Synthesis of Tubercidin, 6-Chlorotubercidin and Related Nucleosides
- 1 January 1989
- journal article
- research article
- Published by Taylor & Francis in Nucleosides, Nucleotides and Nucleic Acids
- Vol. 8 (7) , 1201-1216
- https://doi.org/10.1080/07328318908054327
Abstract
Tubercidin (7-deazaadenosine, 1a) and several 6-chlorotuber-cidin derivatives were synthesized including 4-amino-6-chloro-7-β-D-ribofuranosylpyrrolo[2,3-d]pyrimidine-3′,5′-cycyclic phosphate 9. Isolation of a side product found in the glycosylation step of the reaction sequence proved to be the N-1 ribosyl-attached isomer as shown by X-ray diffraction analysis. All derivatives were tested for in vitro antiviral and antitumor activity.This publication has 30 references indexed in Scilit:
- Synthesis and antiviral activity of certain 4- and 4,5-disubstituted 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidinesJournal of Medicinal Chemistry, 1988
- Site‐selective cyclic AMP analogs provide a new approach in the control of cancer cell growthFEBS Letters, 1987
- Pyrrolo[2,3-d]pyrimidine nucleosides as inhibitors of human cytomegalovirusAntimicrobial Agents and Chemotherapy, 1987
- Nucleic acid related compounds. 51. Synthesis and biological properties of sugar-modified analogs of the nucleoside antibiotics tubercidin, toyocamycin, sangivamycin, and formycinJournal of Medicinal Chemistry, 1987
- Antirhinovirus activity of purine nucleoside analogsAntimicrobial Agents and Chemotherapy, 1986
- Synthesis and biological activity of certain 6-substituted and 2,6-disubstituted 2'-deoxytubercidins prepared via the stereospecific sodium salt glycosylation procedureJournal of Medicinal Chemistry, 1985
- Antiviral activity of C-5 substituted tubercidin analogsJournal of Medicinal Chemistry, 1984
- Total synthesis of certain 2-, 6-mono- and 2,6-disubstituted-tubercidin derivatives. Synthesis of tubercidin via the sodium salt glycosylation procedureNucleic Acids Research, 1984
- Halogenation of tubercidin by N-halosuccinimides. A direct route to 5-bromotubercidin, a reversible inhibitor of RNA synthesis in eukaryotic cellsNucleic Acids Research, 1980
- Role of Cyclic Nucleotides in Growth ControlAnnual Review of Biochemistry, 1975