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Original Articles

Synthesis and Biological Activity of 5‐Fluorotubercidin

, , , &
Pages 161-170 | Received 22 Aug 2003, Accepted 06 Oct 2003, Published online: 01 Jun 2007

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Jong Hyun Cho, Leda C. Bassit, Franck Amblard & Raymond F. Schinazi. (2020) Synthesis of 7-trifluoromethyl-7-deazapurine ribonucleoside analogs and their monophosphate prodrugs. Nucleosides, Nucleotides & Nucleic Acids 39:5, pages 671-687.
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Weidong Hu, Qinghua Yang, Shuyang Wang, Gang Huang, Yueteng Zhang, Jingjing Dong, Jinfeng Kang, Chuanjun Song & Junbiao Chang. (2013) A New Route for the Synthesis of 4-Amino-5-Fluoro-7-(2′-Deoxy-2′-Fluoro-2′-C-Methyl-β-d- Ribofuranosyl)-1H-Pyrrolo[2,3-D]Pyrimidine. Nucleosides, Nucleotides & Nucleic Acids 32:7, pages 389-395.
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Frank Seela, Kuiying Xu, Padmaja Chittepu & Xin Ming. (2007) Fluorinated 7-Deazapurine 2′-Deoxyribonucleosides: Modification At The Nucleobase And The Sugar Moiety. Nucleosides, Nucleotides & Nucleic Acids 26:6-7, pages 607-610.
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Frank Seela, Padmaja Chittepu, Yang He, Junlin He & Kuiying Xu. (2005) 6-AZAPYRIMIDINE AND 7-DEAZAPURINE 2′-DEOXY-2′-FLUOROARABINONUCLEOSIDES: SYNTHESIS, CONFORMATION AND PROPERTIES OF OLIGONUCLEOTIDES. Nucleosides, Nucleotides & Nucleic Acids 24:5-7, pages 847-850.
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Articles from other publishers (23)

Kjell Undheim. (2022) Nucleoside cyclic 3′,5′-phosphorothioates with purine and pyrimidine scaffolds. A chemical minireview. European Journal of Medicinal Chemistry Reports 5, pages 100037.
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Jakob Bouton, Arno Furquim d’Almeida, Louis Maes, Guy Caljon, Serge Van Calenbergh & Fabian Hulpia. (2021) Synthesis and evaluation of 3′-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents. European Journal of Medicinal Chemistry 216, pages 113290.
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Nadiia V. Pikun, Arkadij Sobolev, Aiva Plotniece, Martins Rucins, Brigita Vigante, Marina Petrova, Ruslan Muhamadejev, Karlis Pajuste & Yuriy G. Shermolovich. (2020) Synthesis of Fluorinated 3,6-Dihydropyridines and 2-(Fluoromethyl)pyridines by Electrophilic Fluorination of 1,2-Dihydropyridines with Selectfluor®. Molecules 25:14, pages 3143.
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Fabian Hulpia, Jakob Bouton, Gustavo D. Campagnaro, Ibrahim A. Alfayez, Dorien Mabille, Louis Maes, Harry P. de Koning, Guy Caljon & Serge Van Calenbergh. (2020) C6–O-alkylated 7-deazainosine nucleoside analogues: Discovery of potent and selective anti-sleeping sickness agents. European Journal of Medicinal Chemistry 188, pages 112018.
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Vincent Malnuit, Sabina Smoleń, Michal Tichý, Lenka Poštová Slavětínská & Michal Hocek. (2019) Synthesis of Cyclic and Acyclic Nucleoside Phosphonates and Sulfonamides Derived from 6‐(Thiophen‐2‐yl)‐7‐fluoro‐7‐deazapurine. European Journal of Organic Chemistry 2019:31-32, pages 5409-5423.
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Fabian Hulpia, Sam Noppen, Dominique Schols, Graciela Andrei, Robert Snoeck, Sandra Liekens, Peter Vervaeke & Serge Van Calenbergh. (2018) Synthesis of a 3′-C-ethynyl-β-d-ribofuranose purine nucleoside library: Discovery of C7-deazapurine analogs as potent antiproliferative nucleosides. European Journal of Medicinal Chemistry 157, pages 248-267.
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Pavla Perlíková & Michal Hocek. (2017) Pyrrolo[2,3‐ d ]pyrimidine (7‐deazapurine) as a privileged scaffold in design of antitumor and antiviral nucleosides . Medicinal Research Reviews 37:6, pages 1429-1460.
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Nazarii Sabat, Lenka Poštová Slavětínská, Blanka Klepetářová & Michal Hocek. (2016) C–H Phosphonation of Pyrrolopyrimidines: Synthesis of Substituted 7- and 9-Deazapurine-8-phosphonate Derivatives. The Journal of Organic Chemistry 81:19, pages 9507-9514.
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Scott J. Hughes, Tetyana Antoshchenko, Yun Chen, Hua Lu, Juan C. Pizarro & Hee-Won Park. (2016) Probing the ATP Site of GRP78 with Nucleotide Triphosphate Analogs. PLOS ONE 11:5, pages e0154862.
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Brian G. Lawhorn, Joanne Philp, Yongdong Zhao, Christopher Louer, Marlys Hammond, Mui Cheung, Harvey Fries, Alan P. Graves, Lisa Shewchuk, Liping Wang, Joshua E. Cottom, Hongwei Qi, Huizhen Zhao, Rachel Totoritis, Guofeng Zhang, Benjamin Schwartz, Hu Li, Sharon Sweitzer, Dennis A. Holt, Gregory J. GattoJr.Jr. & Lara S. Kallander. (2015) Identification of Purines and 7-Deazapurines as Potent and Selective Type I Inhibitors of Troponin I-Interacting Kinase (TNNI3K). Journal of Medicinal Chemistry 58:18, pages 7431-7448.
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Vasiliy M. Muzalevskiy, Olga V. Serdyuk & Valentine G. Nenajdenko. 2014. Fluorine in Heterocyclic Chemistry Volume 1. Fluorine in Heterocyclic Chemistry Volume 1 117 156 .
Junxing Shi, Longhu Zhou, Hongwang Zhang, Tamara R. McBrayer, Mervi A. Detorio, Melissa Johns, Leda Bassit, Megan H. Powdrill, Tony Whitaker, Steven J. Coats, Matthias Götte & Raymond F. Schinazi. (2011) Synthesis and antiviral activity of 2′-deoxy-2′-fluoro-2′-C-methyl-7-deazapurine nucleosides, their phosphoramidate prodrugs and 5′-triphosphates. Bioorganic & Medicinal Chemistry Letters 21:23, pages 7094-7098.
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Frank Seela, Simone Budow, Kuiying Xu, Xioahua Peng & Henning Eickmeier. (2011) 7-Halogenated 7-deazapurine 2′-C-methylribonucleosides. Collection of Czechoslovak Chemical Communications 76:12, pages 1413-1431.
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Petr Nauš, Pavla Perlíková, Radek Pohl & Michal Hocek. (2011) Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2′-C-methylribonucleosides, arabinonucleosides and 2′-deoxy-2′-fluoroarabinonucleosides. Collection of Czechoslovak Chemical Communications 76:8, pages 957-988.
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Petr Nauš, Radek Pohl, Ivan Votruba, Petr Džubák, Marián Hajdúch, Ria AmeralGabriel BirkušTing WangAdrian S. RayRichard MackmanTomas CihlarMichal Hocek. (2009) 6-(Het)aryl-7-Deazapurine Ribonucleosides as Novel Potent Cytostatic Agents. Journal of Medicinal Chemistry 53:1, pages 460-470.
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Kenneth L. Kirk. 2009. Fluorinated Heterocyclic Compounds. Fluorinated Heterocyclic Compounds 91 158 .
Ian T. Suydam & Scott A. Strobel. (2008) Fluorine Substituted Adenosines As Probes of Nucleobase Protonation in Functional RNAs. Journal of the American Chemical Society 130:41, pages 13639-13648.
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Peng Liu, Ashoke Sharon & Chung K. Chu. (2008) Fluorinated nucleosides: Synthesis and biological implication. Journal of Fluorine Chemistry 129:9, pages 743-766.
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Frank Seela & Kuiying Xu. (2008) 7‐Halogenated 7‐Deazapurine 2′‐Deoxyribonucleosides Related to 2′‐Deoxyadenosine, 2′‐Deoxyxanthosine, and 2′‐Deoxyisoguanosine: Syntheses and Properties. Helvetica Chimica Acta 91:6, pages 1083-1105.
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Jérôme Baudoux & Dominique Cahard. 2004. Organic Reactions. Organic Reactions 1 326 .
Frank Seela & Xin Ming. (2007) 7-Functionalized 7-deazapurine β-d and β-l-ribonucleosides related to tubercidin and 7-deazainosine: glycosylation of pyrrolo[2,3-d]pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d or β-l-ribofuranose. Tetrahedron 63:39, pages 9850-9861.
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Xiaojing Wang, Punit P. Seth, Ray Ranken, Eric E. Swayze & Migawa Michael T. Migawa Michael T.. (2004) Synthesis and Biological Activity of 5‐Fluorotubercidin.. ChemInform 35:32.
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