Tetrahydroquinolinyl phosphinamidates and phosphonamidates enhancing tolerance towards drought stress in crops via interaction with ABA receptor proteins
New phosphorous-containing lead structures against drought stress in crops interacting with RCAR/(PYR/PYL) receptor proteins were identified starting from in-depth SAR studies of related sulfonamide lead structures and protein docking studies. A converging 6-step synthesis via phosphinic chlorides and phosphono chloridates as key intermediates afforded envisaged tetrahydroquinolinyl phosphinamidates and phosphonamidates. Whilst tetrahydroquinolinyl phosphonamidates 13a,b exhibited low to moderate target affinities, the corresponding tetrahydroquinolinyl phosphinamidates 12a,b revealed confirmed strong affinities for RCAR/ (PYR/PYL) receptor proteins in Arabidopsis thaliana on the same level as essential plant hormone abscisic acid (ABA) combined with promising efficacy against drought stress in vivo (broad-acre crops wheat and canola).
Decker, Luka J. B.,Dittgen, Jan,Frackenpohl, Jens,Freigang, J?rg,Génix, Pierre,Helmke, Hendrik,Lange, Gudrun,Luemmen, Peter,Schmidt, Jana,Schmutzler, Dirk,Vors, Jean-Pierre
Photolysis of 4-Methoxyphenyl Aryl Alkylphosphonates
UV irradiation of bis(4-methoxyphenyl) methylphosphonate 1a in methanol gave 4,4'-dimethoxybiphenyl 2a as the main product through an intramolecular excimer.With 4-cyanophenyl-4-methoxyphenyl methylphosphonate 1b 4-cyano-4'-methoxybiphenyl 2c and 4-cyano-2-(4'-methoxyphenyl)phenyl methylphosphonate 4b were obtained through an intramolecular exciplex. 3-Cyanophenyl-4-methoxyphenyl methyl phosphonate 1c gave only 3-cyano-4'-methoxybiphenyl 2f.Methyl 4-methoxyphenyl 4-chlorobenzylphosphonate 5a gave dimethyl 4-chlorobenzyl 2-(4'-methoxyphenyl)phosphonate and dimethyl 2-(4'-methoxyphenyl)benzylphosphonate.