Tetrahydroquinolinyl phosphinamidates and phosphonamidates enhancing tolerance towards drought stress in crops via interaction with ABA receptor proteins |
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| Institution: | 1. Research & Development, Weed Control - Bayer AG, CropScience Division, Industriepark Höchst, D-65926 Frankfurt am Main;2. Research & Development, Disease Control - Bayer S.A.S., Crop Science Division, CRLD, 14 Impasse Pierre Baizet, 69263 Lyon, France;3. Research & Development, Research Technology, Bayer AG, CropScience Division, Gebäude 6240, Alfred-Nobel-Straße 50, 40789 Monheim, Germany;1. Ribeirão Preto Medical School, University of São Paulo, Ribeirão Preto, São Paulo, Brazil;2. Regional Blood Center of Ribeirão Preto, Ribeirão Preto, São Paulo, Brazil;3. Federal University of São Paulo, São Paulo, São Paulo, Brazil;4. Department of Microbiology, Biomedical Sciences Institute, University of São Paulo, São Paulo, São Paulo, Brazil;5. Protein Signaling and Interactions (GIGA), University of Liège, Liège, Belgium;6. Gonçalo Moniz Research Center (CPqGM), Oswaldo Cruz Foundation (FIOCRUZ), Salvador, Bahia, Brazil;7. School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Ribeirão Preto, São Paulo, Brazil;8. Institute of Tropical Medicine of São Paulo, University of São Paulo, São Paulo, São Paulo, Brazil;9. Molecular and Cellular Epigenetics (GIGA), University of Liège, Liège, Belgium;1. School of Computer and Electronics Information, Guangxi University, Nanning 530004, China;2. College of Electrical Engineering, Guangxi University, Nanning 530004, China;1. Structural Bioinformatics Lab, CSIR-Institute of Himalayan Bioresource Technology (CSIR-IHBT), Palampur, HP 176061, India;2. Biotechnology division, CSIR-IHBT, Palampur, HP 176061, India;3. Academy of Scientific & Innovative Research (AcSIR), Ghaziabad, 201002, India |
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| 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). |
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| Keywords: | Phytochemistry Drought stress Phosphinamidates Phosphonamidates Abscisic acid receptor proteins |
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