Synthesis and biological evaluation of nonsymmetrical aromatic disulfides as novel inhibitors of acetohydroxyacid synthase

Bioorg Med Chem Lett. 2013 Jul 1;23(13):3723-7. doi: 10.1016/j.bmcl.2013.05.013. Epub 2013 May 16.

Abstract

46 Novel nonsymmetrical aromatic disulfides containing [1,3,4]thiadiazole or [1,3,4]oxadiazole groups were synthesized and their biological activities were evaluated as inhibitors of acetohydroxyacid synthase (AHAS, EC 2.2.1.6). Besides their strong in vitro inhibition against plant AHAS, compounds 3e and 3f also display 80-100% post-emergence herbicidal activities in greenhouse bioassay at 1500g /ha dosage. The assay of exogenous branched-chain amino acids supplementation on rape root growth of 3e suggests that the herbicidal activity has relationship with AHAS inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetolactate Synthase / antagonists & inhibitors*
  • Acetolactate Synthase / metabolism
  • Arabidopsis / enzymology
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Hydrocarbons, Aromatic / chemical synthesis
  • Hydrocarbons, Aromatic / chemistry
  • Hydrocarbons, Aromatic / pharmacology*
  • Molecular Structure
  • Oxadiazoles / chemistry
  • Structure-Activity Relationship
  • Sulfides / chemical synthesis
  • Sulfides / chemistry
  • Sulfides / pharmacology*
  • Thiadiazoles / chemistry

Substances

  • Enzyme Inhibitors
  • Hydrocarbons, Aromatic
  • Oxadiazoles
  • Sulfides
  • Thiadiazoles
  • Acetolactate Synthase