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

Authors :: Frackenpohl J
Decker LJB
Dittgen J
Freigang J
Génix P
Helmke H
Lange G
Luemmen P
Schmidt J
Schmutzler D
Vors JP
Source :: Bioorganic & medicinal chemistry [Bioorg Med Chem] 2020 Nov 15; Vol. 28 (22), pp. 115725. Date of Electronic Publication: 2020 Aug 30.
Publication Year :: 2020
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).<br /> (Copyright © 2020 Elsevier Ltd. All rights reserved.)

Subjects :: Abscisic Acid metabolism
Amides chemistry
Arabidopsis drug effects
Arabidopsis metabolism
Crops, Agricultural metabolism
Crystallography, X-Ray
Dose-Response Relationship, Drug
Molecular Docking Simulation
Molecular Structure
Organophosphorus Compounds chemistry
Plant Proteins metabolism
Quinolines chemistry
Structure-Activity Relationship
Amides pharmacology
Crops, Agricultural drug effects
Droughts
Organophosphorus Compounds pharmacology
Plant Proteins chemistry
Quinolines pharmacology

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