Citation: Lin Guishan, Zhang Rui, Duan Wengui, He Yun, Cen Bo, Lu Shunzhong. Syntheses and Antifungal Activities of Verbenone-Based Thiazole-hydrazone Compounds[J]. Chemistry, ;2020, 83(2): 132-138. shu

Syntheses and Antifungal Activities of Verbenone-Based Thiazole-hydrazone Compounds

Lin Guishan ¹ ,
Zhang Rui ¹ ,
Duan Wengui ^1,, ,
He Yun ¹ ,
Cen Bo ¹ ,
Lu Shunzhong ²

1.
School of Chemistry and Chemical Engineering, Guangxi University, Nanning, 530004
2.
Guangxi Academy of Forestry, Nanning, 530002

Corresponding author: Duan Wengui, wgduan@gxu.edu.cn
Received Date: 4 September 2019
Accepted Date: 25 September 2019

Figures(3)

In this paper, nine verbenone-based thiazole-hydrazone compounds 4a~4i, including three pairs of E-Z isomers and three E-products were synthesized. All the target compounds were characterized by FTIR, ¹H NMR, ¹³C NMR, ESI-MS, and NOESY, and their antifungal activities were evaluated as well. The results showed that, at 50mg/L, compounds 4a~4i showed certain antifungal activities against Physalospora piricola, Gibberella zeae, Fusarium oxysporum f. cucumerinum, Cercospora arachidicola, Alternaria solani, Rhizoctonia solani, Helminthosporium maydis, and Colleetotrichum lagenarium. It was found that the E-Z isomers exhibited obvious difference in antifungal activity against some pathogens. For example, the inhibition rate of (Z)-verbenone-based p-cyanophenyl thiazole-hydrazone (4f) against Gibberella zeae was 6 times that of (E)-verbenone-based p-cyanophenyl thiazole-hydrazone (4e). The frontier molecular orbitals of compounds 4e and 4f were calculated by Gaussian 09 software.
- Verbenone,
- Thiazole-hydrazone,
- Antifungal activity
1. [1]
  Allal B A, Firdoussi L E, Allal S, et al. J. Mol. Catal. A, 2003, 200(1/2): 177~184.
2. [2]
3. [3]
  Borden J H, Chong L J, Earle T J, et al. Forest. Chron., 2003, 79(3): 685~691.
4. [4]
  Shore T L, Safranyak L, Lindgren B S. J. Chem. Ecol., 1992, 18(4): 533~541.
5. [5]
  Gatilov Y V, Basalaeva L V, Kozlov N G, et al. Chem. Heterocycl. Com., 1995, 31(5): 625~628.
6. [6]
  Ju C, Song S, Hwang S, et al. Bioorg. Med. Chem. Lett., 2013, 23(19): 5421~5425.
7. [7]
  Pawar C D, Sarkate A P, Karnik K S, et al. Bioorg. Med. Chem. Lett., 2016, 26(15): 3525~3528.
8. [8]
  Grozav A, Porumb I D, Gaina L I, et al. Molecules, 2017, 22(2): 260~271.
9. [9]
10. [10]
  Mo W Y, Shi Y X, He J B, et al. J. Heterocycl. Chem., 2016, 53(1): 183~187.
11. [11]
  Irahim H S, Abou-Seri S M, Ismail N S M, et al. Eur. J. Med. Chem., 2016, 108: 415~422.
12. [12]
  Senkardes S, Kaushik-Basu N, Durmaz I, et al. Eur. J. Med. Chem., 2016, 108: 301~308.
13. [13]
  Rawat P, Singh R N, Niranjan P, et al. J. Mol. Struct., 2017, 1149: 539~548.
14. [14]
  Can N O, Osmaniye D, Levent S, et al. Molecules, 2017, 22(8): 1381~1399.
15. [15]
16. [16]
  Lin G S, Bai X, Duan W G, et al. ACS Sustain. Chem. Eng., 2019, 7(8): 7862~7868.
17. [17]
18. [18]
  Hu Q, Lin G S, Duan W G, et al. Molecules, 2017, 22(10): 1678~1694.
19. [19]
  Chen N Y, Duan W G, Lin G S, et al. Mol. Divers., 2016, 20(4): 897~905.
20. [20]
  Lin G S, Ma C H, Duan W G, et al. Holzforschung, 2014, 68(1): 75~83.
21. [21]
22. [22]
  Monte C D, Carradori S, Secci D, et al. Eur. J. Med. Chem., 2015, 105: 245~262.
23. [23]
  Su N N, Li Y, Yu S J, et al. Res. Chem. Intermediat., 2013, 39(2): 759~766.
24. [24]
  Wang B L, Shi Y X, Zhang S J, et al. Eur. J. Med. Chem., 2016, 117: 167~178.
25. [25]
  Frisch M J, Trucks G W, Schlegel H B et al. Gaussian 09, Gaussian, Inc.: Wallingford, CT, 2009.
26. [26]
  Dennington R, Keith T, Millam J. GaussView version 5, Semichem, Inc.: Shawnee Mission, KS, 2009.
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]
  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
3. [3]
  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
4. [4]
  Lijuan Wang , Yuping Ning , Jian Li , Sha Luo , Xiongfei Luo , Ruiwen Wang . Enhancing the Advanced Nature of Natural Product Chemistry Laboratory Courses with New Research Findings: A Case Study of the Application of Berberine Hydrochloride in Photodynamic Antimicrobial Films. University Chemistry, 2024, 39(11): 241-250. doi: 10.12461/PKU.DXHX202403017
5. [5]
  Jingjie Tang , Luying Xie , Jiayu Liu , Shangyu Shi , Xinyu Sun , Jiayang Lin , Qikun Yang , Chuan'ang Yu , Zecheng Wang , Yingying Wang , Zengyang Xie . Efficient Rapid Synthesis and Antibacterial Activities of Tosylhydrazones: A Recommended Innovative Chemistry Experiment for Undergraduate Medical University. University Chemistry, 2024, 39(3): 316-326. doi: 10.3866/PKU.DXHX202309091
6. [6]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
7. [7]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
8. [8]
  Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133
9. [9]
  Xinyu ZENG , Guhua TANG , Jianming OUYANG . Inhibitory effect of Desmodium styracifolium polysaccharides with different content of carboxyl groups on the growth, aggregation and cell adhesion of calcium oxalate crystals. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1563-1576. doi: 10.11862/CJIC.20230374
10. [10]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
11. [11]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
12. [12]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
13. [13]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
14. [14]
  Yukai Jiang , Yihan Wang , Yunkai Zhang , Yunping Wei , Ying Ma , Na Du . Characterization and Phase Diagram of Surfactant Lyotropic Liquid Crystal. University Chemistry, 2024, 39(4): 114-118. doi: 10.3866/PKU.DXHX202309033
15. [15]
  Jiayu Gu , Siqi Wang , Jun Ling . Kinetics of Living Copolymerization: A Brief Discussion. University Chemistry, 2025, 40(4): 100-107. doi: 10.12461/PKU.DXHX202406012
16. [16]
  Zhiyang Li , Hui Deng , Xinqi Cai , Zhuo Chen . Magnetic Core/Shell-Capsules Locally Neutralize Gastric Acid for Efficient Delivery of Active Probiotics. Acta Physico-Chimica Sinica, 2024, 40(7): 2306051-0. doi: 10.3866/PKU.WHXB202306051
17. [17]
  Ruiqin Feng , Ye Fan , Yun Fang , Yongmei Xia . Strategy for Regulating Surface Protrusion of Gold Nanoflowers and Their Surface-Enhanced Raman Scattering. Acta Physico-Chimica Sinica, 2024, 40(4): 2304020-0. doi: 10.3866/PKU.WHXB202304020
18. [18]
  Yunting Shang , Yue Dai , Jianxin Zhang , Nan Zhu , Yan Su . Something about RGO (Reduced Graphene Oxide). University Chemistry, 2024, 39(9): 273-278. doi: 10.3866/PKU.DXHX202306050
19. [19]
  Anbang Du , Yuanfan Wang , Zhihong Wei , Dongxu Zhang , Li Li , Weiqing Yang , Qianlu Sun , Lili Zhao , Weigao Xu , Yuxi Tian . Photothermal Microscopy of Graphene Flakes with Different Thicknesses. Acta Physico-Chimica Sinica, 2024, 40(5): 2304027-0. doi: 10.3866/PKU.WHXB202304027
20. [20]
  Zhihuan XU , Qing KANG , Yuzhen LONG , Qian YUAN , Cidong LIU , Xin LI , Genghuai TANG , Yuqing LIAO . Effect of graphene oxide concentration on the electrochemical properties of reduced graphene oxide/ZnS. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1329-1336. doi: 10.11862/CJIC.20230447

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(509)
HTML views(159)

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