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Tetrahydroquinolinyl phosphinamidates and phosphonamidates enhancing tolerance towards drought stress in crops via interaction with ABA receptor proteins.

Authors
  • Frackenpohl, Jens1
  • Decker, Luka J B2
  • Dittgen, Jan2
  • Freigang, Jörg3
  • Génix, Pierre4
  • Helmke, Hendrik2
  • Lange, Gudrun2
  • Luemmen, Peter2
  • Schmidt, Jana2
  • Schmutzler, Dirk2
  • Vors, Jean-Pierre4
  • 1 Research & Development, Weed Control - Bayer AG, CropScience Division, Industriepark Höchst, D-65926 Frankfurt am Main. Electronic address: [email protected]
  • 2 Research & Development, Weed Control - Bayer AG, CropScience Division, Industriepark Höchst, D-65926 Frankfurt am Main.
  • 3 Research & Development, Research Technology, Bayer AG, CropScience Division, Gebäude 6240, Alfred-Nobel-Straße 50, 40789 Monheim, Germany. , (Germany)
  • 4 Research & Development, Disease Control - Bayer S.A.S., Crop Science Division, CRLD, 14 Impasse Pierre Baizet, 69263 Lyon, France. , (France)
Type
Published Article
Journal
Bioorganic & medicinal chemistry
Publication Date
Nov 15, 2020
Volume
28
Issue
22
Pages
115725–115725
Identifiers
DOI: 10.1016/j.bmc.2020.115725
PMID: 33007548
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

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). Copyright © 2020 Elsevier Ltd. All rights reserved.

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