title: The enantiomers of the 1',6'-isomer of neplanocin A: synthesis and antiviral properties.
abstract: Both enantiomers of 1',6'-isoneplanocin have been prepared from a common substituted cyclopentane epoxide in 7 steps. Both compounds were subjected to DNA and RNA viral assessments with moderate to high activity found for both towards human cytomegalovirus, measles, Ebola, norovirus, and dengue. The D-like congener also showed vaccinia and HBV effectiveness. In many of the other antiviral assays both compounds showed cytotoxicity making, in some cases, an EC50 determination not possible. The S-adenosylhomocysteine hydrolase inhibitory effects showed the D-like target to be equal that of neplanocin itself and better than 3-deazaneplanocin whereas the L-like analogue was 13 to 30 times less inhibitory than 3-deazaneplanocin and neplanocin, respectively.
authors.affiliation: Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, United States.
authors.forename: Wei
authors.initials: W
authors.lastname: Ye
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 / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D003587:Cytomegalovirus / Q000187:drug effects; D003716:Dengue Virus / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D029043:Ebolavirus / Q000187:drug effects; D006515:Hepatitis B virus / Q000187:drug effects; D008459:Measles virus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D029322:Norovirus / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014616:Vaccinia virus / Q000187:drug effects
chemical_list: D000998:Antiviral Agents; C031096:neplanocin A; D000241:Adenosine
keywords: Carbocyclic nucleosides; Common precursor to two enantiomeric isoneplanocins; DNA and RNA viruses; S-Adenosylhomocysteine hydrolase