Photochemical transformation of a cellulose biosynthesis inhibitor into phytoene desaturase inhibitors

Bioorg Med Chem Lett. 2021 Oct 15:50:128317. doi: 10.1016/j.bmcl.2021.128317. Epub 2021 Aug 13.

Abstract

Mode of action studies showed that 5-methyl-N,N-bis[6-(trifluoromethyl)pyridin-3-yl]pyridin-2-amine (4), a representative from a new class of herbicidal tris-pyridyl amines, is an inhibitor of cellulose biosynthesis (CB). The compound undergoes an oxidative photocyclization, when exposed to UV-B light (300-340 nm) in the presence of oxygen, to give a new class of herbicidal pyrrolodipyridines. These compounds are potent inhibitors of the herbicide target enzyme phytoene desaturase and no longer inhibit CB.

Keywords: Cellulose biosynthesis; Herbicide; Hytoene desaturase; Photocyclization; Tris-pyridylamines.

MeSH terms

  • Brassicaceae
  • Cells, Cultured
  • Cellulose / biosynthesis*
  • Drug Design
  • Herbicides / chemistry
  • Herbicides / pharmacology*
  • Molecular Structure
  • Nicotiana / drug effects
  • Nicotiana / metabolism
  • Oxidoreductases / antagonists & inhibitors*
  • Photochemical Processes*
  • Pyridazines
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacology
  • Ultraviolet Rays

Substances

  • Herbicides
  • Pyridazines
  • Pyridines
  • Cellulose
  • Oxidoreductases
  • phytoene dehydrogenase
  • norflurazone