Synthesis, crystal structure and antifungal activities of new quinoline derivatives

被引:7
作者
Sun, Xin-Peng [1 ,3 ]
Yu, Wei [1 ,3 ]
Min, Li-Jing [2 ]
Han, Liang [1 ]
Sun, Na-Bo [3 ]
Liu, Xing-Hai [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Peoples R China
[2] Huzhou Univ, Coll Life Sci, Key Lab Vector Biol & Pathogen Control Zhejiang Pr, Huzhou 313000, Zhejiang, Peoples R China
[3] Zhejiang Shuren Univ, Coll Biol & Environm Engn, Hangzhou 310015, Zhejiang, Peoples R China
关键词
Quinoline; Synthesis; Diphenyl ether; Antifungal activity; HERBICIDAL ACTIVITY; DESIGN;
D O I
10.1016/j.molstruc.2022.134792
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A series of new quinoline ester derivatives containing diphenyl ether motif were designed and synthesized using 4-chlorophenol, 1-chloro-2-nitrobenzene, as raw materials via four steps. The structures were confirmed by 1 H NMR and HRMS. The compound 8-(4-chlorophenoxy)-2,3-dimethylquinolin-4-(4-chloro) benzoate (4j) exhibited moderate fungicidal activity (68.2% inhibition) against the plant pathogens Sclerotinia sclerotiorum at 50 mu g/mL.(c) 2022 Elsevier B.V. All rights reserved.
引用
收藏
页数:6
相关论文
共 38 条
[21]   Quinoline-based compounds as modulators of HIV transcription through NF-κB and Sp1 inhibition [J].
Miguel Bedoya, Luis ;
Jose Abad, Maria ;
Calonge, Esther ;
Astudillo Saavedra, Luis ;
Gutierrez C, Margarita ;
Kouznetsov, Vladimir V. ;
Alcami, Jose ;
Bermejo, Paulina .
ANTIVIRAL RESEARCH, 2010, 87 (03) :338-344
[22]   Novel Dioxolane Ring Compounds for the Management of Phytopathogen Diseases as Ergosterol Biosynthesis Inhibitors :Synthesis, Biological Activities, and Molecular Docking [J].
Min, Li-Jing ;
Wang, Han ;
Bajsa-Hirschel, Joanna ;
Yu, Chen-Sheng ;
Wang, Bin ;
Yao, Meng-Meng ;
Han, Liang ;
Cantrell, Charles L. ;
Duke, Stephen O. ;
Sun, Na-Bo ;
Liu, Xing-Hai .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2022, 70 (14) :4303-4315
[23]   Synthesis and anti-HIV properties of new hydroxyquinoline-polyamine conjugates on cells infected by HIV-1 LAV and HIV-1BaL viral strains [J].
Moret, Vincent ;
Dereudre-Bosquet, Nathalie ;
Clayette, Pascal ;
Laras, Younes ;
Pietrancosta, Nicolas ;
Rolland, Amandine ;
Weck, Clement ;
Marc, Sylvain ;
Kraus, Jean-Louis .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (23) :5988-5992
[24]   Synthesis of new series of quinoline derivatives with insecticidal effects on larval vectors of malaria and dengue diseases [J].
Murugan, Kadarkarai ;
Panneerselvam, Chellasamy ;
Subramaniam, Jayapal ;
Paulpandi, Manickam ;
Rajaganesh, Rajapandian ;
Vasanthakumaran, Murugan ;
Madhavan, Jagannathan ;
Shafi, S. Syed ;
Roni, Mathath ;
Portilla-Pulido, Johan S. ;
Mendez, Stelia C. ;
Duque, Jonny E. ;
Wang, Lan ;
Aziz, Al Thabiani ;
Chandramohan, Balamurugan ;
Dinesh, Devakumar ;
Piramanayagam, Shanmughavel ;
Hwang, Jiang-Shiou .
SCIENTIFIC REPORTS, 2022, 12 (01)
[25]   Synthesis and Fungicidal Activities of 2,3-Dimethyl-4-(1-acyloxy)alkoxy-6-tert-butyl-8-fluoroquinolines [J].
Pei, Dan ;
Zhang, Fan ;
Liu, Jie ;
Zhang, Dong-Lin ;
Yang, Ren ;
Zhong, Liang-Kun ;
Tan, Cheng-Xia ;
Xu, Tian-Ming .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (04) :1383-1387
[26]   Recent advances in the synthesis of quinolines: a review [J].
Prajapati, Shraddha M. ;
Patel, Kinjal D. ;
Vekariya, Rajesh H. ;
Panchal, Shyamali N. ;
Patel, Hitesh D. .
RSC ADVANCES, 2014, 4 (47) :24463-24476
[27]  
Pullagura M. K. P., 2016, International Journal of Pharmacy and Pharmaceutical Sciences, V8, P22
[28]   Synthesis, characterization and bioactivity of novel 8-hydroxyquinoline derivatives: Experimental, molecular docking, DFT and POM analyses [J].
Rbaa, Mohamed ;
Haida, Sara ;
Tuzun, Burak ;
Hichar, Abdelhadi ;
El Hassane, Anouar ;
Kribii, Abderahim ;
Lakhrissi, Younes ;
Ben Hadda, Taibi ;
Zarrouk, Abdelkader ;
Lakhrissi, Brahim ;
Berdimurodov, Elyor .
JOURNAL OF MOLECULAR STRUCTURE, 2022, 1258
[29]   Iron chelation and inhibition of metallopeptidases mediate anti-Trichomonas vaginalis activity by a novel 8-hydroxyquinoline derivative [J].
Rigo, Graziela Vargas ;
Joaquim, Angelica Rocha ;
Macedo, Alexandre Jose ;
de Andrade, Saulo Fernandes ;
Tasca, Tiana .
BIOORGANIC CHEMISTRY, 2022, 125
[30]  
Runge F. F., 1834, ANN PHYS, V31, P65, DOI [DOI 10.1002/ANDP.18341070502.(IN, DOI 10.1002/ANDP.18341070502]