4.5 Article

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

Journal

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 23, Issue 13, Pages 3723-3727

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2013.05.013

Keywords

Nonsymmetrical aromatic disulfides; Acetohydroxyacid synthase; Branched-chain amino acids; Enzyme inhibition; Herbicidal activity

Funding

  1. Natural Science Foundation of China [21272128]
  2. National Basic Research Project of China [2010CB126103]
  3. National Key Technology Research and Development Program [2011BAE06B05-3]

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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 1500 g/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. (C) 2013 Elsevier Ltd. All rights reserved.

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