Citation: Zhang Qiangjian, Wang Yunyun, Zhao Yuxun, Ma Chonghui, Xu Xu, Gu Wen, Yang Yiqing, Wang Shifa. Design, Synthesis and Antioxidant Application of Camphorsulfonic Acid Thiazolylhydrazone Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(9): 2616-2624. doi: 10.6023/cjoc201901053 shu

Design, Synthesis and Antioxidant Application of Camphorsulfonic Acid Thiazolylhydrazone Derivatives

Zhang Qiangjian ^a ,
Wang Yunyun ^a ,
Zhao Yuxun ^a ,
Ma Chonghui ^a ,
Xu Xu ^a,c ,
Gu Wen ^a,c ,
Yang Yiqing ^b,c ,
Wang Shifa ^a,c,,

a.
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037
b.
College of Light Industry and Food, Nanjing Forestry University, Nanjing 210037
c.
Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037

Corresponding author: Wang Shifa, wangshifa65@163.com
Received Date: 30 January 2019
Revised Date: 17 March 2019
Available Online: 11 September 2019
Fund Project: the National Natural Science Foundation of China 31470592Project supported by the National Natural Science Foundation of China (No. 31470592)

Figures(4)

A series of camphorsulfonic acid thiazolylhydrazone derivatives were synthesized by using camphorsulfonic acid derivated from natural camphor as the starting material in three steps, including condensation with aminothiourea and cyclization with bromoacetophenone. Their structures were characterized by ¹H NMR, ¹³C NMR and HR-MS, and their antioxidant activities were also investigated. The results showed that these compounds had good antioxidant activities compared with the positive control trolox. Among of them, (2-(2-(4-(4-cyanophenyl)thiazol-2-yl)indenyl)-7, 7-dimethylbicyclo-[2.2.1]hept-1-yl)methanesulfonic acid (Q19) exhibited the relatively strong 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity with IC₅₀ value of 176 μmol/L, (2-(2-(4-(4-fluorophenyl)thiazol-2-yl)hydrazino)-7, 7-dimethylbicyclo-[2.2.1]hept-1-yl)methanesulfonic acid (Q3) exhibited the relatively strong diammonium 2, 2'-azino-bis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) radical scavenging activity with IC₅₀ value of 20.6 μmol/L, (E)-(7, 7-dimethyl-2-(2-(4-(3-methyl)-thiazol-2-yl)indenyl)bicyclo[2.2.1]hept-1-yl)-sulfonic acid (Q8) exhibited the strong hydroxyl radical scavenging activity with scavenge rate 66.2%, (2-(2-(4-(4-biphenyl)thiazol-2-yl)indenyl)-7, 7-dimethylbicyclo[2.2.1]hept-1-yl)methane-sulfonic acid (Q20) exhibited the relatively strong superoxide radical scavenging activity with IC₅₀ value of 20.7 μmol/L. Compared with the positive control kojic acid, (2-(2-(4-(2-hydroxyphenyl)thiazol-2-yl)arylene)-7, 7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonic acid (Q16) exhibited remarkable tyrosinase inhibitory activity with IC₅₀ value of 154.9 μmol/L. It was known from the structure-activity relationship that the structure of R gave great influence on the activities of thiazolylhydrazone derivatives.
- camphorsulfonic acid,
- thiazolylhydrazone,
- antioxidant activity
1. [1]
  Limtrakul, P.; Yodkeeree, S.; Thippraphan, P. BMC Complementary Altern. Med. 2016, 16, 497. doi: 10.1186/s12906-016-1484-3
2. [2]
  Gragnani, A.; Cornick, S.; Chominski, V. Adv. Aging Res. 2014, 3, 265. doi: 10.4236/aar.2014.34036
3. [3]
  Pedrosa, T.; Barros, A.; Nogueira, J. Arch. Dermatol. Res. 2016, 308, 643. doi: 10.1007/s00403-016-1685-0
4. [4]
  Delalle-Lozica, N. Acta Clin. Croat. 2010, 49, 529.
5. [5]
  Jae, Y. L.; Young-Rak, C.; Ju, H. P. Toxicol. Rep. 2019, 6, 10. doi: 10.1016/j.toxrep.2018.11.005
6. [6]
  Limtrakul, P.; Yodkeeree, S.; Thippraphan, P. BMC Complementary Altern. Med. 2016, 16, 497. doi: 10.1186/s12906-016-1484-3
7. [7]
  Alfredo, G.; Sarita, M. C.; Verônica, C. Adv. Aging Res. 2014, 3, 265. doi: 10.4236/aar.2014.34036
8. [8]
  Laguerre, M.; Lecomte, J.; Villeneuve, P. Prog. Lipid Res. 2007, 46, 244. doi: 10.1016/j.plipres.2007.05.002
9. [9]
  Amorati, R.; Foti, M.; Valgimigli, L. J. Agric. Food Chem. 2013, 61, 10835. doi: 10.1021/jf403496k
10. [10]
  Liu, Y.; Huang, G.; Hu, J. Int. J. Biol. Macromol. 2018, 111, 1304. doi: 10.1016/j.ijbiomac.2018.01.088
11. [11]
  Didem, Ş.; Suat, S.; Burak, B. Bioorg. Chem. 2018, 81, 168. doi: 10.1016/j.bioorg.2018.08.020
12. [12]
  Li, X.; Huang, J.; Wang, Z. Sep. Purif. Technol. 2014, 124, 201. doi: 10.1016/j.seppur.2014.01.030
13. [13]
  Adelakun, O.; Kudanga, T.; Parker, A. J. Mol. Catal. B: Enzym. 2012, 74, 29. doi: 10.1016/j.molcatb.2011.08.010
14. [14]
  Adom, K.; Liu, R. J. Agric. Food Chem. 2005, 53, 6572. doi: 10.1021/jf048318o
15. [15]
  Erzsébet, I.; Amir, M.; Vered, M. Free Radical Biol. Med. 2019, 131, 1. doi: 10.1016/j.freeradbiomed.2018.11.015
16. [16]
  Jae, Y.; Young, R.; Ju, H. Toxicol. Rep. 2019, 6, 10. doi: 10.1016/j.toxrep.2018.11.005
17. [17]
  Olanow, C. Trends Neurosci. 1993, 16, 439. doi: 10.1016/0166-2236(93)90070-3
18. [18]
  Bennett, S.; Grant, M.; Aldreda, S. J. Alzheimer's Dis. 2009, 17, 245.
19. [19]
  Rietveld, I.; Barrio, M.; Veglio, N. Thermochim. Acta 2010, 511, 43. doi: 10.1016/j.tca.2010.07.023
20. [20]
  Andersson, O.; Ross, R.; Jezowski, A. Mol. Phys. 1990, 70, 1065. doi: 10.1080/00268979000101531
21. [21]
  Kisiel, Z.; Desyatnyk, O.; Białkowska-Jaworska, E. Phys. Chem. Chem. Phys. 2003, 5, 820. doi: 10.1039/b212029a
22. [22]
  Hargrave, K.; Hess, F.; Oliver, J. J. Med. Chem. 1983, 26, 1158. doi: 10.1021/jm00362a014
23. [23]
  Patt, W.; Hamilton, H.; Taylor, M. J. Med. Chem. 1992, 35, 2562. doi: 10.1021/jm00092a006
24. [24]
  Kamble, R.; Meshram, R.; Hese, S. Comput. Biol. Chem. 2016, 61, 86. doi: 10.1016/j.compbiolchem.2016.01.007
25. [25]
  Jaen, J.; Wise, L.; Caprathe, B. J. Med. Chem. 1990, 33, 311. doi: 10.1021/jm00163a051
26. [26]
  Mohammad, H.; Reddy, P.; Monteleone, D. Eur. J. Med. Chem. 2015, 94, 306. doi: 10.1016/j.ejmech.2015.03.015
27. [27]
  Ergenç, N.; Çapan, G.; Günay, N. Arch. Pharm. (Weinheim, Ger.) 1999, 332, 343. doi: 10.1002/(SICI)1521-4184(199910)332:10<343::AID-ARDP343>3.0.CO;2-0
28. [28]
  Bell, F.; Cantrell, A.; Hoegberg, M. J. Med. Chem. 1995, 38, 4929. doi: 10.1021/jm00025a010
29. [29]
  Badorc, A.; Bordes, M.; Cointet, P. Med. Chem. 1997, 40, 3393. doi: 10.1021/jm970240y
30. [30]
  Khan, K.; Qurban, S.; Salar, U. Bioorg. Chem. 2016, 68, 245. doi: 10.1016/j.bioorg.2016.08.010
31. [31]
  Wang, G.; Peng, Z.; Gong, Z. Bioorg. Chem. 2018, 78, 195. doi: 10.1016/j.bioorg.2018.03.015
32. [32]
  Paudel, Y. N.; Ali, M. R.; Shah, S. Biomed. Pharmacother. 2017, 89, 651. doi: 10.1016/j.biopha.2017.02.043
33. [33]
  Rui, J.; Zhang, Q.; Wang, X. Chin. J. Org. Chem. 2017, 37, 218 (in Chinese).
34. [34]
  Sun, N.; Wang, X.; Ding, Z. Chin. J. Org. Chem. 2016, 36, 2489. (in Chinese).
35. [35]
  Wang, Y.; Gu, W.; Shan, Y. Bioorg. Med. Chem. Lett. 2017, 27, 2360. doi: 10.1016/j.bmcl.2017.04.024
36. [36]
  Yang, J.; Xu, X.; Rui, J. Spectrochim. Acta, Part A 2017, 183, 60. doi: 10.1016/j.saa.2017.04.054
37. [37]
  Yang, J.; Xu, H.; Xu, X. Dyes Pigm. 2016, 128, 75. doi: 10.1016/j.dyepig.2016.01.016
38. [38]
  Vinícius, G. M.; Marina, F. R.; Thales, K. J. Mol. Graphics Modell. 2019, 86, 106. doi: 10.1016/j.jmgm.2018.10.007
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