Synthesis and Nematicidal Activities of 8-Azabicyclo[3.2.1]-octane-3-isoxazole Oxime Derivatives

doi:10.6023/cjoc201601036

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (4): 760-767.DOI: 10.6023/cjoc201601036 Previous Articles Next Articles

ARTICLE

8-氮杂双环[3.2.1]辛烷-3-异噁唑肟类衍生物的合成及其杀线虫活性

陆青, 沈巧英, 孙璐, 王佳毅, 宋恭华

华东理工大学药学院上海市化学生物学重点实验室上海 200237

收稿日期:2016-01-17 修回日期:2016-02-29 发布日期:2016-03-11
通讯作者: 宋恭华 E-mail:ghsong@ecust.edu.cn
基金资助:
国家自然科学基金(No.21572060)资助项目.

Synthesis and Nematicidal Activities of 8-Azabicyclo[3.2.1]-octane-3-isoxazole Oxime Derivatives

Lu Qing, Shen Qiaoying, Sun Lu, Wang Jiayi, Song Gonghua

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

Received:2016-01-17 Revised:2016-02-29 Published:2016-03-11
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21572060).

1. Synthesis and Nematicidal Activities of 8-Azabicyclo[3.2.1]-octane-3-isoxazole Oxime Derivatives.PDF(7410KB)

Abstract

Based on the potential nematicidal activities of tropane derivatives structure, 19 unreported 8-azabicyclo[3.2.1]- octane-3-isoxazole oxime derivatives were designed and synthesized by 1,3-dipolar cycloaddition reaction. Their structures were confirmed by ¹H NMR, ¹³C NMR and HRMS techniques. Preliminary bioassay results showed that targeted compounds exhibited good nematicidal activities against Meloidogyne incognita at concentration of 25 mg/L, and 8-methyl-8-azabicyclo- [3.2.1]octan-3-one-O-((3-(4-nitrophenyl)-4,5-dihydroisoxazol-5-yl)methyl)oxime (9e) showed the best nematicidal activities with 55.6% at concentration of 1 mg/L.

Key words: 8-azabicyclo, nematicide, serotonin, 1,3-dipolar cycloaddition reaction

Cite this article

Lu Qing, Shen Qiaoying, Sun Lu, Wang Jiayi, Song Gonghua. Synthesis and Nematicidal Activities of 8-Azabicyclo[3.2.1]-octane-3-isoxazole Oxime Derivatives[J]. Chin. J. Org. Chem., 2016, 36(4): 760-767.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Atkinson, H. J.; Lilley, C. J.; Urwin, P. E. Curr. Opin. Biotechnol. 2012, 23, 251.
[2] Arnot, L. F.; Veale, D. J. H.; Steyl, J. C. A.; Myburgh, J. G. J. S. Afr. Vet. Assoc. 2011, 82, 232.
[3] Souza, A. D.; Narvencar, K. P. S.; Sindhoora, K. V. J. Neurol. Sci. 2013, 335, 36.
[4] Qin, S. J.; Gan, J. Y.; Liu, W. P.; Becker, J. O. J. Agric. Food Chem. 2004, 52, 6239.
[5] Sánchez-Moreno, S.; Alonso-Prados, E.; Alonso-Prados, J. L.; García-Baudín, J. M. Pest Manage. Sci. 2009, 65, 82.
[6] Pitterna, T.; Cassayre, J.; Hüter, O. F.; Jung, P. M. J.; Maienfisch, P.; Kessabi, F. M.; Quaranta, L.; Tobler, H. Bioorg. Med. Chem. 2009, 17, 4085.
[7] Kearn, J.; Ludlow, E.; Dillon, J.; O'Connor, V.; Holden-Dye, L. Pestic. Biochem. Phys. 2014, 109, 44.
[8] Mushtaq, M.; Feely, W. F.; Syintsakos, L. R.; Wislocki, P. G, J. Agric. Food Chem. 1996, 44, 940
[9] Liu, Q. S.; Ma, X. G.; Shen, B. Y. New Cen. Agrochem. 2014, 4, 54 (in Chinese). (刘钦胜, 马新刚, 申宝玉, 今日农化, 2014, 4, 54.)
[10] Tierney, A. J. Comp. Biochem. Physiol., Part A: Mol. Integr. Physiol. 2001, 128, 791.
[11] Nassel, D. R. Prog. Neurobiol. 1996, 48, 325.
[12] Nassel, D. R. Prog. Neurobiol. 1988, 30, 1.
[13] Osborne, R. H. Pharmacol. Ther. 1996, 69, 117.
[14] Lange, A. B. Arch. Insect Biochem. Physiol. 2004, 56, 179.
[15] Cai, M. Y.; Li, Z.; Fan, F.; Huang, Q. C.; Shao, X. S.; Song, G. H. J. Agric. Food Chem. 2009, 58, 2624.
[16] Shen, Y.; Wang, J. Y.; Song, G. H. Mol. Diversity 2014, 18, 195.
[17] Trowell, S. C.; Saubern, S.; Liao, C. Y. US 20050054680, 2005 [Chem. Abstr. 2003, 138, 200330].
[18] Trowell, S. C.; Dumancic, M.; Liao, C. Y. Easr, P. US 20030186370, 2003 [Chem. Abstr. 2001, 135, 191974].
[19] Thompson, A. J.; Lummis, S. C. Curr. Pharm. Des. 2006, 12, 3615.
[20] Hibert, M. F.; Hoffmann, R.; Miller, R. C.; Carr, A. A. J. Med. Chem. 1990, 33, 1594.
[21] Swain, C. J.; Baker, R.; Kneen, C.; Moseley, J.; Saunders, J.; Seward, E. M.; Stevenson, G.; Beer, M.; Stanton, J.; Watling, K. J. Med. Chem. 1991, 34, 140.
[22] Song, B. A.; Liu, X. H.; Yang, S.; Hu, D. Y.; Jin, L. H.; Zhang, Y. T. Chin. J. Org. Chem. 2005, 25, 507 (in Chinese). (宋宝安, 刘新华, 杨松, 胡德禹, 金林红, 张玉涛, 有机化学 2005, 25, 507.)
[23] He, H. W.; Li, M. Q.; Huang, G. L. Pesticides 2000, 8, 4 (in Chinese). (贺红武, 李美强, 黄刚良, 农药, 2000, 8, 4.)
[24] Mihara, J.; Murata, T.; Yamazaki, D.; Yoneta, Y.; Shibuya, K.; Shimojo, E.; Görgens, U. WO 2008019760, 2008 [Chem. Abstr. 2008, 148, 262594].
[25] Li, M. Q.; He, H. W. Chem. Reag. 2001, 23, 271 (in Chinese). (李美强, 贺红武, 化学试剂, 2001, 23, 271.)
[26] Lu, T. J.; Tzeng, G. M. J. Chin. Chem. Soc. 2000, 47, 189.
[27] Koyama, J.; Sugita, T.; Suzuta, Y.; Irie, H. Chem. Pharm. Bull. 1983, 31, 2601.
[28] Kleinschmidt, R. F.; Cope, A. C. J. Am. Chem. Soc. 1944, 66, 1929.

8-氮杂双环[3.2.1]辛烷-3-异噁唑肟类衍生物的合成及其杀线虫活性

Synthesis and Nematicidal Activities of 8-Azabicyclo[3.2.1]-octane-3-isoxazole Oxime Derivatives

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 2

Recommended Articles

Metrics

Comments

[1]	Qingbo Xu, Peibo Liang, Huizhe Lu, Shuhui Jin, Yanhong Dong, Jianjun Zhang. Design, Synthesis and Bioactivity of Fluopyram Derivatives Containing Diamide Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3116-3125.
[2]	Li Wan, Hu Aixi, Liu Ailin, Peng Junmei, Xia Lin, Tan Weiqing. Synthesis and Biological Activities of 4-Alkyl-6-aryl-1,3-thiazines [J]. Chin. J. Org. Chem., 2013, 33(07): 1478-1482.