title: Synthesis and antiviral activities of 3-deaza-3-fluoroaristeromycin and its 5' analogues.
abstract: The naturally occurring adenine based carbocyclic nucleosides aristeromycin and neplanocin A and their 3-deaza analogues have found a prominent place in the search for diverse antiviral activity agent scaffolds because of their ability to inhibit S-adenosylhomocysteine (AdoHcy) hydrolase. Following the lead of these compounds, their 3-deaza-3-fluoroaristeromycin analogues have been synthesized and their effect on S-adenosylhomocysteine hydrolase and RNA and DNA viruses determined.
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: Chong
authors.initials: C
authors.lastname: Liu
authors.affiliation: Microbiotix, Inc., One Innovation Drive, Worcester, MA 01605, United States.
authors.forename: Gloria
authors.initials: G
authors.lastname: Komazin
authors.affiliation: Microbiotix, Inc., One Innovation Drive, Worcester, MA 01605, United States.
authors.forename: Terry L
authors.initials: TL
authors.lastname: Bowlin
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: D043383:Adenosylhomocysteinase / Q000037:antagonists & inhibitors / Q000378:metabolism; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D002522:Chlorocebus aethiops; D004267:DNA Viruses / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D057809:HEK293 Cells; D006801:Humans; D012328:RNA Viruses / Q000187:drug effects; D012435:S-Adenosylhomocysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D014709:Vero Cells
chemical_list: D000998:Antiviral Agents; D004791:Enzyme Inhibitors; D012435:S-Adenosylhomocysteine; D043383:Adenosylhomocysteinase
keywords: 3-Deazaaristeromycin; AdoHcy hydrolase; Carbocyclic nucleosides; Measles; Mitsunobu coupling; Monkeypox