ORGN 656 |
| 3-Deaza-guanosine has been studied extensively and it was shown to display broad-spectrum antiviral activity against various DNA and RNA virus, as well as antitumor activity. It is well known in the literature that introduction of one or more fluorine atoms to biologically active compounds can increase its bioavailability, liphopilicity and bioactivity. Although, Matsuda and coworkers first synthesized 3-fluoro-3-deaza-guanosine in 1999, biological properties of this important molecule is not well explored due to the high complexity in the chemical synthesis and difficulties in obtaining substantial quantity. In order to simplify and generalize the synthesis of 3-fluoro-3-deaza-purine nucleosides with different sugar modifications, we envisioned the synthesis as shown in Scheme using electrophilic fluorination as a key reaction on 5-cyanomethylimidazole 4-carboxylate nucleosides. As a result of this envision, we wish to report general, convenient and facile methodology for the synthesis of 3-fluoro-3-deaza-G nucleosides exploring the advantage of electrophilic fluorination reaction.
|
|
Proteins, Peptides, and Nucleotides
8:00 AM-11:00 AM, Wednesday, 16 March 2005 Convention Center -- Room 9, Oral
Division of Organic Chemistry |
