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ID: ALA4396935

Journal: Bioorg Med Chem Lett

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

Authors: Chen Q, Smith A.

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.

CiteXplore: 31431358

DOI: 10.1016/j.bmcl.2019.08.017