2- and 3-Fluoro-3-deazaneplanocins, 2-fluoro-3-deazaaristeromycins, and 3-methyl-3-deazaneplanocin: Synthesis and antiviral properties

  • Bioorg Med Chem. 2015 Sep 1;23(17):5496-501. doi: 10.1016/j.bmc.2015.07.039.
Chong Liu  1 ,  Qi Chen  1 ,  John D Gorden  1 ,  Stewart W Schneller  2
Affiliations
  • 1. Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, United States.
  • 2. Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, United States. Electronic address: [email protected].
PMID: 26260336 DOI: 10.1016/j.bmc.2015.07.039
Abstract

The 3-deaza analogs of the naturally occurring adenine-based carbocyclic nucleosides aristeromycin and neplanocin possess biological properties that have not been optimized. In that direction, this paper reports the strategic placement of a fluorine atom at the C-2 and C-3 positions and a methyl at the C-3 site of the 3-deazaadenine ring of the aforementioned compounds. The synthesis and S-adenosylhomocysteine hydrolase inhibitory and Antiviral properties of these targets are described. Some, but not all, compounds in this series showed significant activity toward herpes, arena, bunya, flavi, and orthomyxoviruses.

Keywords
Antiviral activity; Carbocyclic nucleosides; Fluoro 3-deazaadenine nucleosides.