2. Academic Validation
  3. l-like 3-deazaneplanocin analogues: Synthesis and antiviral properties

l-like 3-deazaneplanocin analogues: Synthesis and antiviral properties

  • Bioorg Med Chem Lett. 2019 Oct 1;29(19):126613. doi: 10.1016/j.bmcl.2019.08.017.
Qi Chen 1,  Alexander Smith 2
Affiliations

Affiliations

  • 1 Department of Chemistry, Slippery Rock University, Slippery Rock, PA 16057, United States. Electronic address: [email protected].
  • 2 Department of Chemistry, Slippery Rock University, Slippery Rock, PA 16057, United States.
PMID: 31431358 DOI: 10.1016/j.bmcl.2019.08.017
Abstract

The potent Antiviral properties of 3-deazaneplanocin, 3-deaza-isoneplanocins (1) and recently discovered l-like carbocyclic nucleosides (2, 3 and 4) prompted us to pursue rationally conceived l-like 3-deazaneplanocin analogues. The synthesis of those analogues including l-like 3-deazaneplanocin (5), l-like 3-bromo-3-deazaneplanocin (6), and l-like 5'-fluoro-5'-deoxy-3-deazaneplanocin (7), was accomplished from a common intermediate, (-)-cyclopentenone (8). Antiviral analysis found 5 and 6 to display favorable activity against the Ebola virus, as expected for 3-deazaadenine carbocyclic nucleosides. Compound 5 also showed activity against arenaviruses, including Pinchinde and Tacaribe.

Keywords

3-Deazaneplanocin; Anti-Ebola; Antiviral; Carbocyclic nucleosides; l-like nucleosides.

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