Design, synthesis and antifungal activity evaluation of coumarin-3-carboxamide derivatives

被引:46
|
作者
Yu, Xiang [1 ]
Teng, Peng [1 ]
Zhang, Ya-Ling [1 ]
Xu, Zhao-Jun [1 ]
Zhang, Ming-Zhi [1 ]
Zhang, Wei-Hua [1 ]
机构
[1] Nanjing Agr Univ, Coll Sci, Jiangsu Key Lab Pesticide, Nanjing 210095, Jiangsu, Peoples R China
基金
国家重点研发计划;
关键词
Coumarin; Amide; Hydrazide; Synthesis; Antifungal activity; SAR; MICROWAVE-ASSISTED SYNTHESIS; METAL-FREE CONDITIONS; COUMARIN DERIVATIVES; BIOLOGICAL-ACTIVITY; MEDICINAL CHEMISTRY; ANALOGS; CYCLIZATION; ACIDS;
D O I
10.1016/j.fitote.2018.03.013
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of coumarin-3-carboxamides/hydrazides have been designed and synthesized, all the target compounds were evaluated in vitro for their antifungal activity against Botrytis cinerea, Alternaria solani, Gibberella zeae, Rhizoctorzia solani, Cucumber anthrax and Alternaria leaf spot, some of the designed compounds 4a-4g exhibited potential activity in the primary assays, this highlighted by the compounds 4a, 4d, 4e and 4f, EC50 values of which against Rhizoctorzia solani were as low as 1.80 mu g/mL, 2.50 mu g/mL, 2.25 mu g/mL and 2.10 mu g/mL, respectively, exhibiting more effective control with that of the positive control than Boscalid. Furthermore, compounds 4a and 4e represented equivalent antifungal activity with Boscalid against Botrytis cinerea.
引用
收藏
页码:387 / 395
页数:9
相关论文
共 50 条
  • [1] Synthesis and Biological Activity Evaluation of Coumarin-3-Carboxamide Derivatives
    Phutdhawong, Weerachai
    Chuenchid, Apiwat
    Taechowisan, Thongchai
    Sirirak, Jitnapa
    Phutdhawong, Waya S.
    MOLECULES, 2021, 26 (06):
  • [2] SYNTHESIS AND ANTIMICROBIALLY ACTIVITIES OF COUMARIN-3-CARBOXAMIDE DERIVATIVES
    Celik-Onar, Huelya
    Bayramoglu, Goekce
    Mataraci-Kara, Emel
    REVUE ROUMAINE DE CHIMIE, 2023, 68 (1-2) : 85 - 89
  • [3] Efficient Synthesis of Novel 3-Substituted Coumarin-3-carboxamide
    Sheikhhosseini, Enayatollah
    Balalaie, Saeed
    Bigdeli, Mohammad Ali
    Habibi, Azizollah
    Moghaddam, Hamed Piri
    JOURNAL OF THE KOREAN CHEMICAL SOCIETY-DAEHAN HWAHAK HOE JEE, 2014, 58 (02): : 186 - 192
  • [4] Identification of coumarin-3-carboxamide derivatives as potential anti-tuberculosis agents
    Giri, Rajan Shobhanath
    Petukhova, Valentina
    Sun, Yongmao
    Klein, Larry L.
    Wan, Baojie
    Song, Yang
    Kim, Minje
    Cho, Sang H.
    Peng, Kuan Wei
    Wang, Yuehong
    Franzblau, Scott G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [5] Crystal structures of three 6-substituted coumarin-3-carboxamide derivatives
    Gomes, Ligia R.
    Low, John Nicolson
    Fonseca, Andre
    Matos, Maria Joao
    Borges, Fernanda
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2016, 72 : 926 - +
  • [6] Design, synthesis, antifungal activity, and 3D-QSAR of coumarin derivatives
    Wei, Yan
    Peng, Wei
    Wang, Dong
    Hao, Shuang-Hong
    Li, Wen-Wen
    Ding, Fei
    JOURNAL OF PESTICIDE SCIENCE, 2018, 43 (1-2) : 88 - 95
  • [7] Design, Synthesis and Antifungal Activity of Coumarin Ring-Opening Derivatives
    Zhang, Ming-Zhi
    Zhang, Yu
    Wang, Jia-Qun
    Zhang, Wei-Hua
    MOLECULES, 2016, 21 (10)
  • [8] Design, synthesis, and antifungal activity of novel cinnamon-pyrazole carboxamide derivatives
    Ren, Zi-Li
    Liu, Hao
    Jiao, Di
    Hu, Hao-Tian
    Wang, Wei
    Gong, Jie-Xiu
    Wang, Ai-Li
    Cao, Hai-Qun
    Lv, Xian-Hai
    DRUG DEVELOPMENT RESEARCH, 2018, 79 (06) : 307 - 312
  • [9] Design, Synthesis and Antifungal Activity of Novel Pyrazole-Thiophene Carboxamide Derivatives
    Li, Anbang
    Li, Zhongshan
    Zhao, Yang
    Yao, Tingting
    Cheng, Jingli
    Zhao, Jinhao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (09) : 2836 - 2844
  • [10] 1,1′-Carbonyldiimidazole (CDI) Mediated Facile Synthesis, Structural Characterization, Antimicrobial Activity, and in-silico Studies of Coumarin-3-carboxamide Derivatives
    Salar, Uzma
    Khan, Khalid M.
    Fakhri, Muhammad I.
    Hussain, Shafqat
    Tauseef, Saima
    Ameer, Shagufta
    Wadood, Abdul
    Khan, Huma
    Perveen, Shahnaz
    MEDICINAL CHEMISTRY, 2018, 14 (01) : 86 - 101