Citation: Hou Qing-Qing, Jing Yi-Fei, Shao Xu-Sheng. Synthesis and insecticidal activities of 1, 8-naphthyridine derivatives[J]. Chinese Chemical Letters, ;2017, 28(8): 1723-1726. doi: 10.1016/j.cclet.2017.05.016 shu

Synthesis and insecticidal activities of 1, 8-naphthyridine derivatives

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

Corresponding author: Shao Xu-Sheng, shaoxusheng@ecust.edu.cn
Received Date: 28 February 2017
Revised Date: 1 April 2017
Accepted Date: 15 May 2017
Available Online: 17 August 2017

Figures(2)

1, 8-Naphthyridines (NAP) are biological important scaffolds in bioactive molecules design. By hybrid of NAP with neonicotinoid core structure, nine novel NAP derivatives were synthesized and subjected to insecticidal activities evaluation. Some of the compounds showed excellent insecticidal activity against cowpea aphids (Aphis craccivora) with LC₅₀ values ranging from 0.011 mmol/L to 0.067 mmol/L. The results indicated that 1, 8-naphthyridine can be used as insecticidal structure for further modification.
- 1, 8-Naphthyridine,
- Insecticide ativity,
- Neonicotinoid,
- Aphid
1. [1]
  Wang K., Qian X., Cui J.. ChemInform abstract:design, synthesis, and bioactivity of cyanonitrovinyl neonicotinoids as potential insecticides[J]. Cheminform, 2011,42:1117-1122.
2. [2]
  Furlan L., Kreutzweiser D.. Alternatives to neonicotinoid insecticides for pest control:case studies in agriculture and forestry[J]. Environ. Sci. Pollut. Res., 2015,22:135-147. doi: 10.1007/s11356-014-3628-7
3. [3]
  Nauen R., Denholm I.. Resistance of insect pests to neonicotinoid insecticides:Current status and future prospects[J]. Arch. Insect Biochem. Physiol., 2005,58:200-215. doi: 10.1002/(ISSN)1520-6327
4. [4]
  Liu X., Wu X., Long Z.. Photodegradation of imidacloprid in aqueous solution by metal-free catalyst graphitic carbon nitride using an energy-saving lamp[J]. J. Agri. Food. Chem., 2015,19:4754-4760.
5. [5]
  Li Z., Shao X., Sun F., Zhu F.. One-Pot, Three-component synthesis of 1, 8-naphthyridine derivatives from heterocyclic ketene aminals, malononitrile dimer, and aryl aldehydes[J]. Synlett, 2015,26:2306-2312. doi: 10.1055/s-00000083
6. [6]
  Fu L., Feng X., Wang J.J.. Efficient synthesis and evaluation of antitumor activities of novel functionalized 18-naphthyridine derivatives[J]. Acs. Comb. Sci., 2015,17:24-31. doi: 10.1021/co500120b
7. [7]
  Jeanneau E., Nicolle -, Benoit M., Guyod -, Namil A., Leclerc G.. New thiazolo[32-a] pyrimidine derivatives, synthesis and structure-activity relationships[J]. Eur. J. Med. Chem., 1992,27:115-120. doi: 10.1016/0223-5234(92)90099-M
8. [8]
  Tsuzuki Y., Tomita K., Shibamori K.. Synthesis and structure-activity relationships of novel 7-substituted 14-dihydro-4-oxo-1-(2-thiazolyl)-1. 8-naphthyridine-3-carboxylic acids as antitumor agents. Part 2[J]. J. Med. Chem., 2002,45:5564-5575. doi: 10.1021/jm010057b
9. [9]
  Yang L., Wang S., Sun D.. Development of a biomimetic chondroitin sulfate-modified hydrogel to enhance the metastasis of tumor cells[J]. Sci. Rep., 2016,6:1-13. doi: 10.1038/s41598-016-0001-8
10. [10]
  Santilli A.A., Scotese A.C., Yurchenco J.A.. ChemInform Abstract:synthesis and antibacteial evaluation of 1, 2, 3, -tetrahydro-4-oxo-1, 8-naphthridine-3-carboxylic acid esters, carbonitriles, and carboxamides[J]. J. Med. Chem., 1976,7:1038-1041.
11. [11]
  Nishigaki S., Mizushima N., Yoneda F.. Synthetic antibacterials. 3. Nitrofurylvinyl-18-naphthyridine derivatives[J]. J. Med. Chem., 1971,14:638-640.
12. [12]
  Singh S.B., Kaelin D.E., Meinke P.T.. Structure activity relationship of C-2 ether substituted 15-naphthyridine analogs of oxabicyclooctane-linked novel bacterial topoisomerase inhibitors as broad-spectrum antibacterial agents (Part-5)[J]. Bioorg. Med. Chem. Lett., 2015,17:3630-3635.
13. [13]
  Gao L.Z., Xie Y.S., Li T., Huang W.L., Hu G.Q.. Synthesis and antibacterial activity of novel[12, 4]triazolo[3, 4-h] [1, 8]naphthyridine-7-carboxylic acid derivatives[J]. Chin. Chem. Lett., 2014,26:149-151.
14. [14]
  Li B., Harjani J.R., Cormier N.S.. Besting vitamin E:Sidechain substitution is key to the reactivity of naphthyridinol antioxidants in lipid bilayers[J]. J. Am. Chem. Soc., 2013,135:1394-1405. doi: 10.1021/ja309153x
15. [15]
  Kuroda T., Suzuki F., Tamura T., Ohmori K., Hosoe H.. A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-18-naphthyridine-3-carboxamides[J]. J. Med. Chem., 1992,35:1130-1136. doi: 10.1021/jm00084a019
16. [16]
  S. Bekkering, B.A. Blok, L.A. Joosten, et al., In vitro experimental model of trained innate immunity in human primary monocytes, Clin. Vaccine Immunol. 12(23(12)) (2016) 349-16.
17. [17]
  Manera C., Malfitano A.M., Parkkari T., Lucchesi V., Carpi S.. New quinolone-and 1, 8-naphthyridine-3-carboxamides as selective CB2 receptor agonists with anticancer and immuno modulatory activity[J]. Eur. J. Med. Chem., 2015,97:10-18. doi: 10.1016/j.ejmech.2015.04.034
18. [18]
  Nam T.G., Rector C.L., Kim H.Y.. Tetrahydro-18-naphthyridinol analogues of alpha-tocopherol as antioxidants in lipid membranes and low-density lipoproteins[J]. J. Am. Chem. Soc., 2007,129:10211-10219. doi: 10.1021/ja072371m
19. [19]
  Barreiro E.J., Camara C.A., Verli H.. Design, synthesis, and pharmacological profile of novel fused pyrazolo[4, 3-d]pyridine and pyrazolo[3, 4-b] [1, 8]naphthyridine isosteres:a new class of potent and selective acetylcholinesterase inhibitors[J]. J. Med. Chem., 2003,46:1144-1152. doi: 10.1021/jm020391n
20. [20]
  De L.R.C., Egea J., Marco-Contelles J.. Synthesis, inhibitory activity of cholinesterases, and neuroprotective profile of novel 1, 8-naphthyridine derivatives[J]. J. Med. Chem., 2010,53:5129-5143. doi: 10.1021/jm901902w
21. [21]
  You Q., Li Z., Huang C.. Discovery of a novel series of quinolone and naphthyridine derivatives as potential topoisomerase i inhibitors by scaffold modification[J]. J. Med. Chem., 2009,52:5649-5661. doi: 10.1021/jm900469e
22. [22]
  Dhar A.K., Mahesh R., Jindal A., Devadoss T., Bhatt S.. Design, synthesis, and pharmacological evaluation of novel 2-(4-substituted piperazin-1-yl)1, 8 naphthyridine 3-carboxylic acids as 5-ht 3 receptor antagonists for the management of depression[J]. Chem. Biol. Drug Des., 2014,84:721-731. doi: 10.1111/cbdd.12370
23. [23]
  Laura Betti P.L.F., Tiziana C., Gino G.. study on affinity profile toward native human and bovine adenosine receptors of a series of 18-naphthyridine derivatives[J]. J. Med. Chem., 2004,47:3019-3031. doi: 10.1021/jm030977p
24. [24]
  Hartner F.W., Hsiao Y., Eng K.K.. Methods for the synthesis of 5, 6, 7, 8-tetrahydro-1, 8-naphthyridine fragments for avb3 integrin antagonists[J]. J. Org. Chem., 2004,69:8723-8730. doi: 10.1021/jo0486950
25. [25]
  Ferrarini P.L., Mori C., Manera C.. A novel class of highly potent and selective A1 adenosine antagonists:structure-affinity profile of a series of 18-naphthyridine derivatives[J]. J. Med. Chem., 2000,43:2814-2823. doi: 10.1021/jm990321p
26. [26]
  Mohan M., Gujar G.T.. Local variation in susceptibility of the diamondback moth, Plutella xylostella (Linnaeus) to insecticides and role of detoxification enzymes[J]. Crop Prot., 2003,22:495-504. doi: 10.1016/S0261-2194(02)00201-6
27. [27]
  Tang H., Ji P.. Using the statistical program r instead of spss to analyze data[J]. ACS Symp. Ser., 2015,1166:135-151.
28. [28]
  Chae S.H., Kim S.I., Yeon S.H., Lee S.W., Ahn Y.J.. Adulticidal activity of phthalides identified in cnidium officinale rhizome to b-and q-biotypes of bemisia tabaci[J]. J. Agric. Food. Chem., 2011,59:8193-8198. doi: 10.1021/jf201927t
1. [1]
  Zhi Wang , Lingpeng Yan , Yelin Hao , Jingxia Zheng , Yongzhen Yang , Xuguang Liu . Highly efficient and photothermally stable CDs@ZIF-8 for laser illumination. Chinese Chemical Letters, 2024, 35(10): 109430-. doi: 10.1016/j.cclet.2023.109430
2. [2]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
3. [3]
  Xin Zhang , Junyu Chen , Xiang Pei , Linxin Yang , Liang Wang , Luona Chen , Guangmei Yang , Xibo Pei , Qianbing Wan , Jian Wang . Drug-loading ZIF-8 for modification of microporous bone scaffold to promote vascularized bone regeneration. Chinese Chemical Letters, 2024, 35(6): 108889-. doi: 10.1016/j.cclet.2023.108889
4. [4]
  Si-Hua Liu , Jun-Hao Zhou , Jian-Ke Sun . Interconnecting zero-dimensional porous organic cages into sub-8 nm nanofilm for bio-inspired separation. Chinese Journal of Structural Chemistry, 2024, 43(7): 100312-100312. doi: 10.1016/j.cjsc.2024.100312
5. [5]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
6. [6]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
7. [7]
  Zhiwei Chen , Heyun Sheng , Xue Li , Menghan Chen , Xin Li , Qiuling Song . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives. Chinese Chemical Letters, 2024, 35(4): 108937-. doi: 10.1016/j.cclet.2023.108937
8. [8]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
9. [9]
  Xuexia Lin , Yihui Zhou , Jiafu Hong , Xiaofeng Wei , Bin Liu , Chong-Chen Wang . Facile preparation of ZIF-8/ZIF-67-derived biomass carbon composites for highly efficient electromagnetic wave absorption. Chinese Chemical Letters, 2024, 35(9): 109835-. doi: 10.1016/j.cclet.2024.109835
10. [10]
  Jianqiu Li , Yi Zhang , Songen Liu , Jie Niu , Rong Zhang , Yong Chen , Yu Liu . Cucurbit[8]uril-based non-covalent heterodimer realized NIR cell imaging through topological transformation from nanowire to nanorod. Chinese Chemical Letters, 2024, 35(10): 109645-. doi: 10.1016/j.cclet.2024.109645
11. [11]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
12. [12]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
13. [13]
  Shuo Li , Xinran Liu , Yongjie Zheng , Jun Ma , Shijie You , Heshan Zheng . Effective peroxydisulfate activation by CQDs-MnFe₂O₄@ZIF-8 catalyst for complementary degradation of bisphenol A by free radicals and non-radical pathways. Chinese Chemical Letters, 2024, 35(5): 108971-. doi: 10.1016/j.cclet.2023.108971
14. [14]
  Ya-Nan Yang , Zi-Sheng Li , Sourav Mondal , Lei Qiao , Cui-Cui Wang , Wen-Juan Tian , Zhong-Ming Sun , John E. McGrady . Metal-metal bonds in Zintl clusters: Synthesis, structure and bonding in [Fe₂Sn₄Bi₈]^3– and [Cr₂Sb₁₂]^3–. Chinese Chemical Letters, 2024, 35(8): 109048-. doi: 10.1016/j.cclet.2023.109048
15. [15]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
16. [16]
  Liang MA , Honghua ZHANG , Weilu ZHENG , Aoqi YOU , Zhiyong OUYANG , Junjiang CAO . Construction of highly ordered ZIF-8/Au nanocomposite structure arrays and application of surface-enhanced Raman spectroscopy. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1743-1754. doi: 10.11862/CJIC.20240075
17. [17]
  Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H₂O₂ Production and Cr(VI) Reduction over a Hierarchical Ti₃C₂/In₄SnS₈ Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
18. [18]
  Jiayu Huang , Kuan Chang , Qi Liu , Yameng Xie , Zhijia Song , Zhiping Zheng , Qin Kuang . Fe-N-C nanostick derived from 1D Fe-ZIFs for Electrocatalytic oxygen reduction. Chinese Journal of Structural Chemistry, 2023, 42(10): 100097-100097. doi: 10.1016/j.cjsc.2023.100097
19. [19]
  Jun Xiong , Ke-Ke Chen , Neng-Bin Xie , Wei Chen , Wen-Xuan Shao , Tong-Tong Ji , Si-Yu Yu , Yu-Qi Feng , Bi-Feng Yuan . Demethylase-assisted site-specific detection of N¹-methyladenosine in RNA. Chinese Chemical Letters, 2024, 35(5): 108953-. doi: 10.1016/j.cclet.2023.108953
20. [20]
  Ling-Hao Zhao , Hai-Wei Yan , Jian-Shuang Jiang , Xu Zhang , Xiang Yuan , Ya-Nan Yang , Pei-Cheng Zhang . Effective assignment of positional isomers in dimeric shikonin and its analogs by ¹H NMR spectroscopy. Chinese Chemical Letters, 2024, 35(5): 108863-. doi: 10.1016/j.cclet.2023.108863

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(557)
HTML views(2)

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