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

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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
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