Adenosine deaminase inhibitors. Synthesis and biological evaluation of C1' and nor-C1' derivatives of (+)-erythro-9-(2(S)-hydroxy-3(R)-nonyl)adenine

J Med Chem. 1992 Oct 30;35(22):4180-4. doi: 10.1021/jm00100a025.


The synthesis of various chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine, (+)-EHNA, from (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol by condensation with 5-amino-4,6-dichloropyrimidine is described. The compounds synthesized were C1'- and nor-C1'-(+)-EHNA derivatives. When tested with calf spleen ADA, C1'-OH- and nor-C1'-(+)-EHNA had comparable inhibitory activity that was 1 order of magnitude lower than that of (+)-EHNA. Potency was reduced further in nor-C1' derivatives.

Publication types

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

MeSH terms

  • Adenine / analogs & derivatives*
  • Adenine / chemical synthesis
  • Adenine / metabolism
  • Adenine / pharmacology
  • Adenosine Deaminase / metabolism
  • Adenosine Deaminase Inhibitors*
  • Animals
  • Binding Sites
  • Cattle
  • In Vitro Techniques
  • Stereoisomerism
  • Structure-Activity Relationship


  • Adenosine Deaminase Inhibitors
  • 9-(2-hydroxy-3-nonyl)adenine
  • Adenosine Deaminase
  • Adenine