Chinese Journal of Organic Chemistry >
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).
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.
Xie Guiying , Jin Wenbo , Zhao Yanqin , Cheng Yinan , Sun Bingjian , Sun Shujun , Wang Meizi , Wei Dandan , Li Honglian . Synthesis of Thiophene Carboxamide Derivatives and Inhibitory Activity against Gaeumannomyces graminis var. tritici.[J]. Chinese Journal of Organic Chemistry, 2014 , 34(6) : 1124 -1131 . DOI: 10.6023/cjoc201401036
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