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
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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.
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-
[1]
[1] N.G. Ntalli, P. Caboni, Botanical nematicides:a review, J. Agric. Food. Chem. 60(2012) 9929-9940.
-
[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] 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] 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] (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] D.J. Chitwood, S.L.F. Meyer, Phytochemically based nematode control:opportunities and challenges, J. Nematol. 46(2014), 145-145.
-
[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] 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] D.J. Chitwood, Phytochemical based strategies for nematode control, Annu. Rev. Phytopathol. 40(2002) 221.
-
[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] 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] 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] 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] 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] 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] 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] M. Kawase, H. Sakagami, K. Hashimoto, et al., Structure-cytotoxic activity relationships of simple hydroxylated coumarins, Anticancer. Res. 23(2003) 3243-3246.
-
[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] 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] 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] 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] 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] 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.
-
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