Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 27, Issue 24, Pages 5457-5462Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2017.10.065
Keywords
1,2,4-Triazole thione; Mannich base; Ketol-acid reductoisomerase inhibitors; Fungicidal activity; Structure-activity relationship
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Funding
- National Natural Science Foundation of China [21372133]
- Zhejiang Province National Natural Science Foundation of China [LY16C140007]
- National Key Research and Development Program of China [2017YFD0200505]
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A series of new 3-substitutedphenyl-4-substitutedbenzylideneamino-1,2,4-triazole Mannich bases and bis-Mannich bases were synthesized through Mannich reaction with high yields. Their structures were confirmed by means of IR, H-1 NMR, C-13 NMR and elemental analysis. The preliminary bioassay indicated that compounds 7g, 7h and 7l exhibited potent in vitro inhibitory activities against ketol-acid reductoisomerase (KARI) with Ki value of (0.38 +/- 0.25), (6.59 +/- 2.75) and (8.46 +/- 3.99) mu mol/L, respectively, and were comparable with IpOHA. They could be new KARI inhibitors for follow-up research. Some of the title compounds also exhibited obvious herbicidal activities against Echinochloa crusgalli and remarkable in vitro fungicidal activities against Physalospora piricola and Rhizoctonia cerealis. The SAR of the compounds were analyzed, in which the molecular docking revealed the binding mode of 7g with the KARI, and the 3D-QSAR results provided useful information for guiding further optimization of this kind of structures to discover new fungicidal agents towards Rhizoctonia cerealis. (C) 2017 Elsevier Ltd. All rights reserved.
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