C-Nucleosides to Be Revisited

Journal of Medicinal Chemistry

Volumn 59, Issue 6, 2016, Pages 2301-2311

  De Clercq, Erik ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; BENZAMIDE DERIVATIVE; C NUCLEOSIDE; CARBOCYCLIC 4' EPIFORMYCIN; FORMYCIN; FORODESINE; GS 6620; IMMUCILLIN A; NUCLEOSIDE DERIVATIVE; PHOSPHORAMIDIC ACID DERIVATIVE; PIRAZOFURIN; PORPHYRIN; PSEUDOISOCYTIDINE; PSEUDOURIDINE; PYRAZINE DERIVATIVE; PYRAZOLO[1,5 A] 1,3,5 TRIAZINE; PYRIDINE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; SELENAZOFURIN; SHOWDOMYCIN; THIENO[3,4 D]PYRIMIDINE; TIAZOFURIN; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; 2-(4-AMINO-5H-PYRROLO(3,2-D)PYRIMIDIN-7-YL)-5-(HYDROXYMETHYL)PYRROLIDINE-3,4-DIOL; GS-6620; NUCLEOSIDE; NUCLEOTIDE; PURINE NUCLEOSIDE; TRIAZINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; DRUG SYNTHESIS; FILOVIRUS; FILOVIRUS INFECTION; HEPATITIS C; HEPATITIS C VIRUS; HUMAN; NEOPLASM; NONHUMAN; REVIEW; ANIMAL;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; HUMANS; NUCLEOSIDES; NUCLEOTIDES; PSEUDOURIDINE; PURINE NUCLEOSIDES; TRIAZINES;

EID: 84962159962     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b01157     Document Type: Review

References (102)

1. Gutowski, G. E.; Sweeney, M. J.; DeLong, D. C.; Hamill, R. L.; Gerzon, K.; Dyke, R. W. Biochemistry and biological effects of the pyrazofurins (pyrazomycins): initial clinical trial Ann. N. Y. Acad. Sci. 1975, 255, 544-551 10.1111/j.1749-6632.1975.tb29257.x
2. Warren, T. K.; Wells, J.; Panchal, R. G.; Stuthman, K. S.; Garza, N. L.; Van Tongeren, S. A.; Dong, L.; Retterer, C. J.; Eaton, B. P.; Pegoraro, G.; Honnold, S.; Bantia, S.; Kotian, P.; Chen, X.; Taubenheim, B. R.; Welch, L. S.; Minning, D. M.; Babu, Y. S.; Sheridan, W. P.; Bavari, S. Protection against filovirus diseases by a novel broad-spectrum nucleoside analogue BCX4430 Nature 2014, 508, 402-405 10.1038/nature13027
3. Cho, A.; Zhang, L.; Xu, J.; Lee, R.; Butler, T.; Metobo, S.; Aktoudianakis, V.; Lew, W.; Ye, H.; Clarke, M.; Doerffler, E.; Byun, D.; Wang, T.; Babusis, D.; Carey, A. C.; German, P.; Sauer, D.; Zhong, W.; Rossi, S.; Fenaux, M.; McHutchison, J. G.; Perry, J.; Feng, J.; Ray, A. S.; Kim, C. U. Discovery of the first C-nucleoside HCV polymerase inhibitor (GS-6620) with demonstrated antiviral response in HCV infected patients J. Med. Chem. 2014, 57, 1812-1825 10.1021/jm400201a
4. Merino, P. Chemical Synthesis of Nucleoside Analogues; John Wiley & Sons, Inc.: Hoboken, NJ, 2013.
5. Thapa, K.; Oja, T.; Metsä-Ketelä, M. Molecular evolution of the bacterial pseudouridine-5′-phosphate glycosidase protein family FEBS J. 2014, 281, 4439-4449 10.1111/febs.12950
6. Preumont, A.; Snoussi, K.; Stroobant, V.; Collet, J. F.; Van Schaftingen, E. Molecular identification of pseudouridine-metabolizing enzymes J. Biol. Chem. 2008, 283, 25238-25246 10.1074/jbc.M804122200
7. Charette, M.; Gray, M. W. Pseudouridine in RNA: what, where, how, and why IUBMB Life 2000, 49, 341-351 10.1080/152165400410182
8. Hirao, I.; Kimoto, M.; Yamakage, S.; Ishikawa, M.; Kikuchi, J.; Yokoyama, S. A unique unnatural base pair between a C analogue, pseudoisocytosine, and an A analogue, 6-methoxypurine, in replication Bioorg. Med. Chem. Lett. 2002, 12, 1391-1393 10.1016/S0960-894X(02)00184-1
9. Burchenal, J. H.; Ciovacco, K.; Kalaher, K.; O'Toole, T.; Kiefner, R.; Dowling, M. D.; Chu, C. K.; Watanabe, K. A.; Wempen, I.; Fox, J. J. Antileukemic effects of pseudoisocytidine, a new synthetic pyrimidine C-nucleoside Cancer Res. 1976, 36, 1520-1523
10. Zedeck, M. S. Incorporation of -isocytidine, a new antitumour C-nucleoside, into mammalian RNA and DNA Biochem. Pharmacol. 1979, 28, 1440-1443 10.1016/0006-2952(79)90453-2
11. Chou, T. C.; Burchenal, J. H.; Fox, J. J.; Watanabe, K. A.; Chu, C. K.; Philips, F. S. Metabolism and effects of 5-(beta-D-ribofuranosyl)isocytosine in P815 cells Cancer Res. 1979, 39, 720-728
12. Woodcock, T. M.; Chou, T. C.; Tan, C. T.; Sternberg, S. S.; Philips, F. S.; Young, C. W.; Burchenal, J. H. Biochemical, pharmacological, and phase I clinical evaluation of pseudoisocytidine Cancer Res. 1980, 40, 4243-4249
13. Gutowski, G. E.; Chaney, M. O.; Jones, N. D.; Hamill, R. L.; Davis, F. A.; Miller, R. D. Pyrazomycin B: isolation and characterization of an -C-nucleoside antibiotic related to pyrazomycin Biochem. Biophys. Res. Commun. 1973, 51, 312-317 10.1016/0006-291X(73)91258-8
14. Wenkert, E.; Hagaman, E. W.; Gutowski, G. E. Carbon-13 nuclear magnetic resonance spectral analysis of C-nucleosides. The structure of pyrazomycin B 1 Biochem. Biophys. Res. Commun. 1973, 51, 318-322 10.1016/0006-291X(73)91259-X
15. Sweeney, M. J.; Davis, F. A.; Gutowski, G. E.; Hamill, R. L.; Hoffman, D. H.; Poore, G. A. Experimental antitumor activity of pyrazomycin Cancer Res. 1973, 33, 2619-2623
16. Plagemann, P. G.; Behrens, M. Inhibition of de novo pyrimidine nucleotide and DNA synthesis and growth of cultured Novikoff rat hepatoma cells and other cell lines by pyrazofurin (NSC 143095) Cancer Res. 1976, 36, 3807-3812
17. Ohnuma, T.; Roboz, J.; Shapiro, M. L.; Holland, J. F. Pharmacological and biochemical effects of pyrazofurin in humans Cancer Res. 1977, 37, 2043-2049
18. Brockman, R. W.; Shaddix, S. C.; Rose, L. M. Biochemical aspects of chemotherapy of mouse colon carcinoma: fluoropyrimidines and pyrazofurin Cancer 1977, 40, 2681-2691 10.1002/1097-0142(197711)40:5+<2681::AID-CNCR2820400941>3.0.CO;2-E
19. Dix, D. E.; Lehman, C. P.; Jakubowski, A.; Moyer, J. D.; Handschumacher, R. E. Pyrazofurin metabolism, enzyme inhibition, and resistance in L5178Y cells Cancer Res. 1979, 39, 4485-4490
20. Suttle, D. P.; Harkrader, R. J.; Jackson, R. C. Pyrazofurin-resistant hepatoma cells deficient in adenosine kinase Eur. J. Cancer 1981, 17, 43-51 10.1016/0014-2964(81)90210-3
21. Jones, M. E. Pyrimidine nucleotide biosynthesis in animals, genes, enzymes, and regulation of UMP biosynthesis Annu. Rev. Biochem. 1980, 49, 253-279 10.1146/annurev.bi.49.070180.001345
22. McClard, R. W.; Black, M. J.; Livingstone, L. R.; Jones, M. E. Isolation and initial characterization of the single polypeptide that synthesizes uridine 5′-monophosphate from orotate in Ehrlich ascites carcinoma. Purification by tandem affinity chromatography of uridine-5′-monophosphate synthase Biochemistry 1980, 19, 4699-4706 10.1021/bi00561a024
23. Suttle, D. P. Increased levels of UMP synthase protein and mRNA in pyrazofurin-resistant rat hepatoma cells J. Biol. Chem. 1983, 258, 7707-7713
24. Scott, H. V.; Gero, A. M.; O'Sullivan, W. J. In vitro inhibition of Plasmodium falciparum by pyrazofurin, an inhibitor of pyrimidine biosynthesis de novo Mol. Biochem. Parasitol. 1986, 18, 3-15 10.1016/0166-6851(86)90045-9
25. Langley, D. B.; Shojaei, M.; Chan, C.; Lok, H. C.; Mackay, J. P.; Traut, T. W.; Guss, J. M.; Christopherson, R. I. Structure and inhibition of orotidine 5′-monophosphate decarboxylase from Plasmodium falciparum Biochemistry 2008, 47, 3842-3854 10.1021/bi702390k
26. Gardner, M. J.; Hall, N.; Fung, E.; White, O.; Berriman, M.; Hyman, R. W.; Carlton, J. M.; Pain, A.; Nelson, K. E.; Bowman, S.; Paulsen, I. T.; James, K.; Eisen, J. A.; Rutherford, K.; Salzberg, S. L.; Craig, A.; Kyes, S.; Chan, M. S.; Nene, V.; Shallom, S. J.; Suh, B.; Peterson, J.; Angiuoli, S.; Pertea, M.; Allen, J.; Selengut, J.; Haft, D.; Mather, M. W.; Vaidya, A. B.; Martin, D. M.; Fairlamb, A. H.; Fraunholz, M. J.; Roos, D. S.; Ralph, S. A.; McFadden, G. I.; Cummings, L. M.; Subramanian, G. M.; Mungall, C.; Venter, J. C.; Carucci, D. J.; Hoffman, S. L.; Newbold, C.; Davis, R. W.; Fraser, C. M.; Barrell, B. Genome sequence of the human malaria parasite Plasmodium falciparum Nature 2002, 419, 498-511 10.1038/nature01097
27. Descamps, J.; De Clercq, E. Broad-spectrum antiviral activity of pyrazofurin (pyrazomycin). In Current Chemotherapy, Proceedings of the Tenth International Congress of Chemotherap, Zürich, Switzerland, September 18-23, 1977; Siegenthaler, W.; Lüthy, R., Eds.; American Society for Microbiology, Washington, DC, 1978; pp 354-357.
28. De Clercq, E. Ebola virus (EBOV) infection: Therapeutic strategies Biochem. Pharmacol. 2015, 93, 1-10 10.1016/j.bcp.2014.11.008
29. Pattyn, S.; van der Groen, G.; Jacob, W.; Piot, P.; Courteille, G. Isolation of Marburg-like virus from a case of haemorrhagic fever in Zaire Lancet 1977, 309, 573-574 10.1016/S0140-6736(77)92002-5
30. Sidwell, R. W.; Huffman, J. H.; Khare, G. P.; Allen, L. B.; Witkowski, J. T.; Robins, R. K. Broad-spectrum antiviral activity of virazole: 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide Science 1972, 177, 705-706 10.1126/science.177.4050.705
31. Canonico, P. G.; Jahrling, P. B.; Pannier, W. L. Antiviral efficacy of pyrazofurin against selected RNA viruses Antiviral Res. 1982, 2, 331-337 10.1016/0166-3542(82)90002-X
32. Shannon, W. M. Selective inhibition of RNA tumor virus replication in vitro and evaluation of candidate antiviral agents in vivo Ann. N. Y. Acad. Sci. 1977, 284, 472-507 10.1111/j.1749-6632.1977.tb21983.x
33. De Clercq, E. Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections Clin. Microbiol. Rev. 2001, 14, 382-397 10.1128/CMR.14.2.382-397.2001
34. Kitaoka, S.; Konno, T.; De Clercq, E. Comparative efficacy of broad-spectrum antiviral agents as inhibitors of rotavirus replication in vitro Antiviral Res. 1986, 6, 57-65 10.1016/0166-3542(86)90039-2
35. Kawana, F.; Shigeta, S.; Hosoya, M.; Suzuki, H.; De Clercq, E. Inhibitory effects of antiviral compounds on respiratory syncytial virus replication in vitro Antimicrob. Agents Chemother. 1987, 31, 1225-1230 10.1128/AAC.31.8.1225
36. Hosoya, M.; Shigeta, S.; Nakamura, K.; De Clercq, E. Inhibitory effect of selected antiviral compounds on measles (SSPE) virus replication in vitro Antiviral Res. 1989, 12, 87-98 10.1016/0166-3542(89)90072-7
37. Andrei, G.; De Clercq, E. Inhibitory effect of selected antiviral compounds on arenavirus replication in vitro Antiviral Res. 1990, 14, 287-300 10.1016/0166-3542(90)90009-V
38. Jashés, M.; González, M.; López-Lastra, M.; De Clercq, E.; Sandino, A. Inhibitors of infectious pancreatic necrosis virus (IPNV) replication Antiviral Res. 1996, 29, 309-312 10.1016/0166-3542(96)80226-9
39. Morrey, J. D.; Smee, D. F.; Sidwell, R. W.; Tseng, C. Identification of active antiviral compounds against a New York isolate of West Nile virus Antiviral Res. 2002, 55, 107-116 10.1016/S0166-3542(02)00013-X
40. Lin, Y. H.; Yadav, P.; Ravatn, R.; Stollar, V. A mutant of Sindbis virus that is resistant to pyrazofurin encodes an altered RNA polymerase Virology 2000, 272, 61-71 10.1006/viro.2000.0329
41. De Clercq, E. Dancing with chemical formulae of antivirals: A panoramic view (part 2) Biochem. Pharmacol. 2013, 86, 1397-1410 10.1016/j.bcp.2013.09.010
42. Srivastava, P. C.; Pickering, M. V.; Allen, L. B.; Streeter, D. G.; Campbell, M. T.; Witkowski, J. T.; Sidwell, R. W.; Robins, R. K. Synthesis and antiviral activity of certain thiazole C-nucleosides J. Med. Chem. 1977, 20, 256-262 10.1021/jm00212a014
43. Kini, G. D.; Hennen, W. J.; Robins, R. K. Synthesis of 2-(4-amino-4-deoxy-β-D-ribofuranosyl)thiazole-4-carboxamide, a carbon-linked nucleoside with a free pyrrolidine sugar J. Org. Chem. 1986, 51, 4436-4439 10.1021/jo00373a017
44. Chiacchio, U.; Rescifina, A.; Saita, M. G.; Iannazzo, D.; Romeo, G.; Mates, J. A.; Tejero, T.; Merino, P. Zinc(II) triflate-controlled 1.; 3-dipolar cycloadditions of C-(2-thiazolyl)nitrones: application to the synthesis of a novel isoxazolidinyl analogue of tiazofurin J. Org. Chem. 2005, 70, 8991-9001 10.1021/jo051572a
45. Robins, R. K.; Srivastava, P. C.; Narayanan, V. L.; Plowman, J.; Paull, K. D. 2-beta-D-Ribofuranosylthiazole-4-carboxamide, a novel potential antitumor agent for lung tumors and metastases J. Med. Chem. 1982, 25, 107-108 10.1021/jm00344a002
46. Cooney, D. A.; Jayaram, H. N.; Gebeyehu, G.; Betts, C. R.; Kelley, J. A.; Marquez, V. E.; Johns, D. G. The conversion of 2-beta-D-ribofuranosylthiazole-4-carboxamide to an analogue of NAD with potent IMP dehydrogenase-inhibitory properties Biochem. Pharmacol. 1982, 31, 2133-2136 10.1016/0006-2952(82)90436-1
47. Jayaram, H. N.; Cooney, D. A.; Glazer, R. I.; Dion, R. L.; Johns, D. G. Mechanism of resistance to the oncolytic C-nucleoside 2-beta-D-ribofuranosylthiazole-4-carboxamide (NSC-286193) Biochem. Pharmacol. 1982, 31, 2557-2560 10.1016/0006-2952(82)90071-5
48. Jayaram, H. N.; Dion, R. L.; Glazer, R. I.; Johns, D. G.; Robins, R. K.; Srivastava, P. C.; Cooney, D. A. Initial studies on the mechanism of action of a new oncolytic thiazole nucleoside, 2-beta-D-ribofuranosylthiazole-4-carboxamide (NSC 286193) Biochem. Pharmacol. 1982, 31, 2371-2380 10.1016/0006-2952(82)90532-9
49. Jayaram, H. N.; Smith, A. L.; Glazer, R. I.; Johns, D. G.; Cooney, D. A. Studies on the mechanism of action of 2-beta-D-ribofuranosylthiazole-4-carboxamide (NSC 286193) - II. Relationship between dose level and biochemical effects in P388 leukemia in vivo Biochem. Pharmacol. 1982, 31, 3839-3845 10.1016/0006-2952(82)90300-8
50. Lui, M. S.; Faderan, M. A.; Liepnieks, J. J.; Natsumeda, Y.; Olah, E.; Jayaram, H. N.; Weber, G. Modulation of IMP dehydrogenase activity and guanylate metabolism by tiazofurin (2-beta-D-ribofuranosylthiazole-4-carboxamide) J. Biol. Chem. 1984, 259, 5078-5082
51. Shen, F.; Herenyiova, M.; Weber, G. Synergistic down-regulation of signal transduction and cytotoxicity by tiazofurin and quercetin in human ovarian carcinoma cells Life Sci. 1999, 64, 1869-1876 10.1016/S0024-3205(99)00133-2
52. Srivastava, P. C.; Robins, R. K. Synthesis and antitumor activity of 2-beta-D-ribofuranosylselenazole-4- carboxamide and related derivatives J. Med. Chem. 1983, 26, 445-448 10.1021/jm00357a024
53. Berger, N. A.; Berger, S. J.; Catino, D. M.; Petzold, S. J.; Robins, R. K. Modulation of nicotinamide adenine dinucleotide and poly(adenosine diphosphoribose) metabolism by the synthetic "C" nucleoside analogs, tiazofurin and selenazofurin. A new strategy for cancer chemotherapy J. Clin. Invest. 1985, 75, 702-709 10.1172/JCI111750
54. Gharehbaghi, K.; Sreenath, A.; Hao, Z.; Paull, K. D.; Szekeres, T.; Cooney, D. A.; Krohn, K.; Jayaram, H. N. Comparison of biochemical parameters of benzamide riboside, a new inhibitor of IMP dehydrogenase, with tiazofurin and selenazofurin Biochem. Pharmacol. 1994, 48, 1413-1419 10.1016/0006-2952(94)90565-7
55. Tricot, G. J.; Jayaram, H. N.; Lapis, E.; Natsumeda, Y.; Nichols, C. R.; Kneebone, P.; Heerema, N.; Weber, G.; Hoffman, R. Biochemically directed therapy of leukemia with tiazofurin, a selective blocker of inosine 5′-phosphate dehydrogenase activity Cancer Res. 1989, 49, 3696-3701
56. Melink, T. J.; Von Hoff, D. D.; Kuhn, J. G.; Hersh, M. R.; Sternson, L. A.; Patton, T. F.; Siegler, R.; Boldt, D. H.; Clark, G. M. Phase I evaluation and pharmacokinetics of tiazofurin (2-beta-D-ribofuranosylthiazole-4-carboxamide, NSC 286193) Cancer Res. 1985, 45, 2859-2865
57. Huggins, J. W.; Robins, R. K.; Canonico, P. G. Synergistic antiviral effects of ribavirin and the C-nucleoside analogs tiazofurin and selenazofurin against togaviruses, bunyaviruses, and arenaviruses Antimicrob. Agents Chemother. 1984, 26, 476-480 10.1128/AAC.26.4.476
58. Franchetti, P.; Marchetti, S.; Cappellacci, L.; Jayaram, H. N.; Yalowitz, J. A.; Goldstein, B. M.; Barascut, J. L.; Dukhan, D.; Imbach, J.-L.; Grifantini, M. Synthesis, conformational analysis, and biological activity of C-thioribonucleosides related to tiazofurin J. Med. Chem. 2000, 43, 1264-1270 10.1021/jm990257b
59. Franchetti, P.; Marchetti, S.; Cappellacci, L.; Yalowitz, J. A.; Jayaram, H. N.; Goldstein, B. M.; Grifantini, M. A new C-nucleoside analogue of tiazofurin: synthesis and biological evaluation of 2-beta-D-ribofuranosylimidazole-4-carboxamide (imidazofurin) Bioorg. Med. Chem. Lett. 2001, 11, 67-69 10.1016/S0960-894X(00)00594-1
60. Franchetti, P.; Cappellacci, L.; Marchetti, S.; Martini, C.; Costa, B.; Varani, K.; Borea, P. A.; Grifantini, M. C-nucleoside analogues of furanfurin as ligands to A1 adenosine receptors Bioorg. Med. Chem. 2000, 8, 2367-2373 10.1016/S0968-0896(00)00167-X
61. Bergeron-Brlek, M.; Meanwell, M.; Britton, R. Direct synthesis of imino-C-nucleoside analogues and other biologically active iminosugars Nat. Commun. 2015, 6, 6903 10.1038/ncomms7903
62. Julander, J. G.; Bantia, S.; Taubenheim, B. R.; Minning, D. M.; Kotian, P.; Morrey, J. D.; Smee, D. F.; Sheridan, W. P.; Babu, Y. S. BCX4430, a novel nucleoside analog, effectively treats yellow fever in a hamster model Antimicrob. Agents Chemother. 2014, 58, 6607-6614 10.1128/AAC.03368-14
63. Evans, G. B.; Furneaux, R. H.; Hutchison, T. L.; Kezar, H. S.; Morris, P. E., Jr.; Schramm, V. L.; Tyler, P. C. Addition of lithiated 9-deazapurine derivatives to a carbohydrate cyclic imine: convergent synthesis of the aza-C-nucleoside immucillins J. Org. Chem. 2001, 66, 5723-5730 10.1021/jo0155613
64. Evans, G. B.; Furneaux, R. H.; Hausler, H.; Larsen, J. S.; Tyler, P. C. Imino-C-nucleoside synthesis: heteroaryl lithium carbanion additions to a carbohydrate cyclic imine and nitrone J. Org. Chem. 2004, 69, 2217-2220 10.1021/jo035744k
65. Kicska, G. A.; Long, L.; Hörig, H.; Fairchild, C.; Tyler, P. C.; Furneaux, R. H.; Schramm, V. L.; Kaufman, H. L. Immucillin H, a powerful transition-state analog inhibitor of purine nucleoside phosphorylase, selectively inhibits human T lymphocytes Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 4593-4598 10.1073/pnas.071050798
66. Cho, A.; Saunders, O. L.; Butler, T.; Zhang, L.; Xu, J.; Vela, J. E.; Feng, J. Y.; Ray, A. S.; Kim, C. U. Synthesis and antiviral activity of a series of 1′-substituted 4-aza-7,9-dideazaadenosine C-nucleosides Bioorg. Med. Chem. Lett. 2012, 22, 2705-2707 10.1016/j.bmcl.2012.02.105
67. Olsen, D. B.; Eldrup, A. B.; Bartholomew, L.; Bhat, B.; Bosserman, M. R.; Ceccacci, A.; Colwell, L. F.; Fay, J. F.; Flores, O. A.; Getty, K. L.; Grobler, J. A.; LaFemina, R. L.; Markel, E. J.; Migliaccio, G.; Prhavc, M.; Stahlhut, M. W.; Tomassini, J. E.; MacCoss, M.; Hazuda, D. J.; Carroll, S. S. A 7-deaza-adenosine analog is a potent and selective inhibitor of hepatitis C virus replication with excellent pharmacokinetic properties Antimicrob. Agents Chemother. 2004, 48, 3944-3953 10.1128/AAC.48.10.3944-3953.2004
68. De Clercq, E.; Balzarini, J.; Madej, D.; Hansske, F.; Robins, M. J. Nucleic acid related compounds. 51. Synthesis and biological properties of sugar-modified analogues of the nucleoside antibiotics tubercidin, toyocamycin, sangivamycin, and formycin J. Med. Chem. 1987, 30, 481-486 10.1021/jm00386a007
69. Patil, S. A.; Otter, B. A.; Klein, R. S. 4-Aza-7,9-dideazaadenosine, a new cytotoxic synthetic C-nucleoside analogue of adenosine Tetrahedron Lett. 1994, 35, 5339-5342 10.1016/S0040-4039(00)73494-0
70. Butora, G.; Olsen, D. B.; Carroll, S. S.; McMasters, D. R.; Schmitt, C.; Leone, J. F.; Stahlhut, M.; Burlein, C.; Maccoss, M. Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2′-C-methyladenosine Bioorg. Med. Chem. 2007, 15, 5219-5229 10.1016/j.bmc.2007.05.020
71. Cho, A.; Zhang, L.; Xu, J.; Babusis, D.; Butler, T.; Lee, R.; Saunders, O. L.; Wang, T.; Parrish, J.; Perry, J.; Feng, J. Y.; Ray, A. S.; Kim, C. U. Synthesis and characterization of 2′-C-Me branched C-nucleosides as HCV polymerase inhibitors Bioorg. Med. Chem. Lett. 2012, 22, 4127-4132 10.1016/j.bmcl.2012.04.065
72. Mish, M. R.; Cho, A.; Kirschberg, T.; Xu, J.; Zonte, C. S.; Fenaux, M.; Park, Y.; Babusis, D.; Feng, J. Y.; Ray, A. S.; Kim, C. U. Preparation and biological evaluation of 1′-cyano-2′-C-methyl pyrimidine nucleosides as HCV NS5B polymerase inhibitors Bioorg. Med. Chem. Lett. 2014, 24, 3092-3095 10.1016/j.bmcl.2014.05.015
73. Draffan, A. G.; Frey, B.; Fraser, B. H.; Pool, B.; Gannon, C.; Tyndall, E. M.; Cianci, J.; Harding, M.; Lilly, M.; Hufton, R.; Halim, R.; Jahangiri, S.; Bond, S.; Jeynes, T. P.; Nguyen, V. T.; Wirth, V.; Luttick, A.; Tilmanis, D.; Pryor, M.; Porter, K.; Morton, C. J.; Lin, B.; Duan, J.; Bethell, R. C.; Kukolj, G.; Simoneau, B.; Tucker, S. P. Derivatives of imidazotriazine and pyrrolotriazine C-nucleosides as potential new anti-HCV agents Bioorg. Med. Chem. Lett. 2014, 24, 4984-4988 10.1016/j.bmcl.2014.09.030
74. Tyndall, E. M.; Draffan, A. G.; Frey, B.; Pool, B.; Halim, R.; Jahangiri, S.; Bond, S.; Wirth, V.; Luttick, A.; Tilmanis, D.; Thomas, J.; Porter, K.; Tucker, S. P. Prodrugs of imidazotriazine and pyrrolotriazine C-nucleosides can increase anti-HCV activity and enhance nucleotide triphosphate concentrations in vitro Bioorg. Med. Chem. Lett. 2015, 25, 869-873 10.1016/j.bmcl.2014.12.069
75. Draffan, A. G.; Frey, B.; Pool, B.; Gannon, C.; Tyndall, E. M.; Lilly, M.; Francom, P.; Hufton, R.; Halim, R.; Jahangiri, S.; Bond, S.; Nguyen, V. T.; Jeynes, T. P.; Wirth, V.; Luttick, A.; Tilmanis, D.; Thomas, J. D.; Pryor, M.; Porter, K.; Morton, C. J.; Lin, B.; Duan, J.; Kukolj, G.; Simoneau, B.; McKercher, G.; Lagacé, L.; Amad, M.; Bethell, R. C.; Tucker, S. P. Discovery and synthesis of C-nucleosides as potential new anti-HCV agents ACS Med. Chem. Lett. 2014, 5, 679-684 10.1021/ml500077j
76. Feng, J. Y.; Cheng, G.; Perry, J.; Barauskas, O.; Xu, Y.; Fenaux, M.; Eng, S.; Tirunagari, N.; Peng, B.; Yu, M.; Tian, Y.; Lee, Y. J.; Stepan, G.; Lagpacan, L. L.; Jin, D.; Hung, M.; Ku, K. S.; Han, B.; Kitrinos, K.; Perron, M.; Birkus, G.; Wong, K. A.; Zhong, W.; Kim, C. U.; Carey, A.; Cho, A.; Ray, A. S. Inhibition of hepatitis C virus replication by GS-6620, a potent C-nucleoside monophosphate prodrug Antimicrob. Agents Chemother. 2014, 58, 1930-1942 10.1128/AAC.02351-13
77. Murakami, E.; Wang, T.; Babusis, D.; Lepist, E. I.; Sauer, D.; Park, Y.; Vela, J. E.; Shih, R.; Birkus, G.; Stefanidis, D.; Kim, C. U.; Cho, A.; Ray, A. S. Metabolism and pharmacokinetics of the anti-hepatitis C virus nucleotide prodrug GS-6620 Antimicrob. Agents Chemother. 2014, 58, 1943-1951 10.1128/AAC.02350-13
78. Coats, S. J.; Garnier-Amblard, E. C.; Amblard, F.; Ehteshami, M.; Amiralaei, S.; Zhang, H.; Zhou, L.; Boucle, S. R.; Lu, X.; Bondada, L.; Shelton, J. R.; Li, H.; Liu, P.; Li, C.; Cho, J. H.; Chavre, S. N.; Zhou, S.; Mathew, J.; Schinazi, R. F. Chutes and ladders in hepatitis C nucleoside drug development Antiviral Res. 2014, 102, 119-147 10.1016/j.antiviral.2013.11.008
79. Matsumoto, S. S.; Fujihaki, J. M.; Nord, L. D.; Willis, R. C.; Lee, V. M.; Sharma, B. S.; Sanghvi, Y. S.; Kini, G. D.; Revankar, G. R.; Robins, R. K.; Jolley, W. B.; Smith, R. A. Inhibition of pyrimidine metabolism in myeloid leukemia cells by triazole and pyrazole nucleosides Biochem. Pharmacol. 1990, 39, 455-462 10.1016/0006-2952(90)90050-U
80. Walker, J. A., II; Liu, W.; Wise, D. S.; Drach, J. C.; Townsend, L. B. Synthesis and antiviral evaluation of certain novel pyrazinoic acid C-nucleosides J. Med. Chem. 1998, 41, 1236-1241 10.1021/jm970532z
81. Gharehbaghi, K.; Grünberger, W.; Jayaram, H. N. Studies on the mechanism of action of benzamide riboside: a novel inhibitor of IMP dehydrogenase Curr. Med. Chem. 2002, 9, 743-748 10.2174/0929867024606902
82. Redpath, P.; Macdonald, S.; Migaud, M. E. A regio- and stereocontrolled approach to pyranosyl C-nucleoside synthesis Org. Lett. 2008, 10, 3323-3326 10.1021/ol801183e
83. Urban, M.; Pohl, R.; Klepetářová, B.; Hocek, M. New modular and efficient approach to 6-substituted pyridin-2-yl C-nucleosides J. Org. Chem. 2006, 71, 7322-7328 10.1021/jo061080d
84. Joubert, N.; Pohl, R.; Klepetéřová, B.; Hocek, M. Modular and practical synthesis of 6-substituted pyridin-3-yl C-nucleosides J. Org. Chem. 2007, 72, 6797-6805 10.1021/jo0709504
85. Fraley, A. W.; Chen, D.; Johnson, K.; McLaughlin, L. W. An HIV reverse transcriptase-selective nucleoside chain terminator J. Am. Chem. Soc. 2003, 125, 616-617 10.1021/ja020639y
86. Aketani, S.; Tanaka, K.; Yamamoto, K.; Ishihama, A.; Cao, H.; Tengeiji, A.; Hiraoka, S.; Shiro, M.; Shionoya, M. Syntheses and structure-activity relationships of nonnatural beta-C-nucleoside 5′-triphosphates bearing an aromatic nucleobase with phenolic hydroxy groups: inhibitory activities against DNA polymerases J. Med. Chem. 2002, 45, 5594-5603 10.1021/jm020193w
87. Schweitzer, B. A.; Kool, E. T. Aromatic nonpolar nucleosides as hydrophobic isosteres of pyrimidine and purine nucleosides J. Org. Chem. 1994, 59, 7238-7242 10.1021/jo00103a013
88. Moran, S.; Ren, R. X.; Kool, E. T. A thymidine triphosphate shape analog lacking Watson-Crick pairing ability is replicated with high sequence selectivity Proc. Natl. Acad. Sci. U. S. A. 1997, 94, 10506-10511 10.1073/pnas.94.20.10506
89. Khalili, P.; Naimi, E.; Knaus, E. E.; Wiebe, L. I. Pharmacokinetics and metabolism of the novel synthetic C-nucleoside, 1-(2-deoxy-beta-D-ribofuranosyl)-2,4-difluoro-5-iodobenzene: a potential mimic of 5-iodo-2′-deoxyuridine Biopharm. Drug Dispos. 2002, 23, 105-113 10.1002/bdd.301
90. Bonnac, L.; Lee, S. E.; Giuffredi, G. T.; Elphick, L. M.; Anderson, A. A.; Child, E. S.; Mann, D. J.; Gouverneur, V. Synthesis and O-phosphorylation of 3,3,4,4-tetrafluoroaryl-C-nucleoside analogues Org. Biomol. Chem. 2010, 8, 1445-1454 10.1039/b922442d
91. Lu, J.; Li, N. S.; Koo, S. C.; Piccirilli, J. A. Synthesis of pyridine, pyrimidine and pyridinone C-nucleoside phosphoramidites for probing cytosine function in RNA J. Org. Chem. 2009, 74, 8021-8030 10.1021/jo9016919
92. Kaufmann, M.; Gisler, M.; Leumann, C. J. Stable cyclohexyl-phenyl recognition in the center of a DNA duplex Angew. Chem., Int. Ed. 2009, 48, 3810-3813 10.1002/anie.200900153
93. Rabinowitz, M.; Uehara, Y.; Vistica, D. T. Differential competition with cytotoxic agents: an approach to selectivity in cancer chemotherapy Science 1979, 206, 1085-1087 10.1126/science.493993
94. Uehara, Y.; Fisher, J. M.; Rabinovitz, M. Showdomycin and its reactive moiety, maleimide. A comparison in selective toxicity and mechanism of action in vitro Biochem. Pharmacol. 1980, 29, 2199-2204 10.1016/0006-2952(80)90198-7
95. Trost, B. M.; Kallander, L. S. A versatile enantioselective strategy toward L-C-nucleosides: A total synthesis of L-Showdomycin J. Org. Chem. 1999, 64, 5427-5435 10.1021/jo990195x
96. Plagemann, P. G. W.; Woffendin, C. Use of formycin B as a general substrate for measuring facilitated nucleoside transport in mammalian cells Biochim. Biophys. Acta, Mol. Cell Res. 1989, 1010, 7-15 10.1016/0167-4889(89)90177-8
97. Zhou, J.; Yang, M.; Akdag, A.; Wang, H.; Schneller, S. W. Carbocyclic 4-epiformycin Tetrahedron 2008, 64, 433-438 10.1016/j.tet.2007.10.054
98. Hamann, M.; Pierra, C.; Sommadossi, J. P.; Musiu, C.; Vargiu, L.; Liuzzi, M.; Storer, R.; Gosselin, G. Synthesis and antiviral evaluation of thieno[3,4-d]pyrimidine C-nucleoside analogues of 2′,3′-dideoxy- and 2′,3′-dideoxy-2′,3′-didehydro-adenosine and -inosine Bioorg. Med. Chem. 2009, 17, 2321-2326 10.1016/j.bmc.2009.02.011
99. Lefoix, M.; Mathis, G.; Kleinmann, T.; Truffert, J. C.; Asseline, U. Pyrazolo[1,5-a]-1,3,5-triazine C-nucleoside as deoxyadenosine analogue: synthesis, pairing, and resistance to hydrolysis J. Org. Chem. 2014, 79, 3221-3227 10.1021/jo5000253
100. Zhang, F.; Mu, D.; Wang, L.; Du, P.; Han, F.; Zhao, Y. Synthesis of substituted mono- and diindole C-nucleoside analogues from sugar terminal alkynes by sequential sonogashira/heteroannulation reaction J. Org. Chem. 2014, 79, 9490-9499 10.1021/jo501488x
101. Morales-Rojas, H.; Kool, E. T. A porphyrin C-nucleoside incorporated into DNA Org. Lett. 2002, 4, 4377-4380 10.1021/ol0267376
102. St. Vincent, M. R.; Colpitts, C. C.; Ustinov, A. V.; Muqadas, M.; Joyce, M. A.; Barsby, N. L.; Epand, R. F.; Epand, R. M.; Khramyshev, S. A.; Valueva, O. A.; Korshun, V. A.; Tyrrell, D. L.; Schang, L. M. Rigid amphipathic fusion inhibitors, small molecule antiviral compounds against enveloped viruses Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 17339-17344 10.1073/pnas.1010026107