Synthesis and nematocide activity of S-glycopyranosyl-6,7-diarylthiolumazines

Bioorg Med Chem. 2004 Aug 15;12(16):4431-7. doi: 10.1016/j.bmc.2004.06.004.

Abstract

6,7-Diaryl derivatives of mono and di-S-glycopyranosylthiolumazine derivatives 5-8 were prepared to test their nematocide activity. In vitro tests against Caenorhabditis elegans were performed and it was found that monosubstituted derivatives 5-7 showed higher activity than the corresponding unsubstituted 2-thiolumazines 1-3, whilst 2-S,4-S-di-glycopyranosylpteridine derivative 8 was inactive in contrast to unsubstituted derivative 4. In order to check whether the lack of activity of 8 was due to the two bulky substituents of the pteridine nucleus, 2-S,4-S-dimethyl derivative 9 was synthesized and assayed showing also lack of activity. A theoretical study on the stability of the different possible tautomers of compound 4 was carried out in an attempt to explain some, in appearance, anomalous (13)C NMR data of this compound.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antinematodal Agents / chemical synthesis*
  • Antinematodal Agents / pharmacology*
  • Caenorhabditis elegans / drug effects
  • Glycosides / chemical synthesis*
  • Glycosides / pharmacology*
  • Pteridines / chemical synthesis*
  • Pteridines / pharmacology*

Substances

  • Antinematodal Agents
  • Glycosides
  • Pteridines