Citation: Le Pan, Xiu-Zhuang Li, Di-An Sun, Hui Jin, Hong-Ru Guo, Bo Qin. Design and synthesis of novel coumarin analogs and their nematicidal activity against five phytonematodes[J]. Chinese Chemical Letters, ;2016, 27(03): 375-379. doi: 10.1016/j.cclet.2016.01.029 shu

Design and synthesis of novel coumarin analogs and their nematicidal activity against five phytonematodes

Le Pan ^a,b ,
Xiu-Zhuang Li ^a ,
Di-An Sun ^c ,
Hui Jin ^a ,
Hong-Ru Guo ^a ,
Bo Qin ^a,,

a.
a. Key Laboratory of Chemistry of Northwestern Plant Resources of CAS and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China;
b.
b. University of Chinese Academy of Sciences, Beijing 100049, China;
c.
c. Institute of Medical Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, China

Corresponding author: Bo Qin,
Received Date: 26 June 2015
Available Online: 15 November 2015

The presence of hydroxyl groups at the C4 and C7 positions in coumarin backbone has been proposed as a potential modification site for providing excellent bioactivity according to previous studies. A series of novel coumarin derivatives were rationally designed and synthesized by use of a complex catalytic system for a targeted modification at the above sites. These derivatives were assayed for nematicidal activity. As predicted, the derivatization enhanced the activity of the coumarins against five nematodes. Compounds 7b, 9a, 10c and 11c showed significant strong nematicidal broad spectrum activity against all tested nematodes. Compound 10c was the most effective with the lowest LC₅₀ values against Meloidogyne incognita (5.1 μmol/L), Ditylenchus destructor (3.7 μmol/L), Bursaphelenchus mucronatus (6.4 μmol/L), Bursaphelenchus B. xylophilus (2.5 μmol/L) and Aphelenchoides besseyi (3.1 μmol/L), respectively. A brief investigation on the structure-activity relationships (SAR) revealed that the targeted modification by a C7 hydroxyl was optimum compared with that of a C4 hydroxyl and that the coupling chain length was crucial for the nematicidal activity.
- Coumarin analogs,
- Targeted design,
- Synthesis,
- Nematicidal activity,
- Structure-activity relationships
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