3'-deoxyribofuranose derivatives of 1-deaza and 3-deaza-adenosine and their activity as adenosine deaminase inhibitors

Nucleosides Nucleotides Nucleic Acids. 2001 Apr-Jul;20(4-7):1037-41. doi: 10.1081/NCN-100002486.

Abstract

2,6-Dichloro-1-deazapurine and 2,6-dichloro-3-deazapurine were coupled with 1,2-O-diacetyl-5-O-benzoyl-3-deoxy-beta-D-ribofuranose. Deprotection of the obtained compounds and reaction with liquid ammonia gave the desired 2-chloroadenine nucleosides, which were dechlorinated to afford the corresponding 1-deaza and 3-deazaadenosine derivatives. Biological studies performed on ADA from calf intestine showed that these new nucleosides are inhibitors of the enzyme.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / pharmacology
  • Adenosine Deaminase Inhibitors*
  • Animals
  • Cattle
  • Deoxyribose / analogs & derivatives*
  • Deoxyribose / chemistry
  • Deoxyribose / pharmacology
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Intestines / enzymology
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Spectrophotometry, Ultraviolet

Substances

  • Adenosine Deaminase Inhibitors
  • Enzyme Inhibitors
  • Deoxyribose
  • Adenosine