Photosynthesis-Inhibiting Activity of 1-[(2-Chlorophenyl)carbamoyl]- and 1-[(2-Nitrophenyl)carbamoyl]naphthalen-2-yl Alkylcarbamates

Molecules. 2017 Jul 17;22(7):1199. doi: 10.3390/molecules22071199.

Abstract

Eight 1-[(2-chlorophenyl)carbamoyl]naphthalen-2-yl alkylcarbamates and eight 1-[(2-nitrophenyl)carbamoyl]naphthalen-2-yl alkylcarbamates were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The PET-inhibiting activity of the compounds was relatively low; the corresponding IC50 values ranged from 0.05 to 0.664 mmol/L; and the highest activity within the series of compounds was observed for 1-[(2-chlorophenyl)-carbamoyl]naphthalen-2-yl propylcarbamate. It has been proven that the compounds are PET-inhibitors in photosystem II. Despite rather low PET-inhibiting activities, primary structure-activity trends can be discussed.

Keywords: PET inhibition; alkylcarbamates; hydroxynaphthalene-carboxamides; spinach chloroplasts; structure-activity relationships.

MeSH terms

  • Carbamates / chemistry
  • Carbamates / pharmacology*
  • Chloroplasts / drug effects
  • Chloroplasts / metabolism
  • Electron Transport / drug effects*
  • Inhibitory Concentration 50
  • Photosynthesis / drug effects*
  • Spinacia oleracea / metabolism
  • Structure-Activity Relationship

Substances

  • Carbamates