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

doi:10.6023/cjoc201805053

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

Notes

含苯并咪(噻)唑环的β-咔啉衍生物的合成与杀菌活性

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

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 E-mail:zhangjie-xj@163.com,hanshz@shzu.edu.cn
基金资助:
新疆维吾尔自治区研究生科研创新项目基金（No.XJGRI2017045）、国家大学生创新创业训练计划（No.201810759055）、教育部长江学者和创新团队发展计划（No.IRT15R46）及石河子大学长江学者研究（No.CJXZ201601）资助项目.

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

Huo Xinyu^a, Li Wenbin^a, Zhang Boya^a, Chen Xiaofei^a, Zhou Yueting^b, Zhang Jie^a,c, Han Xiaoqiang^b, Dai Bin^a

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 E-mail:zhangjie-xj@163.com,hanshz@shzu.edu.cn
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).

1. Synthesis and Fungicidal Evaluation of Novel β-Carboline-Benzimidazole and β-Carboline-Benzothiazole Hybrids.PDF(1331KB)

Abstract

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

Cite this article

Huo Xinyu, Li Wenbin, Zhang Boya, Chen Xiaofei, Zhou Yueting, Zhang Jie, Han Xiaoqiang, Dai Bin. Synthesis and Fungicidal Evaluation of Novel β-Carboline-Benzimidazole and β-Carboline-Benzothiazole Hybrids[J]. Chin. J. Org. Chem., 2018, 38(12): 3356-3362.

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含苯并咪(噻)唑环的β-咔啉衍生物的合成与杀菌活性

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

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