Abstract |
Treatment of 3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-oxothymidine (4) with potassium or magnesium nitromethanide afforded in good yield the resolvable epimeric mixture of the expected blocked nitronucleosides 5 which upon dehydration led to the corresponding E-nitroenofuranosylthymidine 6. Nucleophilic attack of cyanide onto the nitrovinyl group led to a nucleoside analogue bearing a terminal 1-cyanovinyl group (7), a soft electrophilic group which, upon reaction with benzeneselenol, underwent a conjugate addition to the phenylselenonucleoside derivative 9. All these compounds, eventually de-O-silylated, were subject of in vitro biological testing, some exhibiting interesting cytotoxic or antiviral properties.
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Authors | J M Tronchet, I Kovacs, P Dilda, M Seman, G Andrei, R Snoeck, E De Clercq, J Balzarini |
Journal | Nucleosides, nucleotides & nucleic acids
(Nucleosides Nucleotides Nucleic Acids)
Vol. 20
Issue 12
Pg. 1927-39
(Dec 2001)
ISSN: 1525-7770 [Print] United States |
PMID | 11794798
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- 3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-oxothymidine
- Anti-HIV Agents
- Silanes
- Thymidine
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Topics |
- Animals
- Anti-HIV Agents
(chemical synthesis, pharmacology)
- Biochemistry
(methods)
- Cell Division
(drug effects)
- Drug Evaluation, Preclinical
- Humans
- Inhibitory Concentration 50
- Mice
- Microbial Sensitivity Tests
- Silanes
(chemical synthesis, pharmacology)
- Structure-Activity Relationship
- Thymidine
(analogs & derivatives, chemical synthesis, chemistry, pharmacology)
- Tumor Cells, Cultured
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