9-[(Hydroxymethyl)phenyl]adenines: new aryladenine substrates of adenosine deaminase

Bioorg Med Chem Lett. 2002 Jun 3;12(11):1489-92. doi: 10.1016/s0960-894x(02)00192-0.

Abstract

New phenyl adenine compounds 5-7 were synthesized as analogues of adenosine and studied for their adenosine deaminase (ADA) substrate activity. The 9-[(o-hydroxymethyl)phenyl]methyl]adenine 5 and 9-[(m-hydroxymethyl)phenyl]adenine 7 were deaminated by ADA, and 9-[(o-hydroxyethyl)phenyl]adenine 6 was not deaminated up to 7 days. The ADA substrates 5 and 7 were deaminated quantitatively to their inosine analogues in 10 and 6h, respectively.

Publication types

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

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemical synthesis
  • Adenosine / metabolism
  • Adenosine Deaminase / metabolism*
  • Animals
  • Cattle
  • Chromatography, Thin Layer
  • Deamination / drug effects
  • Inosine / analogs & derivatives
  • Inosine / metabolism
  • Intestines / enzymology
  • Magnetic Resonance Spectroscopy
  • Purines / metabolism
  • Spectrophotometry, Ultraviolet

Substances

  • Purines
  • Inosine
  • Adenosine Deaminase
  • Adenosine
  • purine