monophosphate (Allop-MP) using TthНPRT.

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12

Wolters, Justina C., Gerard Roelfes, and Bert Poolman. "Design and Synthesis of ATP-Based Nucleotide Analogues and Profiling of Nucleotide-Binding Proteins." Bioconjugate Chemistry 22, no. 7 (July 20, 2011): 1345–53. http://dx.doi.org/10.1021/bc100592q.

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13

Rejman, Dominik, Radek Pohl, Petr Kočalka, Milena Masojídková, and Ivan Rosenberg. "Pyrrolidine N-alkylphosphonates and related nucleotide analogues: synthesis and stereochemistry." Tetrahedron 65, no. 18 (May 2009): 3673–81. http://dx.doi.org/10.1016/j.tet.2009.02.071.

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14

Alexander, Petr, Antonín Holý, Miloš Buděšínský, and Milena Masojídková. "Synthesis of Acyclic Nucleotide Analogues Derived from N3-Substituted Isoguanine." Collection of Czechoslovak Chemical Communications 65, no. 11 (2000): 1713–25. http://dx.doi.org/10.1135/cccc20001713.

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Reaction of 9-benzyl-6-{[(dimethylamino)methylidene]amino}purin-2(3H)-one (7) with ethylene carbonate gave a mixture of 9-benzyl-2-(2-hydroxyethoxy)purin-6-amine (10) and 2-amino-9-benzyl-3-(2-hydroxyethyl)purin-2(3H)-one (11). This mixture reacted with diisopropyl (tosyloxymethyl)phosphonate in the presence of NaH followed by catalytic hydrogenation and bromotrimethylsilane treatment to afford isomeric 6-amino-3-[2-(phosphonomethoxy)ethyl]purin-2(3H)-one (3) and 2-[2-(phosphonomethoxy)ethoxy]purin- 6-amine (15). Similar treatment of compound7with tritylglycidol gave two isomeric 2-hydroxy-3-(trityloxy)propyl derivatives18,20which were subsequently condensed with diisopropyl (tosyloxymethyl)phosphonate to afford protected diester intermediates21and22; these compounds were transformed by hydrogenolysis and ester cleavage with bromotrimethylsilane to the isomeric 6-amino-3-[3-hydroxy-2-(phosphonomethoxy)propyl]- purin-2(3H)-one (2) and 2-[3-hydroxy-2-(phosphonomethoxy)propoxy]purin-6-amine (24). None of the free phosphonates2,3,15or24exhibited any antiviral or cytostatic activity.

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15

Jordan, Bertrand. "Extension du domaine du codage : l’ADN hachimoji." médecine/sciences 35, no. 5 (May 2019): 483–85. http://dx.doi.org/10.1051/medsci/2019080.

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The synthesis of four new nucleotide analogues that can form hydrogen bonds within the DNA double helix and can be incorporated without distortion of the structure extends the possibilities of synthetic biology. Although functional use of these analogues remains in the future, they already have interesting applications and represent an important step forward.

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16

Holý, A., M. Hocek, J. Balzarini, and E. De Clercq. "Synthesis of acyclic nucleotide analogues derived from 2-(aminomethyl)purine bases." Antiviral Research 26, no. 3 (March 1995): A305. http://dx.doi.org/10.1016/0166-3542(95)94845-s.

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17

Hellendahl, Katja F., Sarah Kamel, Albane Wetterwald, Peter Neubauer, and Anke Wagner. "Human Deoxycytidine Kinase Is a Valuable Biocatalyst for the Synthesis of Nucleotide Analogues." Catalysts 9, no. 12 (November 27, 2019): 997. http://dx.doi.org/10.3390/catal9120997.

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Natural ribonucleoside-5’-monophosphates are building blocks for nucleic acids which are used for a number of purposes, including food additives. Their analogues, additionally, are used in pharmaceutical applications. Fludarabine-5´-monophosphate, for example, is effective in treating hematological malignancies. To date, ribonucleoside-5’-monophosphates are mainly produced by chemical synthesis, but the inherent drawbacks of this approach have led to the development of enzymatic synthesis routes. In this study, we evaluated the potential of human deoxycytidine kinase (HsdCK) as suitable biocatalyst for the synthesis of natural and modified ribonucleoside-5’-monophosphates from their corresponding nucleosides. Human dCK was heterologously expressed in E. coli and immobilized onto Nickel-nitrilotriacetic acid (Ni-NTA) superflow. A screening of the substrate spectrum of soluble and immobilized biocatalyst revealed that HsdCK accepts a wide range of natural and modified nucleosides, except for thymidine and uridine derivatives. Upon optimization of the reaction conditions, HsdCK was used for the synthesis of fludarabine-5´-monophosphate using increasing substrate concentrations. While the soluble biocatalyst revealed highest product formation with the lowest substrate concentration of 0.3 mM, the product yield increased with increasing substrate concentrations in the presence of the immobilized HsdCK. Hence, the application of immobilized HsdCK is advantageous upon using high substrate concentration which is relevant in industrial applications.

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18

Nguyen Van, Tai, Audrey Hospital, Corinne Lionne, Lars P. Jordheim, Charles Dumontet, Christian Périgaud, Laurent Chaloin, and Suzanne Peyrottes. "Beta-hydroxyphosphonate ribonucleoside analogues derived from 4-substituted-1,2,3-triazoles as IMP/GMP mimics: synthesis and biological evaluation." Beilstein Journal of Organic Chemistry 12 (July 18, 2016): 1476–86. http://dx.doi.org/10.3762/bjoc.12.144.

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A series of seventeen β-hydroxyphosphonate ribonucleoside analogues containing 4-substituted-1,2,3-triazoles was synthesized and fully characterized. Such compounds were designed as potential inhibitors of the cytosolic 5’-nucleotidase II (cN-II), an enzyme involved in the regulation of purine nucleotide pools. NMR and molecular modelling studies showed that a few derivatives adopted similar structural features to IMP or GMP. Five derivatives were identified as modest inhibitors with 53 to 64% of cN-II inhibition at 1 mM.

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19

Johansson, Tommy, and Jacek Stawinski. "Synthesis of Nucleotide Analogues with Pyridylphosphonate and Pyridylphosphono thio ate Internucleotide Linkages." Phosphorus, Sulfur, and Silicon and the Related Elements 177, no. 6-7 (June 1, 2002): 1779–82. http://dx.doi.org/10.1080/10426500212320.

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20

Moore, Chad L., Molly Chiaramonte, Tamara Higgins, and Robert D. Kuchta. "Synthesis of Nucleotide Analogues That Potently and Selectively Inhibit Human DNA Primase†." Biochemistry 41, no. 47 (November 2002): 14066–75. http://dx.doi.org/10.1021/bi026468r.

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21

Guo, Jia, Lin Yu, Nicholas J. Turro, and Jingyue Ju. "An Integrated System for DNA Sequencing by Synthesis Using Novel Nucleotide Analogues." Accounts of Chemical Research 43, no. 4 (April 20, 2010): 551–63. http://dx.doi.org/10.1021/ar900255c.

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22

Alexander, Petr, Antonin Holy, Milos Budesinsky, and Milena Masojidkova. "ChemInform Abstract: Synthesis of Acyclic Nucleotide Analogues Derived from N3-Substituted Isoguanine." ChemInform 32, no. 20 (May 15, 2001): no. http://dx.doi.org/10.1002/chin.200120196.

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23

MARQUEZ, V. E. "ChemInform Abstract: Design, Synthesis, and Antiviral Activity of Nucleoside and Nucleotide Analogues." ChemInform 22, no. 17 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199117310.

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24

Brel, V. K. "Synthesis and some transformation of acyclic nucleotide phosphonate analogues with triple bond." Nucleic Acids Symposium Series 52, no. 1 (September 1, 2008): 535–36. http://dx.doi.org/10.1093/nass/nrn271.

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25

Pankiewicz, Krzysztof W., Krystyna B. Lesiak, and Kyoichi A. Watanabe. "Synthesis of Methylenebis(Phosphonate) Analogues of Nucleotide Coenzymes. A Novel Coupling Mechanism." Phosphorus, Sulfur, and Silicon and the Related Elements 144, no. 1 (January 1, 1999): 671–74. http://dx.doi.org/10.1080/10426509908546334.

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26

Meldgaard, Michael, Nanna K. Nielsen, Murray Bremner, Ole S. Pedersen, Carl Erik Olsen, and Jesper Wengel. "Automated synthesis of branched oligodeoxynucleotide analogues using arabino-uridine as branching nucleotide." Journal of the Chemical Society, Perkin Transactions 1, no. 13 (1997): 1951–56. http://dx.doi.org/10.1039/a701228d.

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27

Janeba, Zlatko, Antonín Holý, Robert Snoeck, Graciela Andrei, Eric De Clercq, and Jan Balzarini. "Synthesis and Biological Evaluation of Acyclic Nucleotide Analogues of Bicyclic Pyrimidine Bases." Antiviral Research 82, no. 2 (May 2009): A58—A59. http://dx.doi.org/10.1016/j.antiviral.2009.02.139.

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28

Hocek, Michal, and Antonín Holý. "Perfluoroalkylation of 6-Iodopurines by Trimethyl(perfluoroalkyl)silanes. Synthesis of 6-(Perfluoroalkyl)purine Bases, Nucleosides and Acyclic Nucleotide Analogues." Collection of Czechoslovak Chemical Communications 64, no. 2 (1999): 229–41. http://dx.doi.org/10.1135/cccc19990229.

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A CuI/KF mediated perfluoroalkylation reaction of various 9-substituted 6-iodopurines 1 with trimethyl(trifluoromethyl)silane or heptafluoropropyl(trimethyl)silane was used for the synthesis of the corresponding 6-(trifluoromethyl)- and 6-(heptafluoropropyl)purine derivatives (purine bases, nucleosides and acyclic nucleotide analogues) in moderate to good yields.

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29

Agarwal, Sunita K., David J. Schultz, and Dennis A. Schaff. "APRT SELECTION SYSTEM IN PLANTS." HortScience 27, no. 11 (November 1992): 1160f—1160. http://dx.doi.org/10.21273/hortsci.27.11.1160f.

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Most cells have an active turnover of many of their nucleic acids (particularly some types of RNA) which through degradative processes result in the release of adenine, guanine and hypoxanthine. These free purines are converted to their corresponding nucleotides through salvage pathways. Adenine is converted to its nucleotide form AMP by Adenine phosphoribosyltransferase (APRT) which is one of the enzymes associated with the purine salvage pathway. Since all organisms have a de novo pathway for the formation of AMP, APRT is classified as a `salvage enzyme'. The APRT enzyme, in general, does not show a high degree of specificity for the exact structure of adenine and can also act on cytokinins and adenine derivatives like 2,6-diaminopurine, 2-fluoroadenine and 6-methylpurine. The APRT enzyme can utilize adenine analogues as substrate and convert them into their nucleotide forms which are toxic. Plants that lack APRT activity (APRT-plants) survive in the presense of these analogues. The amount of adenine analogue used for selecting APRT-plants is such that it kills all APRT+ (wild type) plants. APRT+ plants survive when grown in the presense of azaserine and alanosine that block de novo synthesis of AMP. APRT-plants transformed with the wild type cloned gene can be selected from a mixture of transformed and non-transformed plants by selecting in the presense of adenine, azaserine and alanosine. The presense of APRT activity can be confirmed by assaying for the APRT enzyme. APRT activity has been detected in many plant species. The presense of a positive forward and backward selection system can thus allow the use of APRT as a selectable marker in plant gene transfer systems.

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30

Janeba, Zlatko, Antonín Holý, Radek Pohl, Robert Snoeck, Graciela Andrei, Erik De Clercq, and Jan Balzarini. "Synthesis and biological evaluation of acyclic nucleotide analogues with a furo[2,3-d]pyrimidin-2(3H)-one base." Canadian Journal of Chemistry 88, no. 7 (July 2010): 628–38. http://dx.doi.org/10.1139/v10-054.

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As a part of a broader structure–activity relationship (SAR) study of bicyclic nucleoside analogues (BCNAs) [anti-varicella-zoster virus (anti-VZV) and anti-human cytomegalovirus (anti-HCMV) agents], a novel series of 2-(phosphonomethoxy)ethyl (PME) substituted furo[2,3-d]pyrimidin-2(3H)-ones was synthesized. The target acyclic nucleotide analogues were prepared by Sonogashira coupling of protected 5-iodo-1-[2-(phosphonomethoxy)ethyl]uracil with various 1-alkynes, followed by in situ Cu(I)-promoted intramolecular cyclization and standard removal of the isopropyl ester groups. None of the prepared PME analogues were active at subtoxic concentrations against VZV thymidine kinase competent (TK+), VZV thymidine kinase deficient (TK–), HCMV, or any other viruses tested.

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31

Baranowski, Marek R., Anna Nowicka, Anna M. Rydzik, Marcin Warminski, Renata Kasprzyk, Blazej A. Wojtczak, Jacek Wojcik, Timothy D. W. Claridge, Joanna Kowalska, and Jacek Jemielity. "Synthesis of Fluorophosphate Nucleotide Analogues and Their Characterization as Tools for19F NMR Studies." Journal of Organic Chemistry 80, no. 8 (April 8, 2015): 3982–97. http://dx.doi.org/10.1021/acs.joc.5b00337.

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32

HOLY, A., H. DVORAKOVA, J. JINDRICH, M. MASOJIDKOVA, M. BUDESINSKY, J. BALZARINI, G. ANDREI, and E. DE CLERCQ. "ChemInform Abstract: Acyclic Nucleotide Analogues Derived from 8-Azapurines: Synthesis and Antiviral Activity." ChemInform 28, no. 4 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199704228.

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33

Brel', V. K., and Yu I. Gudkova. "ChemInform Abstract: Synthesis of Acyclic Phosphonate Nucleotide Analogues Having a 1,3-Alkadiene Skeleton." ChemInform 43, no. 42 (September 20, 2012): no. http://dx.doi.org/10.1002/chin.201242208.

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34

Szymczak, Marzena, Agnieszka Szymańska, Jacek Stawiński, Jerzy Boryski, and Adam Kraszewski. "ArylH-Phosphonates. 14. Synthesis of New Nucleotide Analogues with Phosphonate−Phosphate Internucleosidic Linkage." Organic Letters 5, no. 20 (October 2003): 3571–73. http://dx.doi.org/10.1021/ol035166u.

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35

Katsuyama, Akira, Kousuke Sato, Fumika Yakushiji, Takanori Matsumaru, and Satoshi Ichikawa. "Solid-Phase Modular Synthesis of Park Nucleotide and Lipids I and II Analogues." Chemical and Pharmaceutical Bulletin 66, no. 1 (2018): 84–95. http://dx.doi.org/10.1248/cpb.c17-00828.

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36

Tang, Yan-bo, Zong-gen Peng, Zong-ying Liu, Yan-ping Li, Jian-dong Jiang, and Zhuo-rong Li. "Some new acyclic nucleotide analogues as antiviral prodrugs: Synthesis and bioactivities in vitro." Bioorganic & Medicinal Chemistry Letters 17, no. 22 (November 2007): 6350–53. http://dx.doi.org/10.1016/j.bmcl.2007.08.065.

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37

Cieślak, J., M. Sobkowski, J. Jankowska, M. Wenska, M. Szymczak, B. Imiolczyk, I. Zagórowska, D. Shugar, J. Stawiński, and A. Kraszewski. "Nucleoside phosphate analogues of biological interest, and their synthesis via aryl nucleoside H-phosphonates as intermediates." Acta Biochimica Polonica 48, no. 2 (June 30, 2001): 429–42. http://dx.doi.org/10.18388/abp.2001_3927.

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This review presents a brief account of the chemistry and mechanistic aspects of aryl H-phosphonates, and selected applications of this class of compounds as intermediates in the synthesis of a wide range of biologically important analogues of nucleoside phosphates, and oligonucleotides, in which the phosphate moieties are replaced by other structurally related groups. The aryl nucleoside H-phosphonates, compounds of controlled reactivity, have proven to be more versatile and superior to various mixed anhydrides as synthetic intermediates, particularly for preparation of nucleotide analogues bearing P-N or P-S bonds in various configurational arrangements at the phosphate moiety.

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38

Hocek, Michal, Milena Masojídková, and Antonín Holý. "Synthesis of Acyclic Nucleotide Analogues Derived from 2-(Aminomethyl)adenine and 2-(Aminomethyl)hypoxanthine." Collection of Czechoslovak Chemical Communications 60, no. 5 (1995): 875–82. http://dx.doi.org/10.1135/cccc19950875.

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Synthesis of a series of 2-(aminomethyl)-9-(2-phosphonomethoxyalkyl)adenines VI and hypoxanthines VII is reported. The protected 2-(aminomethyl)adenine I was selectively alkylated with [bis(2-propoxy)phosphonylmethoxy]alkyl chlorides or tosylates II and the obtained 9-[bis(2-propoxy)phosphonylmethoxy]alkyl-2-(benzyloxycarbonyla minomethyl)adenines IV were oxodeaminated to give the corresponding hypoxanthine derivatives V. The intermediates IV and V were completely deprotected by treatment with iodotrimethylsilane under formation of the title compounds VI and VII.

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39

Meerbach, A., A. Holý, P. Wutzler, E. De Clercq, and J. Neyts. "Inhibitory Effects of Novel Nucleoside and Nucleotide Analogues on Epstein—Barr Virus Replication." Antiviral Chemistry and Chemotherapy 9, no. 3 (June 1998): 275–82. http://dx.doi.org/10.1177/095632029800900309.

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The anti-Epstein–Barr virus (EBV) activity of different classes of compounds was assessed by means of an EBV DNA hybridization assay using a digoxigenin-labelled probe specific for the BamHI W fragment of the EBV genome, as well as by measuring viral capsid antigen (VCA) expression after a 7 day incubation period of P3HR-1 producer cells with the test substances. Acyclovir, ganciclovir, cidofovir and zidovudine were included as reference compounds. Several compounds proved to be potent and selective inhibitors of EBV DNA synthesis and VCA expression. Of the new compounds that were evaluated for their anti-EBV activity, the highest efficacy (lowest EC50) and highest selectivity index (SI) were shown by the purine nucleoside analogue 2-amino-7-[(1,3-dihydroxy-2-propoxy)methyl]purine (S2242) (EC50 0.6 ng/ml; SI 600), the acyclic nucleoside phosphonate analogues 9-(2-phosphonomethoxyethyl)-6-dimethylaminopurine (EC50 1.1 μg/ml; SI 91), 9-(2-phosphonomethoxyethyl)-2-amino-6-benzhydrylaminopurine (EC501.3 μg/ml; SI 29), 7-(2-phosphonomethoxyethyl)-6-dimethylaminopurine (EC50 0.8 μg/ml; SI 56), 9-( R)-(2-phosphonomethoxypropyl)-6-(2-dimethylaminoethyl)-aminopurine (EC50 0.5 μg/ml; SI 42), the 2′,3′-dideoxythymidine derivative 3′-oximino-2′,3′-dideoxythymidine (EC501.5 μg/ml; SI 65), and 1-(2,3-dideoxy-3- N-hydroxyamino-β-d-threo-pentafuran yl)pentafuranosyl)thymine (EC50 4.1 μg/ml; SI >24).

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40

Felczak, K., B. Gołos, J. M. Dzik, W. Rode, M. Bretner, D. Shugar, and T. Kulikowski. "Acyclic analogues of 5-fluoro-dUMP and 5-fluoro-2'-deoxyuridine: synthesis and inhibition of thymidylate synthase and tumour cell growth." Acta Biochimica Polonica 45, no. 1 (March 31, 1998): 75–82. http://dx.doi.org/10.18388/abp.1998_4320.

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1-[(2-Hydroxyethoxy)methyl]-5-fluorouracil (HEMFU) and 1-[(1,3-dihydroxy-2-propoxy)methyl]-5-fluorouracil (DHPFU) were prepared by alkylation of the di-O-TMS derivative of 5-fluorouracil and phosphorylated with the use of the wheat shoot phosphotransferase system to their monophosphates, HEMFUMP and DHPFUMP. 1-(2-Phosphonylmethoxyethyl)-5-fluorouracil (PMEFU) was obtained by condensation of diethyl-2-chloroethoxymethanephosphonate with 5-fluorouracil and cleavage of the alkylphosphoester with trimethylbromosilane. Inhibition of highly purified thymidylate synthase from mouse tumour Ehrlich carcinoma and leukemia L1210 cells by each of the nucleotide analogues, DHPFUMP, PMEFU and HEMFUMP, and of L5178Y mouse leukemia cell growth by the nucleoside (HEMFU) analogue, were studied. DHPFUMP proved to be the strongest inhibitor, non-competitive vs dUMP, with K(i)app 2.8 microM for time-independent interaction with the enzyme and N5,N10-methylenetetrahydrofolate (CH2H4PteGlu). In the presence of CH2H4PteGlu, DHPFUMP exhibited time-dependent inactivation of the enzyme, the inactivation rate plots being biphasic and pointing to Ki values in the microM range (10(3)-fold higher than for 5-fluoro-dUMP). HEMFUMP and PMEFU were much weaker inhibitors of the enzyme, with K(i)app values of 0.26 mM (non-competitive vs dUMP) and 30 mM (non-competitive vs dUMP), respectively. HEMFU, despite the weak interaction of its nucleotide analogue with the enzyme, proved to be a strong cell (L5178Y) growth inhibitor, with IC50 in the range 10(-5) M.

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41

Murano, Tetsuo, Yoko Yuasa, Hirokuni Kobayakawa, Tsutomu Yokomatsu, and Shiroshi Shibuya. "Synthesis of acyclic nucleotide analogues possessing a difluoromethylene phosphonyl group at the side chain." Tetrahedron 59, no. 51 (December 2003): 10223–30. http://dx.doi.org/10.1016/j.tet.2003.10.064.

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42

Stawinski, Jacek, and Renata Hiresova. "Nucleoside H-Phosphonates, XXII: Synthesis and Properties of New Nucleotide Analogues - H-Phosphonothiolate Diesters." Synlett 2007, no. 17 (September 25, 2007): 2748–52. http://dx.doi.org/10.1055/s-2007-991072.

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43

Seio, Kohji, Takuhei Miyashita, Kousuke Sato, and Mitsuo Sekine. "Synthesis and Properties of New Nucleotide Analogues Possessing Squaramide Moieties as New Phosphate Isosters." European Journal of Organic Chemistry 2005, no. 24 (December 2005): 5163–70. http://dx.doi.org/10.1002/ejoc.200500520.

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44

Scism, Robert A., and Brian O. Bachmann. "Five-Component Cascade Synthesis of Nucleotide Analogues in an Engineered Self-Immobilized Enzyme Aggregate." ChemBioChem 11, no. 1 (November 13, 2009): 67–70. http://dx.doi.org/10.1002/cbic.200900620.

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45

Coppola, Teresa, Michela Varra, Giorgia Oliviero, Aldo Galeone, Giuliana D’Isa, Luciano Mayol, Elena Morelli, et al. "Synthesis, structural studies and biological properties of new TBA analogues containing an acyclic nucleotide." Bioorganic & Medicinal Chemistry 16, no. 17 (September 2008): 8244–53. http://dx.doi.org/10.1016/j.bmc.2008.07.040.

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46

Katsuyama, Akira, Fumika Yakushiji, and Satoshi Ichikawa. "Solid-phase synthesis of fluorescent analogues of Park’s nucleotide, lipid I and lipid II." Tetrahedron Letters 73 (June 2021): 153101. http://dx.doi.org/10.1016/j.tetlet.2021.153101.

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47

Huchting, Johanna. "Targeting viral genome synthesis as broad-spectrum approach against RNA virus infections." Antiviral Chemistry and Chemotherapy 28 (January 2020): 204020662097678. http://dx.doi.org/10.1177/2040206620976786.

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Zoonotic spillover, i.e. pathogen transmission from animal to human, has repeatedly introduced RNA viruses into the human population. In some cases, where these viruses were then efficiently transmitted between humans, they caused large disease outbreaks such as the 1918 flu pandemic or, more recently, outbreaks of Ebola and Coronavirus disease. These examples demonstrate that RNA viruses pose an immense burden on individual and public health with outbreaks threatening the economy and social cohesion within and across borders. And while emerging RNA viruses are introduced more frequently as human activities increasingly disrupt wild-life eco-systems, therapeutic or preventative medicines satisfying the “one drug-multiple bugs”-aim are unavailable. As one central aspect of preparedness efforts, this review digs into the development of broadly acting antivirals via targeting viral genome synthesis with host- or virus-directed drugs centering around nucleotides, the genomes’ universal building blocks. Following the first strategy, selected examples of host de novo nucleotide synthesis inhibitors are presented that ultimately interfere with viral nucleic acid synthesis, with ribavirin being the most prominent and widely used example. For directly targeting the viral polymerase, nucleoside and nucleotide analogues (NNAs) have long been at the core of antiviral drug development and this review illustrates different molecular strategies by which NNAs inhibit viral infection. Highlighting well-known as well as recent, clinically promising compounds, structural features and mechanistic details that may confer broad-spectrum activity are discussed. The final part addresses limitations of NNAs for clinical development such as low efficacy or mitochondrial toxicity and illustrates strategies to overcome these.

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Wood, James M., Gary B. Evans, Tyler L. Grove, Steven C. Almo, Scott A. Cameron, Richard H. Furneaux, and Lawrence D. Harris. "Chemical Synthesis of the Antiviral Nucleotide Analogue ddhCTP." Journal of Organic Chemistry 86, no. 13 (June 14, 2021): 8843–50. http://dx.doi.org/10.1021/acs.joc.1c00761.

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Dvořáková, Hana, Milena Masojídková, Antonín Holý, Jan Balzarini, Graciela Andrei, Robert Snoeck, and Erik De Clercq. "Synthesis of 2‘-Aminomethyl Derivatives ofN-(2-(Phosphonomethoxy)ethyl) Nucleotide Analogues as Potential Antiviral Agents." Journal of Medicinal Chemistry 39, no. 17 (January 1996): 3263–68. http://dx.doi.org/10.1021/jm9601314.

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Amel Diab, Sonia, Antje Hienzch, Cyril Lebargy, Stéphane Guillarme, Emmanuel Pfund, and Thierry Lequeux. "Synthesis of fluorophosphonylated acyclic nucleotide analogues via copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition." Organic & Biomolecular Chemistry 7, no. 21 (2009): 4481. http://dx.doi.org/10.1039/b912724k.

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