Citation: CHEN Meihang, ZHANG Xun, WANG Xiaobin, CHEN Shixue, SHU Hua. Synthesis and Antibacterial Activity of 1-Aryl-3-(3-((2-oxo-2H-Chromen-4-yl)oxy)phenyl)thiourea Derivatives[J]. Chinese Journal of Applied Chemistry, ;2017, 34(7): 774-782. doi: 10.11944/j.issn.1000-0518.2017.07.160427 shu

Synthesis and Antibacterial Activity of 1-Aryl-3-(3-((2-oxo-2H-Chromen-4-yl)oxy)phenyl)thiourea Derivatives

CHEN Meihang ^a,*,, ,
ZHANG Xun ^a ,
WANG Xiaobin ^b ,
CHEN Shixue ^a ,
SHU Hua ^a

a.
School of Material and Chemistry Engineering, Tongren University, Tongren, Guizhou 554300, China
b.
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering; Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education; Certer for Rearch and Development of Fine Chemicals, Guizhou University, Guiyang 550025, China

Corresponding author: CHEN Meihang, chenmeihang0123@126.com
Received Date: 25 October 2016
Revised Date: 29 November 2016
Accepted Date: 19 January 2017

Fund Project: Dr Fund of Tongren University trxyDH1618Natural Science Fund of Guizhou Province Education [2011]2080

Figures(1)

In order to develop thiourea derivatives with antibacterial activities, a series of novel 1-aryl-3-(3-((2-oxo-2H-chromen-4-yl)oxy)phenyl)thiourea derivative was synthesized from 4-hydroxycoumarin via chlorination, etherification, isothiocyanate formation and addition reactions. The structures of the title compounds were characterized by infrared spectroscopy(IR), nuclear magnetic resonance spectrocopy(NMR) and mass spectrometry(MS). The results show that title compounds exhibit excellent antibacterial activities against Xanthomonas oryzae pv. oryzae(Xoo) and Xanthomonas citri subsp. Citri(Xcc). Among of them, compounds 4k, 4l, 4m and 4n show excellent antibacterial activities against Xoo, with the EC₅₀ values 137.42, 131.05, 129.23 and 117.43 mg/L, respectively, which were better than that of the control agent thiodiazole-copper(195.24 mg/L). Compounds 4k, 4l, 4m and 4n display considerable antibacterial activities against Xcc, with the EC₅₀ values of 97.02, 94.31, 102.28 and 90.52 mg/L, respectively, which are better than that of thiodiazole-copper(120.25 mg/L).
- coumarin,
- thiourea derivatives,
- synthesis,
- antibacterial activities
1. [1]
  CHEN Liang, LIU Junli. The New Tendency of Crops Bacterial Diseases Occur[J]. Pestic Mark News, 2010,20(31):48-50.
2. [2]
  ZUO Jinglong, JIANG Guixia. Bacterial Disease Prevention and Control of Major Chemical Reagents[J]. Jilin Veget, 2016,3:21-22.
3. [3]
  ZHOU Yuping, YANG Zhengyin, YU Hongjuan. Syntheses, Characterization and Bacteriostatic Activities of 1-Phenyl-3-methyl-4-benzoylpyrazolone-5-thiosemicarbazone and Its Rare Earth Complexes[J]. Chinese J Appl Chem, 1999,16(6):37-41.
4. [4]
  SU Guifa, HE Lini, QIN Jiangke. Synthesis and Antibacterial Activity of 1-Dehyoabicticacy-3-Aroylthiosem-Icarbazides Compounds and Their 1, 3, 4-Thiadiazole Derivatives[J]. Chinese J Appl Chem, 2008,25(7):803-807.
5. [5]
  Lu A D, Wang Z W, Zhou Z H. Application of "Hydrogen Bonding Interaction" in New Drug Development: Design, Synthesis, Antiviral Activity, and SARs of Thiourea Derivatives[J]. J Agric Food Chem, 2015,63(5):1378-1384. doi: 10.1021/jf505355r
6. [6]
  Ghorab M M, Alsaid M S, El-Gaby M S A. Biological Evaluation of Some New N-(2, 6-Dimethoxypyrimidinyl) Thioureido Benzenesulfonamide Derivatives as Potential Antimicrobial and Anticancer Agents[J]. Eur J Med Chem, 2016,124:299-310. doi: 10.1016/j.ejmech.2016.08.060
7. [7]
  Yapati H, Devineni S R, Chirumamilla S. Synthesis, Characterization and Studies on Antioxidant and Molecular Docking of Metal Complexes of 1-(Benzo[d]thiazol-2-yl)thiourea[J]. J Chem Sci, 2016,128(1):43-51.
8. [8]
  Chetana P R, Srinatha B S, Somashekar M N. Synthesis, Spectroscopic Characterisation, Thermal Analysis, DNA Interaction and Antibacterial Activity of Copper(Ⅰ) Complexes with N, N'-Disubstituted Thiourea[J]. J Mol Struct, 2016,1106:352-365. doi: 10.1016/j.molstruc.2015.10.010
9. [9]
  Kadir M A, Ramli R, Yusof M S M. Synthesis, Spectroscopic Studies and Antibacterial Activity of New Lauroyl Thiourea Amino Acid Derivatives[J]. Asian J Chem, 2016,28(3):596-600. doi: 10.14233/ajchem
10. [10]
  Khare R, Sharma J, Sharma A. Synthesis, Characterization, and Antibacterial Activity of Some Thiazoles Derived from Allylthioureas[J]. Russ J Gen Chem, 2016,86(3):702-707. doi: 10.1134/S1070363216030312
11. [11]
  WANG Cheng, WANG Runsheng, FENG Feng. Synthesis of a New Schiff Base Containing 4-Hydroxy Coumarin and Characterization of Its Antibacterial Activity[J]. Chem Reag, 2008,30(12):935-936. doi: 10.3969/j.issn.0258-3283.2008.12.018
12. [12]
  LIU Bin, XIE Longguan, XU Xiaohua. Synthesis, Crystal Structure and Herbicidal Activity of 3-Benzoyl-4-hydroxycoumarin Derivative[J]. Chinese J Org Chem, 2011,31(12):2067-2073.
13. [13]
  Cao D, Liu Y B, Yan W. Design, Synthesis, and Evaluation of in Vitro and in Vivo Anticancer Activity of 4-Substituted Coumarins:A Novel Class of Potent Tubulin Polymerization Inhibitors[J]. J Med Chem, 2016,59(12):5721-5739. doi: 10.1021/acs.jmedchem.6b00158
14. [14]
  Aws M, Hamdy A M, Khaddour Z. Synthesis of Arylated Coumarins by Suzuki-Miyaura Cross-Coupling. Reactions and Anti-HIV Activity[J]. Bioorg Med Chem, 2016,24(21):5115-5126. doi: 10.1016/j.bmc.2016.08.029
15. [15]
  Buzad C, Doherty M F. Design of Three-Component Kioetically Controlled Reactive Distillation Columus Using Fixed-Point Methods[J]. Chem Eng Sci, 1994,49(12):1947-1963. doi: 10.1016/0009-2509(94)80079-0
16. [16]
  XU Cuilian, CHEN Gang, XIA Baigen. Synthesis and Antibacterial Activity of Thiosemicarbazone Compounds Containing Coumarin-Skeleton[J]. Chem Bull, 2009,9:815-819.
17. [17]
  Chen M H, Tang B C, Zhang X. Synthesis and Antibacterial Activity Evaluation of Novel (E)-4-(4-((arylid-ene)amino)phenoxy)coumarin Derivatives[J]. J Heterocycl Chem, 2016.
18. [18]
  Rao M L N, Kumar A. Pd-Catalyzed Chemo-Selective Mono-Arylations and Bis-Arylations of Functionalized 4-Chlorocoumarins with Triarylbismuths as Threefold Arylating Reagents[J]. Tetrahedron, 2014,70(39):6995-7005. doi: 10.1016/j.tet.2014.07.059
19. [19]
  Xu W M, Han F F, He M. Inhibition of Tobacco Bacterial Wilt with Sulfone Derivatives Containing an 1, 3, 4-Oxadiazole Moiety[J]. J Agric Food Chem, 2012,60(4):1036-1041. doi: 10.1021/jf203772d
1. [1]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
2. [2]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
3. [3]
  Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007
4. [4]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
5. [5]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
6. [6]
  Ying Chen , Ronghua Yan , Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066
7. [7]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
8. [8]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
9. [9]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
10. [10]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
11. [11]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
12. [12]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
13. [13]
  Jia JI , Tengqi YAO , Wenqian DENG , Wenjing SHI , Xuan LÜ , Lin TIAN , Xiaoyan XIN , Yinling HOU . Structures, antibacterial activities, and interactions with DNA of two nickel complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 78-86. doi: 10.11862/CJIC.20250141
14. [14]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
15. [15]
  Peipei CUI , Yawen ZHENG , Pan LI , Peiyan GUAN , Zhaohong QIAN . Praseodymium-organic framework with 4, 4′-oxybis(benzoic acid): Rare broken layer structure, antibacterial activity, and sensing for Cd²⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1641-1649. doi: 10.11862/CJIC.20250152
16. [16]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
17. [17]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
18. [18]
  Lifang HE , Yaoze LUO , Qiying SHI , Jianxin TANG , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and properties of hydrated tricyclohexyltin theophylline-7-acetic acid complex. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 632-640. doi: 10.11862/CJIC.20250244
19. [19]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
20. [20]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(1455)
HTML views(78)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142