有机化学 ›› 2015, Vol. 35 ›› Issue (12): 2642-2649.DOI: 10.6023/cjoc201506027 上一篇    下一篇

研究简报

腺苷酸琥珀酸合成酶双基抑制剂类似物的合成及生物活性

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 E-mail:wangma@cau.edu.cn
  • 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).

以丁内酯为原料, 通过缩合、水解、亚胺化、关环、还原、偶联、甲酰化以及脱保护等反应设计并探索了腺苷酸琥珀酸合成酶双基抑制剂类似物的合成方法, 目标化合物的结构经1H NMR和HR-ESI-MS数据进行表征. 初步生物活性测试结果表明, 目标化合物在100 μg/mL浓度下对油菜和稗草具有较弱的抑制活性.

关键词: 腺苷酸琥珀酸合成酶, 双基抑制剂, Hadacidin, 合成, 除草活性

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