Synthesis and bioactivity of novel pyrazole oxime derivatives containing oxazole ring

注册 English

Synthesis and bioactivity of novel pyrazole oxime derivatives containing oxazole ring

Sen-Lin Wang , Yu-Jun Shi , Hai-Bing He , Yu Li , Yang Li , Hong Dai

Citation: Sen-Lin Wang, Yu-Jun Shi, Hai-Bing He, Yu Li, Yang Li, Hong Dai. Synthesis and bioactivity of novel pyrazole oxime derivatives containing oxazole ring[J]. Chinese Chemical Letters, 2015, 26(6): 672-674. doi: 10.1016/j.cclet.2015.04.017 shu

shu

Synthesis and bioactivity of novel pyrazole oxime derivatives containing oxazole ring

Sen-Lin Wang ^a, ,
Yu-Jun Shi ^{a,b,
,} ,
Hai-Bing He ^b, ,
Yu Li ^b, ,
Yang Li ^a, ,
Hong Dai ^{b,
,}

通讯作者: Yu-Jun Shi,
Hong Dai,

基金项目:
This study was funded by the National Natural Science Foundation of China (No. 21202089) (No. 21202089)

the Research Foundation of the Six People Peak of Jiangsu Province (Nos. 2011-SWYY-009, 2013-SWYY-013) (Nos. 2011-SWYY-009, 2013-SWYY-013)

the Technology Project Fund of Nantong City (Nos. AS2013004, CP12013002). (Nos. AS2013004, CP12013002)

摘要: A series of novel pyrazole oxime derivatives containing oxazole ring were designed and synthesized. The title compounds were structurally confirmed by ¹H NMR, ¹³C NMR spectra and elemental analyses. Preliminary bioassay results showed that some of the title compounds displayed promising fungicidal activity besides insecticidal and acaricidal activity. Particularly, compound 8c exhibited potent fungicidal activity against cucumber Pseudoperonospora cubensis beyond good insecticidal activity against Aphis craccivora and Nilaparvata lugens.

关键词:

English

Synthesis and bioactivity of novel pyrazole oxime derivatives containing oxazole ring

Sen-Lin Wang ^a, ,
Yu-Jun Shi ^{a,b,
,} ,
Hai-Bing He ^b, ,
Yu Li ^b, ,
Yang Li ^a, ,
Hong Dai ^{b,
,}

1.
a School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, China;
2.
b College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, China

Corresponding author: Yu-Jun Shi, Hong Dai,

Received Date: 27 February 2015
Available Online: 23 April 2015
Fund Project:

Abstract: A series of novel pyrazole oxime derivatives containing oxazole ring were designed and synthesized. The title compounds were structurally confirmed by ¹H NMR, ¹³C NMR spectra and elemental analyses. Preliminary bioassay results showed that some of the title compounds displayed promising fungicidal activity besides insecticidal and acaricidal activity. Particularly, compound 8c exhibited potent fungicidal activity against cucumber Pseudoperonospora cubensis beyond good insecticidal activity against Aphis craccivora and Nilaparvata lugens.

Key words:

1. [1] H.S. Chen, Z.M. Li, Y.F. Han, Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl (alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (thiadiazoles), J. Agric. Food Chem. 48 (2000) 5312-5315.[1] H.S. Chen, Z.M. Li, Y.F. Han, Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl (alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (thiadiazoles), J. Agric. Food Chem. 48 (2000) 5312-5315.
2. [2] H. Dai, Y.Q. Li, D. Du, et al., Synthesis and biological activities of novel pyrazole oxime derivatives containing a 2-chloro-5-thiazolyl moiety, J. Agric. Food Chem. 56 (2008) 10805-10810.[2] H. Dai, Y.Q. Li, D. Du, et al., Synthesis and biological activities of novel pyrazole oxime derivatives containing a 2-chloro-5-thiazolyl moiety, J. Agric. Food Chem. 56 (2008) 10805-10810.
3. [3] H.J. Song, Y.X. Liu, L.X. Xiong, et al., Design, synthesis, and insecticidal evaluation of new pyrazole derivatives containing imine, oxime ether, and dihydroisoxazoline groups based on the inhibitor binding pocket of respiratory complex I, J. Agric. Food Chem. 61 (2013) 8730-8736.[3] H.J. Song, Y.X. Liu, L.X. Xiong, et al., Design, synthesis, and insecticidal evaluation of new pyrazole derivatives containing imine, oxime ether, and dihydroisoxazoline groups based on the inhibitor binding pocket of respiratory complex I, J. Agric. Food Chem. 61 (2013) 8730-8736.
4. [4] H. Dai, Y.S. Xiao, Z. Li, et al., The thiazoylmethoxy modification on pyrazole oximes: synthesis and insecticidal biological evaluation beyond acaricidal activity, Chin. Chem. Lett. 25 (2014) 1014-1016.[4] H. Dai, Y.S. Xiao, Z. Li, et al., The thiazoylmethoxy modification on pyrazole oximes: synthesis and insecticidal biological evaluation beyond acaricidal activity, Chin. Chem. Lett. 25 (2014) 1014-1016.
5. [5] H.J. Ma, Y.H. Li, Q.F. Zhao, et al., Synthesis and herbicidal activity of novel N-(2,2,2)-trifluoroethylpyrazole derivatives, J. Agric. Food Chem. 58 (2010) 4356-4360.[5] H.J. Ma, Y.H. Li, Q.F. Zhao, et al., Synthesis and herbicidal activity of novel N-(2,2,2)-trifluoroethylpyrazole derivatives, J. Agric. Food Chem. 58 (2010) 4356-4360.
6. [6] S. Mert, R. Kasimogullari, T. Ica, et al., Synthesis, structure-activity relationships, and in vitro antibacterial and antifungal activity evaluations of novel pyrazole carboxylic and dicarboxylic acid derivatives, Eur. J. Med. Chem. 78 (2014) 86-96.[6] S. Mert, R. Kasimogullari, T. Ica, et al., Synthesis, structure-activity relationships, and in vitro antibacterial and antifungal activity evaluations of novel pyrazole carboxylic and dicarboxylic acid derivatives, Eur. J. Med. Chem. 78 (2014) 86-96.
7. [7] K.M. Dawood, T.M.A. Eldebss, H.S.A. El-Zahabi, et al., Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents, Eur. J. Med. Chem. 70 (2013) 740-749.[7] K.M. Dawood, T.M.A. Eldebss, H.S.A. El-Zahabi, et al., Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents, Eur. J. Med. Chem. 70 (2013) 740-749.
8. [8] M.B. Swanson, W.A. Ivancic, A.M. Saxena, et al., Direct photolysis of Fenpyroximate in a buffered aqueous solution under a xenon lamp, J. Agric. Food Chem. 43 (1995) 513-518.[8] M.B. Swanson, W.A. Ivancic, A.M. Saxena, et al., Direct photolysis of Fenpyroximate in a buffered aqueous solution under a xenon lamp, J. Agric. Food Chem. 43 (1995) 513-518.
9. [9] H. Hamaguchi, O. Kajihara, M. Katoh, Development of a new acaricide, Fenpyroximate, J. Pestic. Sci. 20 (1995) 173-175.[9] H. Hamaguchi, O. Kajihara, M. Katoh, Development of a new acaricide, Fenpyroximate, J. Pestic. Sci. 20 (1995) 173-175.
10. [10] K. Motoba, H. Nishizawa, T. Suzuki, et al., Species-specific detoxification metabolism of Fenpyroximate, a potent acaricide, Pestic. Biochem. Physiol. 67 (2000) 73-84.[10] K. Motoba, H. Nishizawa, T. Suzuki, et al., Species-specific detoxification metabolism of Fenpyroximate, a potent acaricide, Pestic. Biochem. Physiol. 67 (2000) 73-84.
11. [11] P. Guo, J.H. Huang, Q.C. Huang, et al., Synthesis of novel 1,3-oxazole derivatives with insect growth-inhibiting activities, Chin. Chem. Lett. 24 (2013) 957-961.[11] P. Guo, J.H. Huang, Q.C. Huang, et al., Synthesis of novel 1,3-oxazole derivatives with insect growth-inhibiting activities, Chin. Chem. Lett. 24 (2013) 957-961.
12. [12] G.Y. Li, X.H. Qian, J.N. Cui, et al., Synthesis and herbicidal activity of novel 3-aminocarbonyl-2-oxazolidinethione derivatives containing a substituted pyridine ring, J. Agric. Food Chem. 54 (2006) 125-129.[12] G.Y. Li, X.H. Qian, J.N. Cui, et al., Synthesis and herbicidal activity of novel 3-aminocarbonyl-2-oxazolidinethione derivatives containing a substituted pyridine ring, J. Agric. Food Chem. 54 (2006) 125-129.
13. [13] C.K. Ryu, R.Y. Lee, N.Y. Kim, et al., Synthesis and antifungal activity of benzo[-d]oxazole-4,7-diones, Bioorg. Med. Chem. Lett. 19 (2009) 5924-5926.[13] C.K. Ryu, R.Y. Lee, N.Y. Kim, et al., Synthesis and antifungal activity of benzo[-d]oxazole-4,7-diones, Bioorg. Med. Chem. Lett. 19 (2009) 5924-5926.
14. [14] A.V. Gadakh, C. Pandit, S.S. Rindhe, et al., Synthesis and antimicrobial activity of novel fluorine containing 4-(substituted-2-hydrobenzoyl)-1H-pyrazoles and pyrazolyl benzo[d]oxazoles, Bioorg. Med. Chem. Lett. 20 (2010) 5572-5576.[14] A.V. Gadakh, C. Pandit, S.S. Rindhe, et al., Synthesis and antimicrobial activity of novel fluorine containing 4-(substituted-2-hydrobenzoyl)-1H-pyrazoles and pyrazolyl benzo[d]oxazoles, Bioorg. Med. Chem. Lett. 20 (2010) 5572-5576.
15. [15] D. Sriram, P. Yogeeswari, R. Thirumurugan, et al., Discovery of new antitubercular oxazolyl thiosemicarbazones, J. Med. Chem. 49 (2006) 3448-3450.[15] D. Sriram, P. Yogeeswari, R. Thirumurugan, et al., Discovery of new antitubercular oxazolyl thiosemicarbazones, J. Med. Chem. 49 (2006) 3448-3450.
16. [16] Q.Q. Zhao, S.H. Liu, Y.H. Li, et al., Design, synthesis, and biological activities of novel 2-cyanoacrylates containing oxazole, oxadiazole, or quinoline moieties, J. Agric. Food Chem. 57 (2009) 2849-2855.[16] Q.Q. Zhao, S.H. Liu, Y.H. Li, et al., Design, synthesis, and biological activities of novel 2-cyanoacrylates containing oxazole, oxadiazole, or quinoline moieties, J. Agric. Food Chem. 57 (2009) 2849-2855.
17. [17] H.J. Park, K. Lee, S.J. Park, et al., Identification of antitumor activity of pyrazole oxime ethers, Bioorg. Med. Chem. Lett. 15 (2005) 3307-3312.[17] H.J. Park, K. Lee, S.J. Park, et al., Identification of antitumor activity of pyrazole oxime ethers, Bioorg. Med. Chem. Lett. 15 (2005) 3307-3312.
18. [18] H. Dai, Y.F. Zhao, P. Niu, et al., Synthesis and biological activity of 1-{4-[(2-cyanoimino-1,3-thiazolidine-3-yl)methyl] thiazol-2-yl}-3-aroyl ureas, Chin. J. Org. Chem. 33 (2013) 1568-1572.[18] H. Dai, Y.F. Zhao, P. Niu, et al., Synthesis and biological activity of 1-{4-[(2-cyanoimino-1,3-thiazolidine-3-yl)methyl] thiazol-2-yl}-3-aroyl ureas, Chin. J. Org. Chem. 33 (2013) 1568-1572.
19. [19] Y. Zhao, C.H. Mao, Y.Q. Li, et al., Synthesis, crystal structure, and insecticidal activity of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole, J. Agric. Food Chem. 56 (2008) 7326-7332.[19] Y. Zhao, C.H. Mao, Y.Q. Li, et al., Synthesis, crystal structure, and insecticidal activity of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole, J. Agric. Food Chem. 56 (2008) 7326-7332.
20. [20] X.S. Shao, H. Fu, X.Y. Xu, et al., Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: design, synthesis, crystal structure, and insecticidal activities, J. Agric. Food Chem. 58 (2010) 2696-2702.[20] X.S. Shao, H. Fu, X.Y. Xu, et al., Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: design, synthesis, crystal structure, and insecticidal activities, J. Agric. Food Chem. 58 (2010) 2696-2702.
21. [21] S. Tu, L.H. Xu, L.Y. Ye, et al., Synthesis and fungicidal activities of novel indenesubstituted oxime ether strobilurins, J. Agric. Food Chem. 56 (2008) 5247-5253.[21] S. Tu, L.H. Xu, L.Y. Ye, et al., Synthesis and fungicidal activities of novel indenesubstituted oxime ether strobilurins, J. Agric. Food Chem. 56 (2008) 5247-5253.

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