Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (12): 2642-2649.DOI: 10.6023/cjoc201506027 Previous Articles     Next Articles



刘斌, 孔令青, 董宏波, 王明安   

  1. 中国农业大学应用化学系 北京 100193
  • 收稿日期:2015-06-24 修回日期:2015-08-17 发布日期:2015-08-26
  • 通讯作者: 王明安
  • 基金资助:

    国家自然科学基金(No. 20772150)和国家十二五科技支撑计划(No. 2011BAE06B04)资助项目.

Synthesis and Herbicidal Activity of Adenylosuccinate Aynthetase Bisubstrate Hybrid Inhibitor Analogues

Liu Bin, Kong Lingqing, Dong Hongbo, Wang Ming'an   

  1. Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2015-06-24 Revised:2015-08-17 Published:2015-08-26
  • Supported by:

    Project supported by National Natural Science foundation of China (No. 20772150) and National KeyTechnologies R&D Program of China (No. 2011BAE06B04).

The adenylosuccinate synthetase (AdSS) bisubstrate hybrid inhibitor analogues 5-(4-hydroxybenzyl)-N3- [5-ethoxycarbonyl-4-(N-formylhydroxyamino)pentyl]-hydantoin benzoates containing the structural moiety of hadacidin were designed and synthesized via Claisen condensation, hydrolysis decarbosylation, imidization, acid-catalyzed ring closure, borane reduction, Mitsunobu coupling reaction, formylation and deprotection used 1,4-butyrolactone as raw materials. Their structures were characterized with 1H NMR and HR-ESI-MS data. The preliminary and greenhouse test results showed that these compounds only exhibited weak inhibition against E. rusgalli and B. campestris at the concentration of 100 μg/mL.

Key words: adenylosuccinate synthetase, bisubstrate hybrid inhibitor, hadacidin, synthesis, herbicidal activities