title: Enantiomeric 3-deaza-1',6'-isoneplanocin and its 3-bromo analogue: Synthesis by the Ullmann reaction and their antiviral properties.
abstract: The 1',6'-isomer of neplanocin A possesses biological properties that have not been optimised through rationally conceived analogues. In that direction, this Letter reports the use of the Ullmann reaction to achieve enantiomeric 3-deaza-1',6'-isoneplanocin and 3-bromo-3-deaza-1',6'-isoneplanocin. These four compounds showed significant Ebola activity that is not specifically due to their inhibition of S-adenonosylhomocysteine hydrolase, as might have been expected for 3-deazaadenine carbocyclic nucleosides. For some members of this group, antiviral activity was also found against human cytomegalovirus, hepatitis B, norovirus, and measles.
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: Department of Chemistry, Slippery Rock University, Slippery Rock, PA 16057, 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. Electronic address: schnest@auburn.edu.
authors.forename: Stewart W
authors.initials: SW
authors.lastname: Schneller
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives / Q000737:chemistry; D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D043383:Adenosylhomocysteinase / Q000037:antagonists & inhibitors / Q000378:metabolism; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D003587:Cytomegalovirus / Q000187:drug effects; D029043:Ebolavirus / Q000187:drug effects; D006801:Humans; D018103:Morbillivirus / Q000187:drug effects; D029322:Norovirus / Q000187:drug effects; D009705:Nucleosides / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000998:Antiviral Agents; D009705:Nucleosides; C055133:3-deazaadenine; C031096:neplanocin A; D043383:Adenosylhomocysteinase; D000225:Adenine; D000241:Adenosine
keywords: 3-Deaza-1′,6′-isoneplanocin; Antiviral; Carbocyclic nucleosides; Ullmann reaction