Synthesis and insecticidal activities of 1, 8-naphthyridine derivatives
- Corresponding author: Shao Xu-Sheng, shaoxusheng@ecust.edu.cn
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
Wang K., Qian X., Cui J.. ChemInform abstract:design, synthesis, and bioactivity of cyanonitrovinyl neonicotinoids as potential insecticides[J]. Cheminform, 2011,42:1117-1122.
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
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
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.
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
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
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
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
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
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.
Nishigaki S., Mizushima N., Yoneda F.. Synthetic antibacterials. 3. Nitrofurylvinyl-18-naphthyridine derivatives[J]. J. Med. Chem., 1971,14:638-640.
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.
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.
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
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
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.
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
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
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
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
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
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
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
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
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
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
Tang H., Ji P.. Using the statistical program r instead of spss to analyze data[J]. ACS Symp. Ser., 2015,1166:135-151.
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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