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Synthesis and biological evaluation of 2',3'-dideoxy-3'-fluororibofuranosyl purine nucleosides

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Poopeiko, NE Khripach, NB Kazimierczuk, Z Balzarini, Jan [KUL] De Clercq, Etienne [UCL] Mikhailopulo, IA

Synthesis of 9-(2,3-dideoxy-3-fluoro-beta-D-ribofuranosyl)-2-chloroadenine (7b) and -2-chloro-6-methoxypurine (9b), as well as the alpha-D-anomer 7a of the former and its N-7 isomer 10a is reported. Among the compounds synthesized, only the beta-D-anomer 7b displays moderate cytotoxic activity.

Document type Communication à un colloque (Conference Paper) – Présentation orale avec comité de sélection
Publication date 1997
Language Anglais
Conference "XII International Round Table on Nucleosides, Nucleotides and their Biological Applications - Making Drugs Out of Nucleosides and Oligonucleotides", LA JOLLA(Ca) (Sep 15-19, 1996)
Journal information "Nucleosides and Nucleotides" - Vol. 16, no. 7-9, p. 1083-1086 (1997)
Peer reviewed yes
issn 0732-8311
Publisher Marcel Dekker Inc (New York)
Affiliation UCL - MD/ESP - Ecole de santé publique
Links
  1. Plunkett William, Saunders Priscilla P., Metabolism and action of purine nucleoside analogs, 10.1016/0163-7258(91)90057-s
  2. Chidgeavadze Zurab G., Scamrov Andrei V., Beabealashvilli Robert Sh., Kvasyuk Eugenii I., Zaitseva Galina V., Mikhailopulo Igor A., Kowollik Gotthard, Langen Peter, 3'-Fluoro-2',3'-dideoxyribonucleoside 5'-triphosphates: terminators of DNA synthesis, 10.1016/0014-5793(85)80792-4
  3. Mikhailopulo Igor A., Pricota Tamara I., Poopeiko Nicolai E., Klenitskaya Tatjana V., Khripach Natalia B., Synthesis of 2′,3′-Dideoxy-3′-fluorothymidine Using Individual Anomers of 1,5-Di-O-benzoyl-2,3-dideoxy-3-fluoro-D-erythro-pentofuranose as Glycosylating Agents, 10.1055/s-1993-25925
  4. Robins Morris J., Uznański Bogdan, Nucleic acid related compounds. 33. Conversions of adenosine and guanosine to 2,6-dichloro, 2-amino-6-chloro, and derived purine nucleosides, 10.1139/v81-374
  5. Chenon Marie T., Pugmire Ronald J., Grant David M., Panzica Raymond P., Townsend Leroy B., Carbon-13 magnetic resonance. XXV. Basic set of parameters for the investigation of tautomerism in purines established from carbon-13 magnetic resonance studies using certain purines and pyrrolo[2,3-d]pyrimidines, 10.1021/ja00849a027
  6. Akhrem A. A., Mikhailopulo I. A., Abramov A. F., 13C nuclear magnetic resonance spectroscopy of selected adenine nucleosides: Structural correlation and conformation about the glycosidic bond, 10.1002/mrc.1270120416
  7. Schmidt Richard R., Lösch Gabriele R., Fischer Peter, Riburon- und Lyxuronpurinnucleosid-Derivate – Synthese, Trennung und Struktursicherung der verschiedenen Verknüpfungsisomeren, 10.1002/cber.19801130908
  8. Akhrem A. A., Dokl. Acad. Nauk SSSR, 219, 99 (1974)
  9. Herdewijn P., Pauwels R., Baba M., Balzarini J., De Clercq E., Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: a structure-activity analysis, 10.1021/jm00394a034
  10. Van Wijk, J., Huckriede, B. D., Ippel, J. H. and Altona, C. 1992.Methods in Enzymology, Edited by: Lilley, D. M.J. and Dahlberg, J. E. Vol. 211, 286–306. San Diego: Academic Press.
  11. Kalinowski, H.O., Berger, S. and Braun, S. 1984.13C-NMR Spektroskopie, 526–529. Stuttgart-New York: G. Thieme Verlag.
Bibliographic reference Poopeiko, NE ; Khripach, NB ; Kazimierczuk, Z ; Balzarini, Jan ; De Clercq, Etienne ; et. al. Synthesis and biological evaluation of 2',3'-dideoxy-3'-fluororibofuranosyl purine nucleosides.XII International Round Table on Nucleosides, Nucleotides and their Biological Applications - Making Drugs Out of Nucleosides and Oligonucleotides (LA JOLLA(Ca), Sep 15-19, 1996). In: Nucleosides and Nucleotides, Vol. 16, no. 7-9, p. 1083-1086 (1997)
Permanent URL http://hdl.handle.net/2078.1/62650