Synthesis and fungicidal activity study of novel daphneolone analogs with 2, 6-dimethylmorpholine

引用本文: Gao-Fei Xu, Xin-Ling Yang, Peng Lei, Xi-li Liu, Xue-Bo Zhang, Yun Ling. Synthesis and fungicidal activity study of novel daphneolone analogs with 2, 6-dimethylmorpholine[J]. Chinese Chemical Letters, 2016, 27(4): 555-558. shu

Citation: Gao-Fei Xu, Xin-Ling Yang, Peng Lei, Xi-li Liu, Xue-Bo Zhang, Yun Ling. Synthesis and fungicidal activity study of novel daphneolone analogs with 2, 6-dimethylmorpholine[J]. Chinese Chemical Letters, 2016, 27(4): 555-558. shu

Synthesis and fungicidal activity study of novel daphneolone analogs with 2, 6-dimethylmorpholine

a Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China;
b Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China
基金项目:
This work was financially supported by the National Natural Science Foundation of China (No. 21272266) and the National High Technology Research and Development Program of China (No. 2011AA10A202).

摘要: A series of novel daphneolone analogswas designed and synthesized on the basis of natural product 1, 5-diphenyl-2-penten-1-one (I) from Stellera chamaejasme L. as lead compound, whereby 2, 6-dimethylmorpholine moiety was introduced to replace 1-phenyl group. Their structures were confirmed by IR, ¹H NMR, and HRMS (ESI) or elemental analysis, ¹³C NMR for some representative compounds. The two isomers of target compounds were separated and identified by NOESY technique and chemical method. All of the synthesized compounds have been evaluated for anti-plant pathogenic fungi activities. The results showed that some compounds exhibited moderate to good antifungal activities against tested fungi at the concentration of 50 mg/L. Among them, compound 7d, with a 4-bromine-substituted phenyl group and cis-2, 6-dimethylmorpholine moiety, displayed best activity with an EC₅₀ of 23.87 μmol/L against Valsa mali, superior to lead compound I. In addition, preliminary structure-activity relationship analysis indicated that, between two isomers of target compounds, the antifungal activities of the isomer with cis-2, 6-dimethylmorpholine were better than the trans-isomer.

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English

Synthesis and fungicidal activity study of novel daphneolone analogs with 2, 6-dimethylmorpholine

a Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China;
b Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China
Received Date: 05 November 2015
Revised Date: 03 December 2015
Available Online: 02 February 2016
Fund Project:
This work was financially supported by the National Natural Science Foundation of China (No. 21272266) and the National High Technology Research and Development Program of China (No. 2011AA10A202).

Abstract: A series of novel daphneolone analogswas designed and synthesized on the basis of natural product 1, 5-diphenyl-2-penten-1-one (I) from Stellera chamaejasme L. as lead compound, whereby 2, 6-dimethylmorpholine moiety was introduced to replace 1-phenyl group. Their structures were confirmed by IR, ¹H NMR, and HRMS (ESI) or elemental analysis, ¹³C NMR for some representative compounds. The two isomers of target compounds were separated and identified by NOESY technique and chemical method. All of the synthesized compounds have been evaluated for anti-plant pathogenic fungi activities. The results showed that some compounds exhibited moderate to good antifungal activities against tested fungi at the concentration of 50 mg/L. Among them, compound 7d, with a 4-bromine-substituted phenyl group and cis-2, 6-dimethylmorpholine moiety, displayed best activity with an EC₅₀ of 23.87 μmol/L against Valsa mali, superior to lead compound I. In addition, preliminary structure-activity relationship analysis indicated that, between two isomers of target compounds, the antifungal activities of the isomer with cis-2, 6-dimethylmorpholine were better than the trans-isomer.

Key words:

1. [1] M. Farag, M.S. Mohammed, I. Foud, et al., The role of natural products in drug discovery and development, WJPR 4(2015) 22-33.
2. [2] D.J. Newman, G.M. Cragg, Natural products as sources of new drugs over the 30 years from 1981 to 2010, J. Nat. Prod. 75(2012) 311-335.
3. [3] P. Gao, T.P. Hou, R. Gao, Q. Cui, S.G. Liu, Activity of the botanical aphicides 1,5-diphenyl-1-pentanone and 1,5-diphenyl-2-penten-1-one on two species of Aphididae, Pest Manage. Sci. 57(2001) 307-310.
4. [4] T.P. Hou, Q. Cui, S.H. Chen, N.T. Hou, S.G. Liu, New compounds against aphides from Stellera chamaejasme L, Chin. J. Org. Chem. 22(2002) 67.
5. [5] P. Gao, Y.P. Liu, S.G. Liu, Effects of dp-B on ATPase activity of insect plasma membrane, Pestic. Biochem. Physiol. 80(2004) 157-162.
6. [6] T. Lu, L. Chen, T.P. Hou, et al., Synthesis and structure-activity study of botanical aphicides 1,5-diphenyl-1-pentanone analogues, Pestic. Biochem. Phys. 89(2007) 60-64.
7. [7] L. Chen, X.L. Wang, T. Lu, et al., Lead optimization and insecticidal activity of analogues of daphneolone isolated from Stellera chamaejasme L, Pest. Manage. Sci. 63(2007) 928-934.
8. [8] H. Jin, Y.C. Geng, Z.Y. Yu, et al., Lead optimization and anti-plant pathogenic fungi activities of daphneolone analogues from Stellera chamaejasme L, Pestic. Biochem. Phys. 93(2009) 133-137.
9. [9] S.X. Yang, Design, Synthesis and Bioactivity of Natural Product Daphneolone Analogues, China Agricultural University, Beijing, 2012, Ph.D. Dissertation.
10. [10] R.L. Xie, Structure Modification and Bioactivity of Natural Active Compound Daphneolone, China Agricultural University, Beijing, 2014, Ph.D. Dissertation.
11. [11] S.X. Yang, T.N. Kang, C.H. Rui, X.L. Yang, et al., Design, synthesis, and insecticidal activity of 1,5-diphenyl-1-pentanone analogues, Chin. J. Chem. 29(2011) 2394.
12. [12] R.L. Xie, Y. Song, X.L. Yang, et al., Synthesis and fungicidal activity of novel daphneolone analogues, Chem. J. Chin. Univ. 35(2014) 1451.
13. [13] C.M. Duarte, H. Verli, et al., New optimized piperamide analogues with potent in vivo hypotensive properties, Eur. J. Pharm. Sci. 23(2004) 363-369.
14. [14] N.C. Chen, Bioassay of Pesticides, Beijing Agricultural University Press, Beijing, 1991, pp. 161-162.

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Synthesis and fungicidal activity study of novel daphneolone analogs with 2, 6-dimethylmorpholine

English

Synthesis and fungicidal activity study of novel daphneolone analogs with 2, 6-dimethylmorpholine

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Synthesis and fungicidal activity study of novel daphneolone analogs with 2, 6-dimethylmorpholine

English

Synthesis and fungicidal activity study of novel daphneolone analogs with 2, 6-dimethylmorpholine

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

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