Design, synthesis, and antifungal activity of flavonoid derivatives containing thiazole moiety

被引:12
作者
Meng, Fei [1 ]
Yan, Zixin [1 ]
Lu, Yuexiao [1 ]
Wang, Xiaobin [2 ]
机构
[1] Yangzhou Univ, Coll Hort & Plant Protect, Inst Pesticide, Yangzhou 225009, Jiangsu, Peoples R China
[2] Jiangsu Ocean Univ, Coll Pharm, Lianyungang 222005, Peoples R China
关键词
Flavonoid; Thiazole; Synthesis; Antifungal activity; ANTICANCER; DISCOVERY; CITRUS;
D O I
10.1007/s11696-022-02522-4
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of flavonoid derivatives containing thiazole scaffold were designed, synthesized and evaluated for their inhibition effects against Rhizoctonia solani, Fusarium graminearum, Gaeumannomyces graminis, Alternaria solani, Botrytis cinerea, and Alternaria mali. The antifungal bioassays results in vitro indicated that some target compounds showed good antibacterial activity against the tested plant fungi, which were better than that of the flavonoid natural product quercetin. Strikingly, the title compounds 6a, 6b, and 6f demonstrated obvious antifungal activities against Rhizoctonia solani with EC50 value of 9.6, 35.5, and 21.5 mu g/mL, respectively. The EC50 value of compound 6b against Gaeumannomyces graminis reached 2.7 mu g/mL. [GRAPHICS] .
引用
收藏
页码:877 / 885
页数:9
相关论文
共 24 条
[1]   A novel transdermal patch incorporating meloxicam: In vitro and in vivo characterization [J].
Ah, Young-Chang ;
Choi, Jin-Kyu ;
Choi, Yang-Kyu ;
Ki, Han-Moi ;
Bae, Joon-Ho .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2010, 385 (1-2) :12-19
[2]   Anti-Fungal Efficacy and Mechanisms of Flavonoids [J].
Al Aboody, Mohammed Saleh ;
Mickymaray, Suresh .
ANTIBIOTICS-BASEL, 2020, 9 (02)
[3]   Update on uses and properties of Citrus flavonolds:: New findings in anticancer, cardiovascular, and anti-inflammatory activity [J].
Benavente-Garcia, O. ;
Castillo, J. .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2008, 56 (15) :6185-6205
[4]  
Bhatt D., 2016, INDO AM J PHARM RES, V6, P4345
[5]   NHC-Catalyzed Reaction of Enals with Hydroxy Chalcones: Diastereoselective Synthesis of Functionalized Coumarins [J].
Bhunia, Anup ;
Patra, Atanu ;
Puranik, Vedavati G. ;
Biju, Akkattu T. .
ORGANIC LETTERS, 2013, 15 (07) :1756-1759
[6]   Discovery of Novel Thiazole Carboxamides as Antifungal Succinate Dehydrogenase Inhibitors [J].
Guo, Xiaofeng ;
Zhao, Bin ;
Fan, Zhijin ;
Yan, Dongyan ;
Zhang, Nailou ;
Wu, Qifan ;
Yu, Bin ;
Zhou, Shuang ;
Kalinina, Tatiana A. ;
Belskaya, Nataliya P. .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2019, 67 (06) :1647-1655
[7]   Modulation of Anti-Oxidation Ability by Proanthocyanidins during Germination of Arabidopsis thaliana Seeds [J].
Jia, Li-Guo ;
Sheng, Zi-Wei ;
Xu, Wei-Feng ;
Li, Ying-Xuan ;
Liu, Ying-Gao ;
Xia, Yi-Ji ;
Zhang, Jian-Hua .
MOLECULAR PLANT, 2012, 5 (02) :472-481
[8]   Recent advances in natural antifungal flavonoids and their derivatives [J].
Jin, Yong-Sheng .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2019, 29 (19)
[9]   Ruthenium(II)-Catalyzed Synthesis of Spirobenzofuranones by a Decarbonylative Annulation Reaction [J].
Kaishap, Partha P. ;
Duarah, Gauri ;
Sarma, Bipul ;
Chetia, Dipak ;
Gogoi, Sanjib .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (02) :456-460
[10]  
Kayser Hartmut, 2007, V948, P67