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Synthesis, Structure and Biological Activities of 2,2-Dichloro-1-(4-ethoxyphenyl)- cyclopropanyl Substituted Piperidin-1-yl Ketone
Corresponding Author(s) : Na-Bo Sun
Asian Journal of Chemistry,
Vol. 25 No. 7 (2013): Vol 25 Issue 7
Abstract
Ten new amide-type compounds, which are pyrethroids containing piperidine, are synthesized from 1-(4-ethyoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid and substituted piperidine. Their structures were confirmed by 1H NMR, MS and elemental analysis. The crystal structure of 4a and 4h were determined by X-ray diffraction analysis. The bioassay results indicated that they showed moderate activity.
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- a) X.H. Liu, C.X. Tan, J.Q. Weng and H.J. Liu, Acta Cryst., E68, o493(2012); b) X.H. Liu, P.Q. Chen, B.L. Wang, Y.H. Li and Z.M. Li, Bioorg. Med. Chem. Lett., 17, 3784 (2007); c) X.H. Liu, P.Q. Chen, F.Q. He, Y.H. Li, S.H. Wang and Z.M. Li, Struct. Chem., 5, 563 (2007); d) X.H. Liu, C.Y. Zhang, W.C. Guo, Y.H. Li, P.Q. Chen, T. Wang, W.L. Dong, B.L. Wang, H.W. Sun and Z.M. Li, J. Enzym. Inhib. Med. Chem., 24, 545 (2009); e) X.H. Liu, Y.X. Shi, Y. Ma, G.R. He, W.L. Dong, C.Y. Zhang, B.L. Wang, S.H. Wang, B.J. Li and Z.M. Li, Chem. Biol. Drug Des., 73, 320 (2009); f) X.H. Liu, Y.X. Shi, Y. Ma, C.Y. Zhang, W.L. Dong, P. Li, B.L. Wang, B.J. Li and Z.M. Li, Eur. J. Med. Chem., Vol. 25, No. 7 (2013) Synthesis, Structure and Biological Activities of Substituted Piperidin-1-yl Ketone 4069 44, 2782 (2009); g) X.H. Liu, J.Q. Weng, C.X. Tan, L. Pan, B.L. Wang and Z.M. Li, Asian J. Chem., 23, 4031 (2011); h) H.J. Liu, J.Q. Weng, C.X. Tan and X.H. Liu, Acta Cryst., E67, o1940 (2011).
- a) X.H. Liu, L. Pan, J.Q. Weng, C.X. Tan, Y.H. Li, B.L. Wang and Z.M. Li, Mol. Divers., 16,251(2012); b) C.X. Tan, Y.X. Shi, J.Q. Weng, X.H. Liu, B.J. Li and W.G. Zhao, Lett. Drug Des. Discov., 9, 431 (2012); c) X.H. Liu, L. Pan, C.X. Tan, J.Q. Weng, B.L. Wang and Z.M. Li, Pestic. Biochem. Physiol., 101, 143 (2011); d) C.X. Tan, Y.X. Shi, J.Q. Weng, X.H. Liu, B.J. Li and W.G. Zhao, J. Heterocycl. Chem., DOI:10.1002/jhet.1656.
- K. Matsuda, K. Iharada, K.H. Suzuki, M. Yamashita, H. Okimoto, K. Nishimura, K.T. Ueno and K. Komai, J. Pestic. Sci., 20, 487 (1995).
- a) X.H. Liu, C.X. Tan and J.Q. Weng, Phosphorus Sulfur Silicon Rel. Elem., 186, 552 (2011); b) X.H. Liu, C.X. Tan and J.Q. Weng, Phosphorus Sulfur Silicon Rel. Elem., 186, 558 (2011); c) X.H. Liu, L. Pan, Y. Ma, J.Q. Weng, C.X. Tan, Y.H. Li, Y.X. Shi, B.J. Li, Z.M. Li and Y.G. Zhang, Chem. Biol. Drug Des., 78, 689 (2011); d) P.Q. Chen, C.X. Tan, J.Q. Weng and X.H. Liu, Asian J. Chem., 24, 2808 (2012); e) J.Q. Weng, C.X. Tan, L. Wang and X.H. Liu, J. Chem. Soc. Pak., 34, 1248(2012); f) Y.L. Xue, Y.G. Zhang and X.H. Liu, Asian J. Chem., 24, 3016 (2012); g) Y.L. Xue, Y.G. Zhang and X.H. Liu, Asian J. Chem., 24, 1571 (2012); h) X.F. Liu and X.H. Liu, Acta Cryst., E67, o202 (2011).
- Bruker, Smart-NT. Version 5.05 Bruker AXS inc, Madsion, Wisconsin, USA (1998)
References
a) X.H. Liu, C.X. Tan, J.Q. Weng and H.J. Liu, Acta Cryst., E68, o493(2012); b) X.H. Liu, P.Q. Chen, B.L. Wang, Y.H. Li and Z.M. Li, Bioorg. Med. Chem. Lett., 17, 3784 (2007); c) X.H. Liu, P.Q. Chen, F.Q. He, Y.H. Li, S.H. Wang and Z.M. Li, Struct. Chem., 5, 563 (2007); d) X.H. Liu, C.Y. Zhang, W.C. Guo, Y.H. Li, P.Q. Chen, T. Wang, W.L. Dong, B.L. Wang, H.W. Sun and Z.M. Li, J. Enzym. Inhib. Med. Chem., 24, 545 (2009); e) X.H. Liu, Y.X. Shi, Y. Ma, G.R. He, W.L. Dong, C.Y. Zhang, B.L. Wang, S.H. Wang, B.J. Li and Z.M. Li, Chem. Biol. Drug Des., 73, 320 (2009); f) X.H. Liu, Y.X. Shi, Y. Ma, C.Y. Zhang, W.L. Dong, P. Li, B.L. Wang, B.J. Li and Z.M. Li, Eur. J. Med. Chem., Vol. 25, No. 7 (2013) Synthesis, Structure and Biological Activities of Substituted Piperidin-1-yl Ketone 4069 44, 2782 (2009); g) X.H. Liu, J.Q. Weng, C.X. Tan, L. Pan, B.L. Wang and Z.M. Li, Asian J. Chem., 23, 4031 (2011); h) H.J. Liu, J.Q. Weng, C.X. Tan and X.H. Liu, Acta Cryst., E67, o1940 (2011).
a) X.H. Liu, L. Pan, J.Q. Weng, C.X. Tan, Y.H. Li, B.L. Wang and Z.M. Li, Mol. Divers., 16,251(2012); b) C.X. Tan, Y.X. Shi, J.Q. Weng, X.H. Liu, B.J. Li and W.G. Zhao, Lett. Drug Des. Discov., 9, 431 (2012); c) X.H. Liu, L. Pan, C.X. Tan, J.Q. Weng, B.L. Wang and Z.M. Li, Pestic. Biochem. Physiol., 101, 143 (2011); d) C.X. Tan, Y.X. Shi, J.Q. Weng, X.H. Liu, B.J. Li and W.G. Zhao, J. Heterocycl. Chem., DOI:10.1002/jhet.1656.
K. Matsuda, K. Iharada, K.H. Suzuki, M. Yamashita, H. Okimoto, K. Nishimura, K.T. Ueno and K. Komai, J. Pestic. Sci., 20, 487 (1995).
a) X.H. Liu, C.X. Tan and J.Q. Weng, Phosphorus Sulfur Silicon Rel. Elem., 186, 552 (2011); b) X.H. Liu, C.X. Tan and J.Q. Weng, Phosphorus Sulfur Silicon Rel. Elem., 186, 558 (2011); c) X.H. Liu, L. Pan, Y. Ma, J.Q. Weng, C.X. Tan, Y.H. Li, Y.X. Shi, B.J. Li, Z.M. Li and Y.G. Zhang, Chem. Biol. Drug Des., 78, 689 (2011); d) P.Q. Chen, C.X. Tan, J.Q. Weng and X.H. Liu, Asian J. Chem., 24, 2808 (2012); e) J.Q. Weng, C.X. Tan, L. Wang and X.H. Liu, J. Chem. Soc. Pak., 34, 1248(2012); f) Y.L. Xue, Y.G. Zhang and X.H. Liu, Asian J. Chem., 24, 3016 (2012); g) Y.L. Xue, Y.G. Zhang and X.H. Liu, Asian J. Chem., 24, 1571 (2012); h) X.F. Liu and X.H. Liu, Acta Cryst., E67, o202 (2011).
Bruker, Smart-NT. Version 5.05 Bruker AXS inc, Madsion, Wisconsin, USA (1998)