Design, Synthesis and Antioxidant Application of Camphorsulfonic Acid Thiazolylhydrazone Derivatives

doi:10.6023/cjoc201901053

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2616-2624.DOI: 10.6023/cjoc201901053 Previous Articles Next Articles

ARTICLE

樟脑磺酸噻唑腙类化合物的设计、合成及抗氧化应用

张强健^a, 王芸芸^a, 赵雨珣^a, 马崇慧^a, 徐徐^a,c, 谷文^a,c, 杨益琴^b,c, 王石发^a,c

a 南京林业大学化学工程学院南京 210037;
b 南京林业大学轻工与食品学院南京 210037;
c 南京林业大学林业资源高效加工利用协同创新中心南京 210037

收稿日期:2019-01-30 修回日期:2019-03-17 发布日期:2019-04-11
通讯作者: 王石发 E-mail:wangshifa65@163.com
基金资助:
国家自然科学基金（No.31470592）资助项目.

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

Received:2019-01-30 Revised:2019-03-17 Published:2019-04-11
Contact: 10.6023/cjoc201901053 E-mail:wangshifa65@163.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31470592).

1. Design, Synthesis and Antioxidant Application of Camphorsulfonic Acid Thiazolylhydrazone Derivatives.PDF(3449KB)

Abstract

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.

Key words: camphorsulfonic acid, thiazolylhydrazone, antioxidant activity

Cite this article

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]. Chin. J. Org. Chem., 2019, 39(9): 2616-2624.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Limtrakul, P.; Yodkeeree, S.; Thippraphan, P. BMC Com-plementary Altern. Med. 2016, 16, 497.
[2] Gragnani, A.; Cornick, S.; Chominski, V. Adv. Aging Res. 2014, 3, 265.
[3] Pedrosa, T.; Barros, A.; Nogueira, J. Arch. Dermatol. Res. 2016, 308, 643.
[4] Delalle-Lozica, N. Acta Clin. Croat. 2010, 49, 529.
[5] Jae, Y. L.; Young-Rak, C.; Ju, H. P. Toxicol. Rep. 2019, 6, 10.
[6] Limtrakul, P.; Yodkeeree, S.; Thippraphan, P. BMC Com-plementary Altern. Med. 2016, 16, 497.
[7] Alfredo, G.; Sarita, M. C.; Verônica, C. Adv. Aging Res. 2014, 3, 265.
[8] Laguerre, M.; Lecomte, J.; Villeneuve, P. Prog. Lipid Res. 2007, 46, 244.
[9] Amorati, R.; Foti, M.; Valgimigli, L. J. Agric. Food Chem. 2013, 61, 10835.
[10] Liu, Y.; Huang, G.; Hu, J. Int. J. Biol. Macromol. 2018, 111, 1304.
[11] Didem, ?.; Suat, S.; Burak, B. Bioorg. Chem. 2018, 81, 168.
[12] Li, X.; Huang, J.; Wang, Z. Sep. Purif. Technol. 2014, 124, 201.
[13] Adelakun, O.; Kudanga, T.; Parker, A. J. Mol. Catal. B:Enzym. 2012, 74, 29.
[14] Adom, K.; Liu, R. J. Agric. Food Chem. 2005, 53, 6572.
[15] Erzsébet, I.; Amir, M.; Vered, M. Free Radical Biol. Med. 2019, 131, 1.
[16] Jae, Y.; Young, R.; Ju, H. Toxicol. Rep. 2019, 6, 10.
[17] Olanow, C. Trends Neurosci. 1993, 16, 439.
[18] Bennett, S.; Grant, M.; Aldreda, S. J. Alzheimer's Dis. 2009, 17, 245.
[19] Rietveld, I.; Barrio, M.; Veglio, N. Thermochim. Acta 2010, 511, 43.
[20] Andersson, O.; Ross, R.; Jezowski, A. Mol. Phys. 1990, 70, 1065.
[21] Kisiel, Z.; Desyatnyk, O.; Bia?kowska-Jaworska, E. Phys. Chem. Chem. Phys. 2003, 5, 820.
[22] Hargrave, K.; Hess, F.; Oliver, J. J. Med. Chem. 1983, 26, 1158.
[23] Patt, W.; Hamilton, H.; Taylor, M. J. Med. Chem. 1992, 35, 2562.
[24] Kamble, R.; Meshram, R.; Hese, S. Comput. Biol. Chem. 2016, 61, 86.
[25] Jaen, J.; Wise, L.; Caprathe, B. J. Med. Chem. 1990, 33, 311.
[26] Mohammad, H.; Reddy, P.; Monteleone, D. Eur. J. Med. Chem. 2015, 94, 306.
[27] Ergenç, N.; Çapan, G.; Günay, N. Arch. Pharm. (Weinheim, Ger.) 1999, 332, 343.
[28] Bell, F.; Cantrell, A.; Hoegberg, M. J. Med. Chem. 1995, 38, 4929.
[29] Badorc, A.; Bordes, M.; Cointet, P. Med. Chem. 1997, 40, 3393.
[30] Khan, K.; Qurban, S.; Salar, U. Bioorg. Chem. 2016, 68, 245.
[31] Wang, G.; Peng, Z.; Gong, Z. Bioorg. Chem. 2018, 78, 195.
[32] Paudel, Y. N.; Ali, M. R.; Shah, S. Biomed. Pharmacother. 2017, 89, 651.
[33] Rui, J.; Zhang, Q.; Wang, X. Chin. J. Org. Chem. 2017, 37, 218(in Chinese). (芮坚, 张齐, 王欣, 有机化学, 2017, 37, 218.)
[34] Sun, N.; Wang, X.; Ding, Z. Chin. J. Org. Chem. 2016, 36, 2489. (in Chinese). (孙楠, 王欣, 丁志彬, 有机化学, 2016, 36, 2489.)
[35] Wang, Y.; Gu, W.; Shan, Y. Bioorg. Med. Chem. Lett. 2017, 27, 2360.
[36] Yang, J.; Xu, X.; Rui, J. Spectrochim. Acta, Part A 2017, 183, 60.
[37] Yang, J.; Xu, H.; Xu, X. Dyes Pigm. 2016, 128, 75.
[38] Vinícius, G. M.; Marina, F. R.; Thales, K. J. Mol. Graphics Modell. 2019, 86, 106.

樟脑磺酸噻唑腙类化合物的设计、合成及抗氧化应用

Design, Synthesis and Antioxidant Application of Camphorsulfonic Acid Thiazolylhydrazone Derivatives

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 4

Recommended Articles

Metrics

Comments

[1]	Ting Zhao, Xuhua Nong, Jiali Wang, Kuanyu Xu, Minmin Tang, Jiling Yi, Changri Han, Guangying Chen. Lignanolides with Antioxidant Activity from the Stems of Dracaena angustifolia [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2968-2972.
[2]	Wang Bin, Zeng Weinv, Li Gaoyu, Xiao Mei, Wei Fangfang, Luo Youping, Niu Zhigang, Huang Guolei, Zheng Caijuan. Three New Secondary Metabolites from the Mangrove-Derived Fungus Daldinia eschscholtzii HJ004 [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 332-337.
[3]	Jin Cai, Xuhua Nong, Bin Wang, Weinü Zeng, Guolei Huang, Ziyi Zhang, Caijuan Zheng. Three New Polyketides from the Culture of Mangrove-Derived FungusEupenicilliumsp. HJ002 [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2905-2909.
[4]	Zhang Qiangjian, Wang Yunyun, Zhao Yuxun, Ma Chonghui, Yang Yiqing, Xu Xu, Gu Wen, Wang Shifa. Synthesis and α-Amylase Inhibitory Potential and Molecular Docking Study of Nopinone-Based Thiazolylhydrazone Derivatives [J]. Chin. J. Org. Chem., 2019, 39(5): 1372-1382.