Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (12): 3356-3362.DOI: 10.6023/cjoc201805053 Previous Articles     Next Articles



霍新玉a, 李文斌a, 张博雅a, 陈晓飞a, 周月婷b, 张洁a,c, 韩小强b, 代斌a   

  1. a 石河子大学化学化工学院 新疆兵团化工绿色过程重点实验室 石河子 832003;
    b 石河子大学农学院 新疆绿洲农业病虫害治理与植保资源利用自治区高校重点实验室 石河子 832003;
    c 新疆生产建设兵团工业技术研究院 石河子 832003
  • 收稿日期:2018-05-29 修回日期:2018-07-07 发布日期:2018-08-22
  • 通讯作者: 张洁, 韩小强,
  • 基金资助:


Synthesis and Fungicidal Evaluation of Novel β-Carboline-Benzimidazole and β-Carboline-Benzothiazole Hybrids

Huo Xinyua, Li Wenbina, Zhang Boyaa, Chen Xiaofeia, Zhou Yuetingb, Zhang Jiea,c, Han Xiaoqiangb, Dai Bina   

  1. a School of Chemistry and Chemical Engineering, Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi 832003;
    b Key Laboratory at Universities of Xinjiang Uygur Autonomous Region for Oasis Agricultural Pest Management and Plant Protection Resource Utilization, College of Agricultural, Shihezi University, Shihezi 832003;
    c Industrial Technology Research Institute, Xinjiang Production and Construction Corps, Shihezi 832003
  • Received:2018-05-29 Revised:2018-07-07 Published:2018-08-22
  • Contact: 10.6023/cjoc201805053,
  • Supported by:

    Project supported by the Scientific Research Innovation Project in Xinjiang Uygur Autonomous Region (No. XJGRI2017045), the National Students Innovation and Entrepreneuship Training Program (No. 201810759055), the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT15R46), and the Yangtze River Scholar Research Project of Shihezi University (No. CJXZ201601).

In order to discover novel compounds with biological activities, new molecular hybrids combining benzimidazole or its bioisostere benzothiazole with β-carboline were synthesized. The benzimidazole or benzothiazole scaffold was linked at position-1 with β-carboline which was further characterized by 1H NMR, 13C NMR and HRMS. All of the target compounds were evaluated in vitro for their antifungal activity against Rhizoctorzia solani, Fusarium oxysporum, Botrytis cinerea Pers., sunflower sclerotinia rot and rape sclerotinia rot by mycelia growth inhibition assay at 50 μg·mL-1. The preliminary results showed that most compounds exhibit mild inhibiting effect against all the tested strains. Among them, 1-(1H-benzo[d]-imida-zol-2-yl)-9-ethyl-β-carboline (4a), 1-(1H-benzo[d]imidazol-2-yl)-9-benzyl-β-carboline (4c) and 1-(1H-benzo[d]imidazol-2-yl)-9-(3-chlorobenzyl)-β-carboline (4e) showed satisfactory antifungal activity against sunflower sclerotinia rot, 1-(1H-benzo[d]-imidazol-2-yl)-9-ethyl-β-carboline (4a), 1-(1H-benzo[d]imidazol-2-yl)-9-n-butyl-β-carboline (4b), 1-(1H-benzo[d]imidazol-2-yl)-9-benzyl-β-carboline (4c), 1-(1H-benzo[d]imidazol-2-yl)-9-((perfluorophenyl)methyl)-β-carboline (4f), 1-(benzo[d]-thiazol-2-yl)-9-(3-chlorobenzyl)-β-carboline (5e) and 1-(benzo[d]thiazol-2-yl)-9-((perfluorophenyl)methyl)-β-carboline (5f) displayed excellent fungicidal activity against rape sclerotinia rot. Specifically, compound 4c exhibited broad-spectrum fungicidal activity against most of the tested fungi.

Key words: β-carboline, benzimidazole, benzothiazole, antifungal activity