Citation: Sun Haiyang, Li Hui, Wang Jiayi, Song Gonghua. Synthesis and nematicidal activity of piperazinedione derivatives based on the natural product Barettin[J]. Chinese Chemical Letters, ;2018, 29(6): 977-980. doi: 10.1016/j.cclet.2017.10.015 shu

Synthesis and nematicidal activity of piperazinedione derivatives based on the natural product Barettin

Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

Corresponding author: Song Gonghua, ghsong@ecust.edu.cn
Received Date: 18 June 2017
Revised Date: 3 October 2017
Accepted Date: 12 October 2017
Available Online: 14 June 2017

Figures(2)

Nematodes are serious constraints of crop production worldwide. However, the traditional nematicides suffer from the side-effects, including environmental and human toxicity. Herein, more than 70 novel piperazinedione derivatives based on the natural product Barettin were synthesized and evaluated against the root-knot nematode Meloidogyne incognita (M. incognita). While most of synthesized compounds exhibited certain nematicidal activity at high concentration, the best one showed a nematicidal activity of 75% at 2.4 μmol/L.
- 5-HT,
- Barettin,
- Nature product,
- Nematicidal activity,
- Piperazinedione derivatives
1. [1]
  H.J. Atkinson, C.J. Lilley, P.E. Urwin, Curr. Opin. Biotechnol. 23(2012) 251-256. doi: 10.1016/j.copbio.2011.09.004
2. [2]
  J.T. Jones, A. Haegeman, E.G. Danchin, et al., Mol. Plant Pathol. 14(2013) 946-961. doi: 10.1111/mpp.2013.14.issue-9
3. [3]
  W.P. Porter, J.W. Jaeger, I.H. Carlson, Toxicol. Ind. Health 15(1999) 133-150. doi: 10.1177/074823379901500111
4. [4]
  C. Ragoucy-Sengler, A. Tracqui, A. Chavonnet, et al., Hum. Exp. Toxicol. 19(2000) 657-662. doi: 10.1191/096032700672133218
5. [5]
  G. Wang, X. Chen, Y. Chang, et al., Chin. Chem. Lett. 26(2015) 1502-1506. doi: 10.1016/j.cclet.2015.10.024
6. [6]
  H.C. Meher, V.T. Gajbhiye, G. Chawla, et al., Pest Manag. Sci. 65(2009) 1201-1207. doi: 10.1002/ps.v65:11
7. [7]
  N.G. Ntalli, P. Caboni, J. Agric. Food Chem. 60(2012) 9929-9940. doi: 10.1021/jf303107j
8. [8]
  B.B. Toure, D.G. Hall, Chem. Rev. 109(2009) 4439-4486. doi: 10.1021/cr800296p
9. [9]
  Y. Zhang, Y. Feng, Z. Li, et al., Chin. Chem. Lett. 28(2017) 1228-1231. doi: 10.1016/j.cclet.2017.04.003
10. [10]
  Q. Hou, Y. Jing, X. Shao, Chin. Chem. Lett. 28(2017) 1723-1726. doi: 10.1016/j.cclet.2017.05.016
11. [11]
  Y. Asahi, T. Yoshida, Chem. Pharm. Bull. 25(1977) 2211-2216. doi: 10.1248/cpb.25.2211
12. [12]
  S. Valcic, G.A. Wächter, C.M. Eppler, et al., J. Nat. Prod. 65(2002) 1270-1273. doi: 10.1021/np020068n
13. [13]
  S. Begum, A. Wahab, B.S. Siddiqui, et al., J. Nat. Prod. 63(2000) 765-767. doi: 10.1021/np9903548
14. [14]
  E. Hedner, M. Sjögren, P.A. Frändberg, et al., J. Nat. Prod. 69(2006) 1421-1424. doi: 10.1021/np0601760
15. [15]
  D.E. Nichols, C.D. Nichols, Chem. Rev. 108(2008) 1614-1641. doi: 10.1021/cr078224o
16. [16]
  S.C. Leiser, Y. Li, A.L. Pehrson, et al., ACS Chem. Neurosci. 6(2015) 970-986. doi: 10.1021/cn500340j
17. [17]
  S. Srinivasan, L. Sadegh, I.C. Elle, et al., Cell Metab. 7(2008) 533-544. doi: 10.1016/j.cmet.2008.04.012
18. [18]
  S.A. Heusser, Ö. Yoluk G. Klement, et al, J. Neurochem. 138(2016) 243-253. doi: 10.1111/jnc.2016.138.issue-2
19. [19]
  E.R. Sawin, R. Ranganathan, H.R. Horvitz, Neuron 26(2000) 619-631. doi: 10.1016/S0896-6273(00)81199-X
20. [20]
  T. Shea-Donohue, R. Sun, J.A. Bohl, et al., Cytokine 75(2015) 62-67. doi: 10.1016/j.cyto.2015.06.007
21. [21]
  S. C. Trowell S. Saubern C. Liao, Patent, US 20050054680, 2005.
22. [22]
  M. Cai, Z. Li, Q. Huang, et al., Chem. Biodivers. 5(2008) 1844-1855. doi: 10.1002/cbdv.200890172
23. [23]
  M. Cai, Z. Li, F. Fan, et al., J. Agric. Food Chem. 58(2010) 2624-2629. doi: 10.1021/jf902640u
24. [24]
  Y. Shen, J. Wang, G. Song, Mol. Divers. 18(2013) 195-202.
25. [25]
  A. Johnson, J. Bergman, M. Sjögren, et al., Tetrahedron 60(2004) 961-965. doi: 10.1016/j.tet.2003.11.031
26. [26]
  S. Peng, M., Zhao, Y. Wang, et al., Patent, CN201410260127, (2014).
27. [27]
  C. Howes, N.W. Alcock, B.T. Golding, et al., J. Chem. Soc. Perkin Trans. 1(1983) 2229-2287.
28. [28]
  J. Huang, A. Chen, H. Zhang, et al., Appl. Environ. Microbiol. 81(2015) 5326-5334. doi: 10.1128/AEM.01025-15
1. [1]
  Guo-Ping Yin , Ya-Juan Li , Li Zhang , Ling-Gao Zeng , Xue-Mei Liu , Chang-Hua Hu . Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9. Chinese Chemical Letters, 2024, 35(8): 109035-. doi: 10.1016/j.cclet.2023.109035
2. [2]
  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
3. [3]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
4. [4]
  Peng Chen , Lijuan Liang , Yufei Zhu , Zhimin Xing , Zhenhua Jia , Teck-Peng Loh . Strategies for constructing seven-membered rings: Applications in natural product synthesis. Chinese Chemical Letters, 2024, 35(6): 109229-. doi: 10.1016/j.cclet.2023.109229
5. [5]
  Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
6. [6]
  Fangwen Peng , Zhen Luo , Yingjin Ma , Haibo Ma . Theoretical study of aromaticity reversal in dimethyldihydropyrene derivatives. Chinese Journal of Structural Chemistry, 2024, 43(5): 100273-100273. doi: 10.1016/j.cjsc.2024.100273
7. [7]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
8. [8]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
9. [9]
  Yadan SUN , Xinfeng LI , Qiang LIU , Oshio Hiroki , Yinshan MENG . Structures and magnetism of dinuclear Co complexes based on imine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2212-2220. doi: 10.11862/CJIC.20240131
10. [10]
  Zhuwen Wei , Jiayan Chen , Congzhen Xie , Yang Chen , Shifa Zhu . Divergent de novo construction of α-functionalized pyrrole derivatives via coarctate reaction. Chinese Chemical Letters, 2024, 35(12): 109677-. doi: 10.1016/j.cclet.2024.109677
11. [11]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
12. [12]
  Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
13. [13]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
14. [14]
  Shuying Li , Weiwei ZhuGe , Xuan Sun , Chongzhen Sun , Zhaojun Liu , Chenghe Xiong , Min Xiao , Guofeng Gu . Convergent synthesis and immunological study of oligosaccharide derivatives related to galactomannan from Antrodia cinnamomea. Chinese Chemical Letters, 2024, 35(5): 109089-. doi: 10.1016/j.cclet.2023.109089
15. [15]
  Tao Wei , Jiahao Lu , Pan Zhang , Qi Zhang , Guang Yang , Ruizhi Yang , Daifen Chen , Qian Wang , Yongfu Tang . An intermittent lithium deposition model based on bimetallic MOFs derivatives for dendrite-free lithium anode with ultrahigh areal capacity. Chinese Chemical Letters, 2024, 35(8): 109122-. doi: 10.1016/j.cclet.2023.109122
16. [16]
  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
17. [17]
  Jun-Ming Cao , Kai-Yang Zhang , Jia-Lin Yang , Zhen-Yi Gu , Xing-Long Wu . Differential bonding behaviors of sodium/potassium-ion storage in sawdust waste carbon derivatives. Chinese Chemical Letters, 2024, 35(4): 109304-. doi: 10.1016/j.cclet.2023.109304
18. [18]
  Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
19. [19]
  Liping Zhao , Xixi Guo , Zhimeng Zhang , Xi Lu , Qingxuan Zeng , Tianyun Fan , Xintong Zhang , Fenbei Chen , Mengyi Xu , Min Yuan , Zhenjun Li , Jiandong Jiang , Jing Pang , Xuefu You , Yanxiang Wang , Danqing Song . Novel berberine derivatives as adjuvants in the battle against Acinetobacter baumannii: A promising strategy for combating multi-drug resistance. Chinese Chemical Letters, 2024, 35(10): 109506-. doi: 10.1016/j.cclet.2024.109506
20. [20]
  Yu Hong , Yuqian Jiang , Chenhuan Yuan , Decai Wang , Yimeng Sun , Jian Jiang . Unraveling temperature-dependent supramolecular polymorphism of naphthalimide-substituted benzene-1,3,5-tricarboxamide derivatives. Chinese Chemical Letters, 2024, 35(12): 109909-. doi: 10.1016/j.cclet.2024.109909

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(663)
HTML views(41)

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