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85033840032
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note
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In the text, the naming and numbering of the 1′,2′-seconucleophosphonates follow nucleoside nomenclature; however, in the Experimental Section, the acyclic side chains of the title compounds are named and numbered in accordance with Chemical Abstracts Service nomenclature.
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6
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5-Phosphoribosyl 1-Pyrophosphate Synthetase converts the Acyclic Nucleoside Phosphonates 9-(3-Hydroxy-2-phosphonylmethoxypropyl)- Adenine and 9-(2-Phosphonylmethoxyethyl)adenine directly to their Antivirally Active Diphosphate Derivatives
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Brodfuehrer, P.R.1
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9
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0025247710
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Acyclic Purine Phosphonate Analogues as Antiviral Agents. Synthesis and Structure-Activity Relationships
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Toronto, Canada, June MEDI 17
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Vemishetti, P.1
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An Enantiospecific Synthesis of the Human Cytomegalovirus Antiviral Agent [(R)-3-((2-Amino-1,6-dihydro-6-oxo-9H-purine-9-yl)methoxy)-4-hydroxybutyl] phosphonic Acid
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This synthetic approach was recently used in the preparation of the R-enantiomer of ganciclovir phosphonate; see: Chamberlain, S. D.; Biron, K. K.; Dornsife, R. E.; Averett, D. R.; Beauchamp, L.; Koszalka, G. W. An Enantiospecific Synthesis of the Human Cytomegalovirus Antiviral Agent [(R)-3-((2-Amino-1,6-dihydro-6-oxo-9H-purine-9-yl)methoxy)-4-hydroxybutyl] phosphonic Acid. J. Med. Chem. 1994, 37, 1371-1377.
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15
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The Preparation of Chiral Butanetriols and -tetrols
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(a) Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C.-J.; Racha, S.; Panzica, R. P. The Preparation of Chiral Butanetriols and -tetrols. J. Org. Chem. 1988, 53, 2598-2602.
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(a) Vemishetti, P.; Leiby, R. W.; Abushanab, E.; Panzica, R. P. A Practical Synthesis of Ethyl 1,2,4-Triazole-3-Carboxylate and its use in the Formation of Chiral 1′,2′-Seconucleosides of Ribavirin. J. Heterocycl. Chem. 1988, 25, 651-654.
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0025122141
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Preparation of 2′-Deoxy-2′-fluoro-1′,2′-seconucleosides as Potential Antiviral Agents
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(b) Vemishetti, P.; Saibaba, R.; Panzica, R. P.; Abushanab, E. Preparation of 2′-Deoxy-2′-fluoro-1′,2′-seconucleosides as Potential Antiviral Agents. J. Med. Chem. 1990, 33, 681-686.
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Synthesis of Racemic 2-Phosphonomethyl-1,3,-dixoloane Nucleoside Analogues as Potential Antiviral Agents
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Bednarski, K.; Dixit, D. M.; Mansour, T. S.; Colman, S. G.; Walcott, S. M.; Ashman, C. Synthesis of Racemic 2-Phosphonomethyl-1,3,-dixoloane Nucleoside Analogues as Potential Antiviral Agents. Bioorg. Med. Chem. Lett. 1995, 5, 1741-1744.
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23
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85033840359
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note
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2N protons were not completely visible due to overlap with the HDO peak.
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24
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0020633883
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Broad-Spectrum Antiviral Activity of 2-β-D-Ribofuranosyl-4-Carboxamide, a New Antiviral Agent
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Kirsi, J. J.; North, J. A.; McKernan, P. A.; Murray, B. K.; Canonico, P. G.; Huggins, J. W.; Srivastava, P. C.; Robins, R. K. Broad-Spectrum Antiviral Activity of 2-β-D-Ribofuranosyl-4-Carboxamide, a New Antiviral Agent. Antimicrob. Agents Chemother. 1983, 24, 353-361.
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Huggins, J.W.6
Srivastava, P.C.7
Robins, R.K.8
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25
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0021188176
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Broad-Spectrum Synergistic Antiviral Activity of Selenazofurin and Ribavirin
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26
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0021168019
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Synergistic Antiviral Effects of Ribavirin and the C-Nucleoside Analogs Tiazofurin and Seleazofurin Against Togaviruses, Bunyaviruses, and Arenaviruses
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Huggins, J. W.; Robins, R. K.; Canonico, P. G. Synergistic Antiviral Effects of Ribavirin and the C-Nucleoside Analogs Tiazofurin and Seleazofurin Against Togaviruses, Bunyaviruses, and Arenaviruses. Antimicrob. Agents Chemother. 1984, 26, 476-480.
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Huggins, J.W.1
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27
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85033840406
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note
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Testing was conducted under the auspices of USAMRIID.
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