噻吩甲酰胺衍生物的合成及其对小麦全蚀病病原菌的抑制活性
收稿日期: 2014-01-22
修回日期: 2014-02-21
网络出版日期: 2014-03-12
基金资助
国家“十二五”粮食丰产科技工程（Nos. 2011BAD16B07，2012BAD04B07）及中国科学院现代农业示范和区域创新集群计划（No. CXJQ120111）资助项目.
Synthesis of Thiophene Carboxamide Derivatives and Inhibitory Activity against Gaeumannomyces graminis var. tritici.
Received date: 2014-01-22
Revised date: 2014-02-21
Online published: 2014-03-12
Supported by
Project supported by the National Food Production Technology Project of China during the Twelfth Five-Year Period (Nos. 2011BAD16B07, 2012BAD04B07) and the Modern Agriculture Demonstration and Regional Innovation Cluster Plan Project of the Chinese Academy of Sciences (No. CXJQ120111).
谢桂英 , 靳文波 , 赵艳芹 , 程绎南 , 孙炳剑 , 孙淑君 , 汪梅子 , 位丹丹 , 李洪连 . 噻吩甲酰胺衍生物的合成及其对小麦全蚀病病原菌的抑制活性[J]. 有机化学, 2014 , 34(6) : 1124 -1131 . DOI: 10.6023/cjoc201401036
The procedures for synthesizing the substituted ester 2-hydrothiophene-3-carboxylate and its silanization were explored. The reaction conditions were optimized. And with the substituted thiophene as the framework, 20 new thiophene carboxamide derivatives were synthesized. The chemical structures of thiophene carboxamide derivatives were confirmed by 1H NMR, 13C NMR, HRMS or elemental analysis techniques. The inhibitory activity against Gaeumannomyces graminis var. tritici was evaluated in vitro by the plate method. The preliminary structure-activity relationship indicated that the substituent bonded to the amide nitrogen atom and the steric hindrance of the substituent at 2nd position of the thiophene carboxamide had a significant influence on the activity. The compounds 7b～7d, 7l, 7m and 7o exhibited very high inhibitory activity. The results would be helpful for the design of lead compounds.
[1] Cook, R. J. Physiol. Mol. Plant Pathol. 2003, 62, 73.
[2] Wang, B. T.; Shang, H. S.; Li, Q.; Wang, F.; Li, G. B. Acta Agric. Boreali-Occident. Sin. 2005, 14, 26 (in Chinese).
(王保通, 商鸿生, 李强, 王芳, 李高宝, 西北农业学报, 2005, 14, 26.)
[3] Freeman, J.; Ward, E. Mol. Plant Pathol. 2004, 5, 235.
[4] Phillion, D. P.; Sant, K. A. V.; Walker, D. M. WO 9524380, 1995 [Chem. Abstr. 1995, 124, 116873]. [5] Phillion, D. P.; Braccolino, D. S.; Graneto, M. J.; Phillips, W. G.; Sant, K. A. V.; Walker, D. M.; Wong, S. C. EP 538231, 1993 [Chem. Abstr. 1993, 119, 160256].
[6] Phillion, D. P.; Graneto, M. J.; Pratt, J. K.; Wong, S. C. CA 2121917, 1994 [Chem. Abstr. 1995, 122, 213924].
[7] Phillion, D.; Wong, S. C.; Shortt, B. US 5486621, 1996 [Chem. Abstr. 1996, 124, 253325].
[8] Moloney, B. A.; Hardy, D.; Saville-Stones, E. A. WO 9942447, 1999 [Chem. Abstr. 1999, 131, 170272].
[9] Mansfield, D. J.; Cooke, T.; Thomas, P. S.; Vors, J. P.; Coqueron, P. Y.; Briggs, G. G.; Lachaise, H. EP 1389614, 2004 [Chem. Abstr. 2004, 140, 181332].
[10] Michelotti, E. L.; Young, D. H. US 5304572, 1994 [Chem. Abstr. 1994, 121, 76155].
[11] Wu, Q.; Wu, Q.; Zhang, Q.; Yang J. C.; Liu, C. L. Agrochemicals 2010, 49, 5 (in Chinese).
(吴峤, 伍强, 张茜, 杨吉春, 刘长令, 农药, 2010, 49, 5.)
[12] Li, L.; Gu, F. L.; Zhu, K.; Qiu, H. Y. J. Hangzhou Normal Univ. (Nat. Sci.) 2011, 10, 52 (in Chinese).
(李莉, 顾峰雷, 诸坤, 邱化玉, 杭州师范大学学报(自然科学版), 2011, 10, 52.)
[13] Hu, Y. G.; Lu, M. Y.; Song, H. L.; Ding, M. W. Chin. J. Org. Chem. 2005, 25, 295 (in Chinese).
(胡扬根, 吕茂云, 宋鹤丽, 丁明武, 有机化学, 2005, 25, 295.)
[14] Liao, Q. B.; Liu, M. G.; Yu, L.; Zhu, M.; Ding, M. W. Chin. J. Org. Chem. 2009, 29, 1582 (in Chinese).
(廖全斌, 刘明国, 喻兰, 朱敏, 丁明武, 有机化学, 2009, 29, 1582.)
[15] Phillips, G.; Fevig, T. L.; Lau, P. H.; Klemm, G. H.; Mao, M. K.; Ma, C.; Gloeckner, J. A.; Clark, A. S. Org. Proc. Res. Dev. 2002, 6, 357.
[16] Fevig, T. L.; Pillips, W. G.; Lau, P. H. J. Org. Chem. 2001, 66, 2493.
[17] Pillips, W. G.; Mao, M. K.; Ma, C.; Fevig, T. L. WO 9962915, 1999 [Chem. Abstr. 1999, 132, 23082].
[18] Mannam, S.; Sekar, G. Tetrahedron Lett. 2008, 49, 2457.
[19] Shi, M.; Wang, C. J. J. Chem. Res. 2004, 107.
[20] Hermeling, D.; Schafer, H. J. Chem. Ber. 1988, 121, 1151.
[21] Bohlmann, F.; Bresinsky, E. Chem. Ber. 1964, 97, 2109.
[22] Matsuya, Y.; Hayashi, K.; Wada, A.; Nemoto, H. J. Org. Chem. 2008, 73, 1987.
[23] Baharfar, R.; Baghbaniana, S. M.; Hosseinnia, R.; Bijanzadeh, H. R. Lett. Org. Chem. 2007, 4, 567.
[24] Roth, F.; Gygax, P.; Fráter, G. Tetrahedron Lett. 1992, 33, 1045.
[25] Sun, B. J.; Yuan, H. X.; Xing, X. P.; Li, H. L. J. Triticeae Crops 2008, 28, 709 (in Chinese).
(孙炳剑, 袁虹霞, 邢小萍, 李洪连, 麦类作物学报, 2008, 28, 709.)
[26] Hawker, D. D.; Silverman, R. B. Bioorg. Med. Chem. 2012, 20, 5763.
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