Synthesis of new nebularine analogues and their inhibitory activity against adenosine deaminase

Chem Pharm Bull (Tokyo). 2015;63(2):134-42. doi: 10.1248/cpb.c14-00731.

Abstract

A number of new 2,6-disubstituted-1-deazanebularine analogues as well as two structurally related pyrazole-fused tricyclic nucleosides were prepared. Their synthesis was carried out by the conversion of 6-amino-2-picoline to a suitable 1-deazapurine, followed by a Vorbrüggen type glycosylation and subsequent elaboration of the condensed pyrazole ring. The synthesized nebularine analogues proved to be weak adenosine deaminase inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Deaminase / chemistry*
  • Adenosine Deaminase / metabolism
  • Adenosine Deaminase Inhibitors / chemical synthesis*
  • Adenosine Deaminase Inhibitors / chemistry
  • Adenosine Deaminase Inhibitors / metabolism
  • Animals
  • Cattle
  • Glycosylation
  • Magnetic Resonance Spectroscopy
  • Protein Binding
  • Purine Nucleosides / chemical synthesis
  • Purine Nucleosides / chemistry*
  • Purine Nucleosides / metabolism
  • Pyrazoles / chemistry
  • Ribonucleosides / chemical synthesis
  • Ribonucleosides / chemistry*
  • Ribonucleosides / metabolism

Substances

  • Adenosine Deaminase Inhibitors
  • Purine Nucleosides
  • Pyrazoles
  • Ribonucleosides
  • pyrazole
  • nebularine
  • Adenosine Deaminase