title: 2- and 3-Fluoro-3-deazaneplanocins, 2-fluoro-3-deazaaristeromycins, and 3-methyl-3-deazaneplanocin: Synthesis and antiviral properties.
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.
authors.affiliation: Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, United States.
authors.forename: Chong
authors.initials: C
authors.lastname: Liu
authors.affiliation: Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, United States.
authors.forename: Qi
authors.initials: Q
authors.lastname: Chen
authors.affiliation: Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, United States.
authors.forename: John D
authors.initials: JD
authors.lastname: Gorden
authors.affiliation: Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, United States. Electronic address: schnest@auburn.edu.
authors.forename: Stewart W
authors.initials: SW
authors.lastname: Schneller
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000998:Antiviral Agents / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure
chemical_list: D000998:Antiviral Agents; C048460:3-deazaneplanocin; C034583:3-deazaaristeromycin; D000241:Adenosine
keywords: Antiviral activity; Carbocyclic nucleosides; Fluoro 3-deazaadenine nucleosides