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
1. [1]
  [1] N.G. Ntalli, P. Caboni, Botanical nematicides:a review, J. Agric. Food. Chem. 60(2012) 9929-9940.
2. [2]
  [2] J.T. Pechacek, T.M. Bargar, M.R. Sabol, (Ⅰ)nhibition of nematode induced root damage by derivatives of methylenecyclopropane acetic acid, Bioorg. Med. Chem. Lett. 7(1997) 2665-2668.
3. [3]
  [3] D.J. Chitwood, Research on plant-parasitic nematode biology conducted by the United States Department of Agriculture-Agricultural Research Service, Pest. Manag. Sci. 59(2003) 748-753.
4. [4]
  [4] T.C. Thoden, M. Boppré, J. Hallmann, Effects of pyrrolizidine alkaloids on the performance of plant-parasitic and free-living nematodes, Pest. Manag. Sci. 65(2009) 823-830.
5. [5]
  [5] (Ⅰ).O. Giannakou, (Ⅰ).A. Anastasiadis, S.R. Gowen, et al., Effects of a non-chemical nematicide combined with soil solarization for the control of root-knot nematodes, Crop. Prot. 26(2007) 1644-1654.
6. [6]
  [6] D.J. Chitwood, S.L.F. Meyer, Phytochemically based nematode control:opportunities and challenges, J. Nematol. 46(2014), 145-145.
7. [7]
  [7] J. Kearn, E. Ludlow, J. Dillon, et al., Fluensulfone is a nematicide with a mode of action distinct from anticholinesterases and macrocyclic lactones, Pestic. Biochem. Phys. 109(2014) 44-57.
8. [8]
  [8] S.M. Seo, J. Kim, S.H. Koh, et al., Nematicidal activity of natural ester compounds and their analogues against pine wood nematode, Bursaphelenchus xylophilus, J. Agr. Food. Chem. 62(2014) 9103-9108.
9. [9]
  [9] D.J. Chitwood, Phytochemical based strategies for nematode control, Annu. Rev. Phytopathol. 40(2002) 221.
10. [10]
  [10] M.E. Riveiro,N.De Kimpe, A. Moglioni, et al., Coumarins:old compounds with novel promising therapeutic perspectives, Curr. Med. Chem. 17(2010) 1325-1338.
11. [11]
  [11] B.R. Vijay Avin, P. Thirusangu, V. Lakshmi Ranganatha, et al., Synthesis and tumor inhibitory activity of novel coumarin analogs targeting angiogenesis and apoptosis, Eur. J. Med. Chem. 75(2014) 211-221.
12. [12]
  [12] M.E. Riveiro, D. Maes, R. Vázquez, et al., Coumarins:old compounds with novel promising therapeutic perspectives, Bioorg. Med. Chem. 17(2009) 6547-6559.
13. [13]
  [13] H. Cui, H. Jin, Q. Liu, et al., Nematicidal metabolites from roots of Stellera chamaejasme against Bursaphelenchus xylophilus and Bursaphelenchus mucronatus, Pest. Manag. Sci. 70(2014) 827-835.
14. [14]
  [14] Z. Yang, Z. Yu, L. Lei, et al., Nematicidal effect of volatiles produced by Trichoderma sp, J. Asia-Pac. Entomol. 15(2012) 647-650.
15. [15]
  [15] K. Takaishi, M. (Ⅰ)zumi, N. Baba, et al., Synthesis and biological evaluation of alkoxycoumarins as novel nematicidal constituents, Bioorg. Med. Chem. Lett. 18(2008) 5614-5617.
16. [16]
  [16] S. Lee, K. Sivakumar, W.S. Shin, et al., Synthesis and anti-angiogenesis activity of coumarin derivatives, Bioorg. Med. Chem. Lett. 16(2006) 4596-4599.
17. [17]
  [17] M. Kawase, H. Sakagami, K. Hashimoto, et al., Structure-cytotoxic activity relationships of simple hydroxylated coumarins, Anticancer. Res. 23(2003) 3243-3246.
18. [18]
  [18] M. Adfa, Y. Hattori, T. Yoshimura, et al., Antitermite activity of 7-alkoxycoumarins and related analogs against Coptotermes formosanus Shiraki, (Ⅰ)nt. Biodeterior. Biodegrad. 74(2012) 129-135.
19. [19]
  [19] Y. Chen, S.L. Wang, X.Q. Xu, et al., Synthesis and biological investigation of coumarin piperazine (piperidine) derivatives as potential multireceptor atypical antipsychotics, J. Med. Chem. 56(2013) 4671-4690.
20. [20]
  [20] N. Priya, A. Gupta, K. Chand, et al., Characterization of 4-methyl-2-oxo-1, 2-dihydroquinolin-6-yl acetate as an effective antiplatelet agent, Bioorg. Med. Chem. Lett. 18(2010) 4085-4094.
21. [21]
  [21] Q.L. Dang, W.K. Kim, C.M. Nguyen, et al., Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens, J. Agr. Food. Chem. 59(2011) 11160-11167.
22. [22]
  [22] P. Caboni, L. Tronci, B. Liori, et al., Tulipaline A:structure-activity aspects as a nematicide and V-ATPase inhibitor, Pestic. Biochem. Phys. 112(2014) 33-39.
23. [23]
  [23] J.O. Kong, S.M. Lee, Y.S. Moon, et al., Nematicidal activity of plant essential oils against Bursaphelenchus xylophilus (Nematoda:Aphelenchoididae), J. Asia-Pac. Entomol. 9(2006) 173-178.
1. [1]
  Wei Sun , Anjing Liao , Li Lei , Xu Tang , Ya Wang , Jian Wu . Research progress on piperidine-containing compounds as agrochemicals. Chinese Chemical Letters, 2025, 36(1): 109855-. doi: 10.1016/j.cclet.2024.109855
2. [2]
  Ali Dai , Zhiguo Zheng , Liusheng Duan , Jian Wu , Weiming Tan . Small molecule chemical scaffolds in plant growth regulators for the development of agrochemicals. Chinese Chemical Letters, 2025, 36(4): 110462-. doi: 10.1016/j.cclet.2024.110462
3. [3]
  Shaobo Wang , Honggui Yang , Chunni Zhao , Deyu Hu , Baoan Song . Antibacterial agrochemicals: Recent research progress and outlook. Chinese Chemical Letters, 2026, 37(1): 111543-. doi: 10.1016/j.cclet.2025.111543
4. [4]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
5. [5]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
6. [6]
  Jian Song , Shenghui Wang , Qiuge Liu , Xiao Wang , Shuo Yuan , Hongmin Liu , Saiyang Zhang . N-Benzyl arylamide derivatives as novel and potent tubulin polymerization inhibitors against gastric cancers: Design, structure–activity relationships and biological evaluations. Chinese Chemical Letters, 2025, 36(2): 109678-. doi: 10.1016/j.cclet.2024.109678
7. [7]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
8. [8]
  Xinzhe ZHANG , Jiarong XU , Mochou GAO , Yage LIU , Yanbao ZHAO , Jingzeng CUI , Xueyan ZOU . Silver chloride/chitosan-based chloramine nanohybrid with excellent antibacterial activity: Design and structure characterization as well as Ag⁺-Cl^- synergistic antibacterial effect. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 428-438. doi: 10.11862/CJIC.20250123
9. [9]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
10. [10]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
11. [11]
  Ying Chen , Ronghua Yan , Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066
12. [12]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
13. [13]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
14. [14]
  Wen-Rui Li , Ru-Bing Wang , Huiqiang Wang , Jin-Yao Yong , Yu-Huan Li , Shi-Shan Yu , Shuang-Gang Ma . Ring-reorganization strategy for asymmetric synthesis of sesquiterpenoid illihenin A and its antiviral activity evaluation. Chinese Chemical Letters, 2025, 36(11): 110945-. doi: 10.1016/j.cclet.2025.110945
15. [15]
  Tiantian Zhang , Hanbo Liu , Junbiao Chang , Yonggang Meng . Total synthesis of ADPr-ATP and evaluation of the antiviral activity of pRib-AMP prodrug. Chinese Chemical Letters, 2026, 37(2): 111380-. doi: 10.1016/j.cclet.2025.111380
16. [16]
  Chengyu JIANG , Xufeng LIU . Synthesis, structural characterization, electrocatalytic proton reduction, and fungicidal activity of thiazole-containing di-iron complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 355-364. doi: 10.11862/CJIC.20250253
17. [17]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
18. [18]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
19. [19]
  Xiaomeng Hu , Jie Yu , Lijie Sun , Linfeng Zhang , Wei Zhou , Dongpeng Yan , Xinrui Wang . Synthesis of an AVB@ZnTi-LDH composite with synergistically enhance UV blocking activity and high stability for potential application in sunscreen formulations. Chinese Chemical Letters, 2024, 35(11): 109466-. doi: 10.1016/j.cclet.2023.109466
20. [20]
  Bofei JIA , Zhihao LIU , Zongyuan GAO , Shuai ZHOU , Mengxiang WU , Qian ZHANG , Xiamei ZHANG , Shuzhong CHEN , Xiaohan YANG , Yahong LI . Cu(Ⅱ) and Cu(Ⅰ) complexes based on derivatives of imidazo[1,5-a]pyridine: Synthesis, structures, in situ metal-ligand reactions, and catalytic activity. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 1020-1036. doi: 10.11862/CJIC.20240317

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1520)
HTML views(57)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142