Design, Synthesis and Biological Activities of Novel Dual-Chiral Carbon and Sulfur Pyridine Phthalic Acid Diamide Derivatives
- Corresponding author: Zhou Sha, mengsha171657@163.com Li Zhengming, nkzml@vip.163.com
Citation:
Meng Xiangde, Zhou Sha, Xie Yongtao, Zhao Yu, Xiong Lixia, Zhou Sha, Li Zhengming. Design, Synthesis and Biological Activities of Novel Dual-Chiral Carbon and Sulfur Pyridine Phthalic Acid Diamide Derivatives[J]. Chinese Journal of Organic Chemistry,
;2017, 37(4): 908-913.
doi:
10.6023/cjoc201610027
George, L. P.; Thomas, S. M.; Thomas, S. P.; John, F. H.; Daniel, C.; Lindsey, F.; Cheryl, B. A.; Christine, D. M.; Ben, S. K.; Kenneth, H. A.; Hollingshaus, J. G.; Christopher, C. E.; Eric, B. A. Bioorg. Med. Chem. Lett. 2007, 17, 6274.
doi: 10.1016/j.bmcl.2007.09.012
Hughes, K. A.; Lahm, G. P.; Selby, T. P.; Stevenson, T. M. WO 2004067528, 2004[Chem. Abstr. 2004, 141, 190786].
Lahm, G. P.; Cordova, D.; Barry, J. D. Bioorg. Med. Chem. 2009, 17, 4127.
doi: 10.1016/j.bmc.2009.01.018
Li, Y.; G, J.-J.; Han, F.; Hu, M. Anhui Chem. Ind. 2015, 6, 3 (in Chinese).
doi: 10.3969/j.issn.1008-553X.2015.04.002
Zhou, S.; Jia, Z.-H.; Xiong, L.-X.; Yan, T.; Yang, N.; Wu, G.-P.; Song, H.-B.; Li, Z.-M. J. Agric. Food Chem. 2014, 62(27), 6269.
doi: 10.1021/jf501727k
Zhou, S.; Gu, Y.-C.; Liu, M.; Wu, C.-C.; Zhao, Y.; Jia, Z.-H.; Wang, B.-L.; Xiong, L.-X.; Yang, N.; Li, Z.-M. J. Agric. Food Chem. 2014, 62(46), 11054.
doi: 10.1021/jf503513n
Zhou, S.; Yan, T.; Li, Y.-X.; Jia, Z.-H.; Wang, B.-L; Zhao, Y.; Qiao, Y.-Y.; Xiong, L.-X.; Li, Y.-Q.; Li, Z.-M. Org. Biomol. Chem. 2014, 12, 6643.
doi: 10.1039/C4OB00716F
Zhou, S.; Yan, T.; Zhou, S.; Hua, X.-W.; Wang, B.-L.; Gu, Y.-C.; Xiong, L.-X.; Li, Y.-Q.; Li, Z.-M. Chin. J. Chem. 2014, 32(7), 567.
doi: 10.1002/cjoc.201400223
Gnamm, C.; Jeanguenat, A.; Dutton, A. C.; Grimm, C.; Kloer, D. P.; Crossthwaite, A. J. Bioorg. Med. Chem. Lett. 2012, 22, 3800.
doi: 10.1016/j.bmcl.2012.03.106
Sergiy, P. WO 2007022900, 2007[Chem. Abstr. 2004, 146, 273965].
Masanobu, O.; Akihiko, Y.; Eiji, K. EP 1006102, 2000[Chem. Abstr. 2004, 133, 30570].
Graham, A. J.; Yang, S.; William, D. A. Eur. J. Med. Chem. 2002, 37, 825.
doi: 10.1016/S0223-5234(02)01406-X
Soucy, C.; Favreau, D.; Kayser, M. M. J. Org. Chem. 1987, 52, 129.
doi: 10.1021/jo00377a023
Wei, R.-B.; Li, S.-W.; Lu, J.-K.; Zheng, S.-H.; Hu, W.-H. Dyest. Ind. 2000, 37, 16.
Michael, L. R.; Benjamin, N. M.; Jim, H. X.; Richard, R. B.; Zhu, Y. M.; James, R. M.; Vidyadhar, H. B.; Joseph, D. J. WO 2007095229, 2007[Chem. Abstr. 2007, 147, 270793].
David E, P.; Rnonald, R.; James R, M. US 20080207910, 2008[Chem. Abstr. 2008, 149, 307682].
Douglas C, B.; Timothy J, A.; David E, P. US 8193222, 2012[Chem. Abstr. 2012, 157, 45017].
Huang, J.-X.; Rogers, R. B.; Orr, N. WO 2007149134, 2007[Chem. Abstr. 2007, 148, 47562].
Wu, Y.-D.; Shen, J.-L.; Chen, J.; Lin, X.-W.; Li, A.-M. Plant Prot. 1996, 22, 3 (in Chinese).
Busivine, J. R. FAO Plant Production and Protection Paper 21, FAO, Rome, 1980, p. 3.
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