Discovery of 8-hydroxyadenines as a novel type of interferon inducer

J Med Chem. 2002 Dec 5;45(25):5419-22. doi: 10.1021/jm0203581.

Abstract

9-Benzyl-8-hydroxyadenine (6) was found to possess interferon-inducing activity in vitro as a lead compound. Although replacement of the 9-benzyl group of 6 did not improve the activity, the introduction of a substituent such as alkyl, alkylthio, alkylamino, and alkoxy groups into the 2-position of the adenine ring resulted in a remarkable increase in the activity. The 2-alkylthio (30-32), 2-butylamino (41), and 2-butoxy (47) analogues indicated the highest activities by oral administration to mice.

MeSH terms

  • Adenine / analogs & derivatives*
  • Adenine / chemical synthesis*
  • Adenine / pharmacology
  • Administration, Oral
  • Animals
  • In Vitro Techniques
  • Interferon Inducers / chemical synthesis*
  • Interferon Inducers / pharmacology
  • Mice
  • Spleen / cytology
  • Structure-Activity Relationship

Substances

  • Interferon Inducers
  • Adenine