Antiviral enantiomeric preference for 5'-noraristeromycin

J Med Chem. 1994 Feb 18;37(4):551-4. doi: 10.1021/jm00030a014.

Abstract

In order to determine if the potent antiviral properties of (+/-)-5'-noraristeromycin reside in one of its enantiomers, an analysis of each enantiomer has been carried out. A five-step route to the (+)-stereoisomer is described from (+)-(1R,4S)-4-hydroxy-2-cyclopenten-1-yl acetate, whereas the synthesis of the (-)-enantiomer had been reported previously from the same starting material. The (-)-2 and (+)-2 enantiomers were evaluated for antiviral activity against a large number of viruses and found to display an antiviral activity spectrum characteristic of (S)-adenosyl-L-homocysteine hydrolase inhibitors. The (-)-enantiomer retained the significant anticytomegalovirus properties previously reported for the racemic 2 and was, on the average, 10-fold more potent than (+)-2 in inhibiting virus replication, tumor cell growth, and (S)-adenosyl-L-homocysteine hydrolase activity.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / pharmacology
  • Adenosylhomocysteinase
  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology*
  • Humans
  • Hydrolases / antagonists & inhibitors
  • Leukemia L1210 / drug therapy
  • Mice
  • Microbial Sensitivity Tests
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tumor Cells, Cultured / drug effects

Substances

  • Antiviral Agents
  • 5'-noraristeromycin
  • Hydrolases
  • Adenosylhomocysteinase
  • Adenosine