Synthesis and immunostimulatory activity of 8-substituted amino 9-benzyladenines as potent Toll-like receptor 7 agonists

Bioorg Med Chem Lett. 2006 Sep 1;16(17):4559-63. doi: 10.1016/j.bmcl.2006.06.017. Epub 2006 Jun 19.

Abstract

Several 9-benzyl adenine derivatives bearing various substituted amines at the 8-position have been prepared and evaluated for interferon induction in peripheral blood mononuclear cells (PBMC) from healthy human donors. The 8-bromoadenine derivative 5 was used as a versatile intermediate for all substitutions. The most active 8-substituted amino compound was found to be the 8-morpholinoethylamino derivative 19 which had an EC(50) in the submicromolar range.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Adenine / analogs & derivatives*
  • Adenine / chemical synthesis
  • Adenine / chemistry
  • Adenine / pharmacology
  • Amination
  • Humans
  • Leukocytes / drug effects
  • Molecular Structure
  • Structure-Activity Relationship
  • Toll-Like Receptor 7 / agonists*
  • Toll-Like Receptor 7 / immunology*

Substances

  • Toll-Like Receptor 7
  • 9-benzyladenine
  • Adenine