Citation: Siran Wang, Yinuo Wang, Yilong Zhao, Dazhen Xu. Advances in the Application and Preparation of Rhodanine and Its Derivatives[J]. University Chemistry, ;2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033 shu

Advances in the Application and Preparation of Rhodanine and Its Derivatives

National Engineering Research Center of Pesticide, College of Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: Dazhen Xu, xudazhen@nankai.edu.cn
Received Date: 4 July 2024
Revised Date: 23 October 2024

Rhodanine and its derivatives are privileged scaffolds commonly found in synthetic compounds. Molecules containing this structural motif often display remarkable biological and pharmacological activities, including antidiabetic, antibacterial, anticancer, and anti-HIV effects. Additionally, they serve as optoelectronic materials, dyes, and analytical reagents. This article provides an overview of the properties and applications of rhodanine and its derivatives, summarizes recent advancements in their preparation methods, and discusses future prospects for research in this field.
- Heterocycle,
- Biological activity,
- Carbon disulfide,
- Alkylamine,
- Thiazolidinone
1. [1]
  Nencki, M. J. Prakt. Chem. 1877, 16, 1.
2. [2]
  Aiello, D.; Barnes, M. H.; Biswas, E. E.; Biswas, S. B.; Gu, S.; Williams, J. D.; Bowlin, T. L.; Moir, D. T. Bioorg. Med. Chem. 2009, 17, 4466.
3. [3]
  Ren, Z.-L.; Yang, N.; Ji, C.; Zheng, J.; Wang, T.; Liu, Y.-Y.; Zuo, P.-P. Neuropharmacology 2015, 93, 209.
4. [4]
5. [5]
  Ohishi, Y.; Mukai, T.; Nagahara, M.; Yajima, M.; Kajikawa, N.; Miyahara, K.; Takano, T. Chem. Pharm. Bull. 1990, 38, 1911.
6. [6]
  Momose, Y.; Meguro, K.; Ikeda, H.; Hatanaka, C.; Oi, S.; Sohda, T. Chem. Pharm. Bull. 1991, 39, 1440.
7. [7]
  Terashima, H.; Hama, K.; Yamamoto, R; Tsuboshima, M.; Kikkawa, I.; Shigeta, Y. J. Pharmacol. Exp. Ther. 1984, 229, 226.
8. [8]
  Chen, Z.-H.; Zheng, C.-J.; Sun, L.-P.; Piao, H.-R. Eur. J. Med. Chem. 2010, 45, 5739.
9. [9]
  Tejchman, W.; Korona-Glowniak, I.; Malm, A.; Zylewski, M.; Suder, P. Med. Chem. Res. 2017, 26, 1316.
10. [10]
  Li, H.-Q.; Yang, J.; Ma, S.-S.; Qiao, C. H. Bioorg. Med. Chem. 2012, 20, 4194.
11. [11]
  Tihomir, T.; Nace, Z.; Veronika, R.; Andreja, K.; Didier, B.; Stanislav, G.; Danijel, K.; Lucija, P. M. Bioorg. Med. Chem. Lett. 2009, 19, 153.
12. [12]
  Nace, Z.; Tihomir, T.; Roman, S.; Veronika, R.; Andreja, K.; Delphine, P.; Didier, B.; Carlos, C. M.; Andrea, D.; Manica, M.; et al. J. Med. Chem. 2010, 53, 6584.
13. [13]
  Nace, Z.; Tihomir, T.; Roman, S.; Andreja, K.; Delphine, P.; Didier, B.; Carlos, C. M.; Andrea, D.; Manica, M. P.; Anamarija, Z.; et al. Eur. J. Med. Chem. 2011, 46, 5512.
14. [14]
  Tihomir, T.; Andreja, K.; Mihael, S.; Didier, B.; Stanislav, G. G.; Stanislav, G.; Danijel, K.; Lucija, P. M. Eur. J. Med. Chem. 2011, 46, 3964.
15. [15]
  Maga, G.; Falchi, F.; Garbelli, A.; Belfiore, A.; Witvrouw, M; Manetti, F.; Botta, M. J. Med. Chem. 2008, 51, 6635.
16. [16]
  An, Q.-S.; Wang, J.; Gao, W.; Ma. X.-L.; Hu, Z. H.; Gao, J.-H.; Xu, C.-Y.; Hao, M.-H.; Zhang, X.-L.; Yang, C.-L.; et al. Sci. Bull. 2020, 65, 538.
17. [17]
  Liu, L.; Kan, Y.-Y.; Gao, K.; Wang, J.-X.; Zhao, M.; Chen, H.; Zhao, C.-J.; Jiu, T.-G.; Jen, A. K. J.; Li, Y.-L. Adv. Mater. 2020, 32, 1907604.
18. [18]
  Hawks, S. A.; Deledalle, F.; Yao, J.-Z.; Rebois, D. G.; Li, G.; Nelson, J.; Yang, Y.; Kirchartz, T.; James, R. D. Adv. Energy Mater. 2013, 3, 1201.
19. [19]
20. [20]
21. [21]
  Lebeuf, R.; Ferezou, I.; Rossier, J.; Arseniyadis, S.; Cossy, J. Org. Lett. 2009, 11,4822.
22. [22]
23. [23]
24. [24]
25. [25]
26. [26]
27. [27]
28. [28]
29. [29]
  Julian, P. L.; Sturgis, B. M. J. Am. Chem. Soc. 1935, 57, 1126.
30. [30]
  Alizadeh, A.; Rostamnia, S.; Zohreh, N.; Hosseinpour, R. Tetrahedron Lett. 2009, 50, 1533.
31. [31]
  Attanasi, O. A.; Crescentini, L. D.; Favi, G.; Filippone, P.; Giorgi, G.; Mantellin, F.; Moscatelli, G.; Behalo, M. S. Org. Lett. 2009, 11, 2265.
32. [32]
  Sharma, A.; Pandey, S. K. Chem. Commun. 2023, 59, 1509.
33. [33]
  Lei, K.-Q.; Feng, J; Guo, Q.-L.; Xu, C.-B.; Shi, J.-G. Org. Lett. 2022, 24, 2837.
34. [34]
  Radi, M.; Botta, L.; Casaluce, G.; Bernardini, M.; Botta, M. J. Comb. Chem. 2010, 12, 200.
35. [35]
  Pan, Z.-L.; An, W.-K.; Wu, L.-L.; Fan, L.-X.; Yang, G.-Y.; Xu, G.-L. Synlett 2021, 32, 1131.
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