Citation: Liu Jingbo, Li Fengyun, Wang Yuanhong, Zhang Haoxuan, Dong Jingyue, Sun Pengwei, Li Yuxin, Li Zhengming. Synthesis, biological activities and 3D-QSAR studies of (R)-2-phenyl-4, 5-dihydrothiazole-4-carboxamide derivatives containing a sulfur ether moiety[J]. Chinese Chemical Letters, ;2019, 30(3): 668-671. doi: 10.1016/j.cclet.2018.11.001 shu

Synthesis, biological activities and 3D-QSAR studies of (R)-2-phenyl-4, 5-dihydrothiazole-4-carboxamide derivatives containing a sulfur ether moiety

a.
College of Horticulture and Landscape Architecture, Tianjin Agricultural University, Tianjin 300384, China
b.
College of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, China
c.
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin 300071, China

liyx128@nankai.edu.cn

nkzml@vip.163.com

Received Date: 23 September 2018
Revised Date: 28 October 2018
Accepted Date: 2 November 2018
Available Online: 1 March 2018

Figures(2)

A series of (R)-2-phenyl-4, 5-dihydrothiazole-4-carboxamide derivatives containing a sulfur ether moiety were synthesized and characterized on the basis of NMR and elemental analysis (EA). The crystal structure of (R)-N-(2-methyl-1-(methylthio)propan-2-yl)-2-(4-nitrophenyl)-4, 5-dihydrothiazole-4-carboxamide (13d) was determined to show R configuration. The bioasssy results indicated that most title compounds displayed good and broad spectrum antifungal activities against several phytopathogenic fungi. The structure activity relationships were discussed. Based on the antifungal activity of title compounds against Phytophthora capsici, a CoMSIA calculation was performed to establish a 3D-QSAR model, which revealed that electrostatic and hydrophobic fields were the two most significant factors for antifungal activity. According to the established 3D-QSAR model, structure optimization was carried out to find (R)-N-((R)-1-(methylthio)propan-2-yl)-2-(p-tolyl)-4, 5-dihydrothiazole-4-carboxamide (15h) with excellent activity against Phytophthora capsici, thus emerging as a new lead compound for novel antiphytopathogenic fungus agent development.
- (R)-2-Phenyl-4, 5-dihydrothiazole-4-carboxamide,
- Sulfur ether,
- Antifungal activity,
- SARs,
- CoMSIA model
1. [1]
  Y.B. Bai, A.L. Zhang, J.J. Tang, et al., J. Agric. Food Chem. 61(2013) 2789-2795. doi: 10.1021/jf3053934
2. [2]
  A. Sessitsch, B. Mitter, Microb. Biotechnol. 8(2015) 32-33. doi: 10.1111/1751-7915.12180
3. [3]
  D.W. Cai, Bull. Agric. Sci. Technol. 1(2008) 36-38.
4. [4]
  T. Mukohara, S. Nagai, H. Mukai, et al., Invest. New Drug 30(2012) 1926-1933. doi: 10.1007/s10637-011-9741-2
5. [5]
  D. Lau, Semin. Oncol. 26(1999) 12.
6. [6]
  S. Li, G.M. Li, X.H. Yang, et al., Bioorg. Med. Chem. Lett. 28(2018) 2275-2278. doi: 10.1016/j.bmcl.2018.05.035
7. [7]
  S.S. Wang, Bioorg. Med. Chem. Lett. 23(2013) 4424-4427. doi: 10.1016/j.bmcl.2013.05.057
8. [8]
  P. Buragohain, B. Saikia, N. Surineni, et al., Bioorg. Med. Chem. Lett. 24(2014) 237-239. doi: 10.1016/j.bmcl.2013.11.032
9. [9]
  F. Yi, C.H. Zou, Q.B. Hu, et al., Molecules 17(2012) 7533-7542. doi: 10.3390/molecules17067533
10. [10]
  A.M. Rimando, S.O. Duke, Natural products for pest management, in: A.M. Rimando, S.O. Duke (Eds.), Natural Products for Pest Management, American Chemical Society, Washington, DC, 2006, pp. 2-21.
11. [11]
  B.A. Song, S. Yang, L.H. Jin, et al., Environment-friendly Anti-plant Viral Agents, Chemical Industry Press, Beijing, 2009, pp. 1-305.
12. [12]
  H.Y. Sun, H. Li, J.Y. Wang, et al., Chin. Chem. Lett. 29(2018) 977-980. doi: 10.1016/j.cclet.2017.10.015
13. [13]
  R.G. Yang, Y. Guo, Y.Y. Zhang, et al., Chin. Chem. Lett. 29(2018) 995-997. doi: 10.1016/j.cclet.2017.10.018
14. [14]
  G.T. Elliot, K.F. Kelly, R.L. Bonna, et al., Cancer Chemother. Pharm. 21(1988) 233-236.
15. [15]
  K.L. Rinehart, A.L. Staley, S.R. Wilson, J. Org. Chem. 60(1995) 2786-2791. doi: 10.1021/jo00114a029
16. [16]
  V. Gududuru, E. Hurh, J.T. Dalton, et al., J. Med. Chem. 48(2005) 2584-2588. doi: 10.1021/jm049208b
17. [17]
  R.S. Guo, E.A. Kasbohm, P. Arora, et al., Endocrinology 147(2006) 4883-4892. doi: 10.1210/en.2005-1635
18. [18]
  G. Pattenden, S.T. Thom, J. Chem. Soc. Perk. Trans. 1(14) (1993) 1629-1636.
19. [19]
  A. Zamri, I.J. Schalk, F. Pattus, et al., Bioorg. Med. Chem. Lett. 13(2003) 1147-1150. doi: 10.1016/S0960-894X(03)00010-6
20. [20]
  J.B. Liu, Y.X. Li, Y.W. Chen, et al., Chin. J. Chem. 33(2015) 1269-1275. doi: 10.1002/cjoc.v33.11
21. [21]
  P. Devendar, G.F. Yang, Top. Curr. Chem. 375(2017) 1-44. doi: 10.1007/s41061-016-0088-1
22. [22]
  T.R. Fukuto, M.A.H. Fahmy, Am. Chem. Soc. 158(1981) 35-49.
23. [23]
  R.M. Hollingworth, N. Kurihara, J. Miyamoto, et al., Pure Appl. Chem. 67(1995) 1487-1532. doi: 10.1351/pac199567081487
24. [24]
  X.W. Hua, W.T. Mao, Z.J. Fan, et al., Aust. J. Chem. 67(2014) 1491-1503. doi: 10.1071/CH13701
1. [1]
  Yun-Feng Liu , Hui-Fang Du , Ya-Hui Zhang , Zhi-Qin Liu , Xiao-Qian Qi , Du-Qiang Luo , Fei Cao . Chaeglobol A, an unusual octocyclic sterol with antifungal activity from the marine-derived fungus Chaetomium globosum HBU-45. Chinese Chemical Letters, 2025, 36(3): 109858-. doi: 10.1016/j.cclet.2024.109858
2. [2]
  Yunxin Li , Jinghui Zhang , Jisen Chen , Feng Zhu , Zhiqiang Liu , Peng Bao , Wei Shen , Sheng Tang . Detection of SARS-CoV-2 based on artificial intelligence-assisted smartphone: A review. Chinese Chemical Letters, 2024, 35(7): 109220-. doi: 10.1016/j.cclet.2023.109220
3. [3]
  Gengchen Guo , Tianyu Zhao , Ruichang Sun , Mingzhe Song , Hongyu Liu , Sen Wang , Jingwen Li , Jingbin Zeng . Au-Fe₃O₄ dumbbell-like nanoparticles based lateral flow immunoassay for colorimetric and photothermal dual-mode detection of SARS-CoV-2 spike protein. Chinese Chemical Letters, 2024, 35(6): 109198-. doi: 10.1016/j.cclet.2023.109198
4. [4]
  Xiaoli Deng , Xiangchao Lu , Yang Cao , Qianjin Chen . Electrochemical imaging uncovers the heterogeneity of HER activity by sulfur vacancies in molybdenum disulfide monolayer. Chinese Chemical Letters, 2025, 36(3): 110379-. doi: 10.1016/j.cclet.2024.110379
5. [5]
  Xing Xiao , Yunling Jia , Wanyu Hong , Yuqing He , Yanjun Wang , Lizhi Zhao , Huiqin An , Zhen Yin . Sulfur-defective ZnIn2S4 nanosheets decorated by TiO2 nanosheets with exposed {001} facets to accelerate charge transfer for efficient photocatalytic hydrogen evolution. Chinese Journal of Structural Chemistry, 2024, 43(12): 100474-100474. doi: 10.1016/j.cjsc.2024.100474
6. [6]
  Bingwei Wang , Yihong Ding , Xiao Tian . Benchmarking model chemistry composite calculations for vertical ionization potential of molecular systems. Chinese Chemical Letters, 2025, 36(2): 109721-. doi: 10.1016/j.cclet.2024.109721
7. [7]
  Chen Chen , Jinzhou Zheng , Chaoqin Chu , Qinkun Xiao , Chaozheng He , Xi Fu . An effective method for generating crystal structures based on the variational autoencoder and the diffusion model. Chinese Chemical Letters, 2025, 36(4): 109739-. doi: 10.1016/j.cclet.2024.109739
8. [8]
  Hailang Deng , Abebe Reda Woldu , Abdul Qayum , Zanling Huang , Weiwei Zhu , Xiang Peng , Paul K. Chu , Liangsheng Hu . Killing two birds with one stone: Enhancing the photoelectrochemical water splitting activity and stability of BiVO₄ by Fe ions association. Chinese Chemical Letters, 2024, 35(12): 109892-. doi: 10.1016/j.cclet.2024.109892
9. [9]
  Xiao Zhu , Yanbing Mo , Jiawei Chen , Gaopan Liu , Yonggang Wang , Xiaoli Dong . A weakly-solvated ether-based electrolyte for fast-charging graphite anode. Chinese Chemical Letters, 2024, 35(8): 109146-. doi: 10.1016/j.cclet.2023.109146
10. [10]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
11. [11]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
12. [12]
  Ruiying Liu , Li Zhao , Baishan Liu , Jiayuan Yu , Yujie Wang , Wanqiang Yu , Di Xin , Chaoqiong Fang , Xuchuan Jiang , Riming Hu , Hong Liu , Weijia Zhou . Modulating pollutant adsorption and peroxymonosulfate activation sites on Co3O4@N,O doped-carbon shell for boosting catalytic degradation activity. Chinese Journal of Structural Chemistry, 2024, 43(8): 100332-100332. doi: 10.1016/j.cjsc.2024.100332
13. [13]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
14. [14]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
15. [15]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
16. [16]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
17. [17]
  Tao Wei , Jiahao Lu , Pan Zhang , Qi Zhang , Guang Yang , Ruizhi Yang , Daifen Chen , Qian Wang , Yongfu Tang . An intermittent lithium deposition model based on bimetallic MOFs derivatives for dendrite-free lithium anode with ultrahigh areal capacity. Chinese Chemical Letters, 2024, 35(8): 109122-. doi: 10.1016/j.cclet.2023.109122
18. [18]
  Haodong Wang , Xiaoxu Lai , Chi Chen , Pei Shi , Houzhao Wan , Hao Wang , Xingguang Chen , Dan Sun . Novel 2D bifunctional layered rare-earth hydroxides@GO catalyst as a functional interlayer for improved liquid-solid conversion of polysulfides in lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(5): 108473-. doi: 10.1016/j.cclet.2023.108473
19. [19]
  Simin Wei , Yaqing Yang , Junjie Li , Jialin Wang , Jinlu Tang , Ningning Wang , Zhaohui Li . The Mn/Yb/Er triple-doped CeO₂ nanozyme with enhanced oxidase-like activity for highly sensitive ratiometric detection of nitrite. Chinese Chemical Letters, 2024, 35(6): 109114-. doi: 10.1016/j.cclet.2023.109114
20. [20]
  Peng Zhang , Yitao Yang , Tian Qin , Xueqiu Wu , Yuechang Wei , Jing Xiong , Xi Liu , Yu Wang , Zhen Zhao , Jinqing Jiao , Liwei Chen . Interface engineering of Pt/CeO₂-{100} catalysts for enhancing catalytic activity in auto-exhaust carbon particles oxidation. Chinese Chemical Letters, 2025, 36(2): 110396-. doi: 10.1016/j.cclet.2024.110396

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(704)
HTML views(60)

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