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

Chong Liu; Qi Chen; John D Gorden; Stewart W Schneller

doi:10.1016/j.bmc.2015.07.039

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. Epub 2015 Jul 28.

Authors

Chong Liu¹, Qi Chen¹, John D Gorden¹, Stewart W Schneller²

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: schnest@auburn.edu.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adenosine / analogs & derivatives*
Adenosine / chemical synthesis
Antiviral Agents / pharmacology*
Humans
Molecular Structure

Substances

Antiviral Agents
3-deazaneplanocin
3-deazaaristeromycin
Adenosine