Synthesis and α-Amylase Inhibitory Potential and Molecular Docking Study of Nopinone-Based Thiazolylhydrazone Derivatives

doi:10.6023/cjoc201812032

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (5): 1372-1382.DOI: 10.6023/cjoc201812032 Previous Articles Next Articles

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诺蒎酮基噻唑腙类化合物的合成及对α-淀粉酶的抑制活性

张强健^a, 王芸芸^a, 赵雨珣^a, 马崇慧^a, 杨益琴^b,c, 徐徐^a,c, 谷文^a,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:2018-12-19 修回日期:2019-01-14 发布日期:2019-02-19
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.

Synthesis and α-Amylase Inhibitory Potential and Molecular Docking Study of Nopinone-Based Thiazolylhydrazone Derivatives

Zhang Qiangjian^a, Wang Yunyun^a, Zhao Yuxun^a, Ma Chonghui^a, Yang Yiqing^b,c, Xu Xu^a,c, Gu Wen^a,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:2018-12-19 Revised:2019-01-14 Published:2019-02-19
Contact: 10.6023/cjoc201812032 E-mail:wangshifa65@163.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31470592).

A series of nopinone-based thiazolyhydrazone derivatives were synthesized by using nopinone derivated from natural β-pinene as the starting material in three steps, including aldol reaction with aromatic aldehydes, condensation with aminothiourea, and cyclization with bromoacetophenone. The structures of synthesized compounds were characterized by ¹H NMR, ¹³C NMR and HRMS. α-Amylase inhibitory activities of these compounds were also investigated. The results showed that 6 compounds among them had good inhibitory activities compared with the positive control acarbose. Especially, 4-(2-(2-(6,6-dimethyl-3-(4-methylbenzylidene))bicyclo[3.1.1]heptane-2-ylidene)indolyl-4-thiazol-4-yl)phenol (SZ14) exhibited remarkable α-amylase inhibitory activity with IC₅₀ value of 4.11 μmol/L. From the structure-activity relationship, the structure of R² gave great influence on the activities of thiazolyhydrazone derivatives. The kinetic inhibition study revealed that those 6 compounds were the noncompetitive inhibitor against α-amylase. It was used for molecular docking study to find out binding affinities for thiazolylhydrazone derivatives, and the binding mode of compound SZ14 with α-amylase was primarily investigated with molecular docking method.

Key words: nopinone, thiazolylhydrazone, α-amylase inhibitor, molecular docking

Cite this article

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.

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References

[1] Rathmann, W; Giani, G. Diabetes Care 2004, 27, 1047.
[2] Gupta, Y.; Tandon, N. Nat. Med. J. India 2016, 29, 189.
[3] Liu, T.; Song, L.; Wang, H. J. Agric. Food Chem. 2011, 59, 9756.
[4] Mellor, D. D.; Sathyapalan, T.; Kilpatrick, E. S. J. Agric. Food Chem. 2015, 63, 9910.
[5] Murotomi, K.; Umeno, A.; Yasunaga, M. J. Agric. Food Chem. 2015, 63, 6715.
[6] Alberti, G.; Zimmet, P.; Shaw, J. Diabetes Care 2004, 27, 1798.
[7] Fowler, M. J. Clin. Diabetes 2008, 26, 77.
[8] Jarald, E.; Joshi, S. B.; Jain, D. C. Iran. J. Pharmacol. Ther. 2008, 7, 97.
[9] Bhandari, M. R.; Jong-Anurakkun, N.; Hong, G. Food Chem. 2008, 106, 247.
[10] Camargo, A. C.; Regitano-d'Arce, M. A. B.; Biasoto, A. C. T. Food Chem. 2016, 212, 395.
[11] Zhang, Y.; Wong, A. I. C.; Wu, J. J. Funct. Foods 2016, 25, 568.
[12] Ma, Y. Y.; Zhao, D. G.; Zhou, A. Y. J. Agric. Food Chem. 2015, 63, 8162.
[13] Martinez-Gonzalez, A. I.; Díaz-Sánchez, Á. G. Spectrochim. Acta, Part A 2019, 206, 437.
[14] Taha, M.; Syukri, B. M.; Hadiani, I, N. Bioorg. Chem. 2018, 80, 36.
[15] Yousuf, S.; Khan, K. M.; Salar, U. Eur. J. Med. Chem. 2018, 159, 47.
[16] Figueiredo-González, M.; Reboredo-Rodríguez, P.; González-Bar- reiro, C. Food Res. Int. 2019, 116, 447.
[17] Sun, L.; Chen, W.; Meng, Y. Food Chem. 2016, 208, 51.
[18] Hargrave, K. D.; Hess, F. K.; Oliver, J. T. J. Med. Chem. 1983, 26, 1158.
[19] Patt, W. C.; Hamilton, H. W.; Taylor, M. D. J. Med. Chem. 1992, 35, 2562.
[20] Kamble, R. D.; Meshram, R. J.; Hese, S. V. Comput. Biol. Chem. 2016, 61, 86.
[21] Jaen, J. C.; Wise, L. D.; Caprathe, B. W. J. Med. Chem. 1990, 33, 311.
[22] Mohammad, H.; Reddy, P. V. N.; Monteleone, D. Eur. J. Med. Chem. 2015, 94, 306.
[23] Ergenç, N.; Çapan, G.; Günay, N. S. Arch. Pharm. 1999, 332, 343.
[24] Bell, F. W.; Cantrell, A. S.; Hoegberg, M. J. Med. Chem. 1995, 38, 4929.
[25] Badorc, A.; Bordes, M. F.; Cointet, P. J. Med. Chem. 1997, 40, 3393.
[26] Khan, K. M.; Qurban, S.; Salar, U. Bioorg. Chem. 2016, 68, 245.
[27] Wang, G.; Peng, Z.; Gong, Z. Bioorg. Chem. 2018, 78, 195.
[28] Paudel, Y. N.; Ali, M. R.; Shah, S. Biomed. Pharmacother. 2017, 89, 651.
[29] 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.)
[30] 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.)
[31] Wang, Y.; Gu, W.; Shan, Y. Bioorg. Med. Chem. Lett. 2017, 27, 2360.
[32] Yang, J.; Xu, X.; Rui, J. Spectrochim. Acta, Part A 2017, 183, 60.
[33] Yang, J.; Xu, H.; Xu, X. Dyes Pigm. 2016, 128, 75.
[34] Wang, Y.; Wu, C.; Zhang, Q. Bioorg. Chem. 2019, 84, 468.
[35] Williams, L. K.; Zhang, X.; Caner, S. Nat. Chem. Biol. 2015, 92, 387.
[36] Akkarachiyasit, S.; Yibchokanun, S.; Wacharasindhu, S. Molecules 2011, 16, 2075.
[37] Liu B, Ao W W, Yang Y. J. Nanjing For. Univ., Nat. Sci. Ed. 2010, 34, 89(in Chinese). (刘兵, 敖汪伟, 杨杨, 南京林业大学学报(自然科学版), 2010, 34, 89.)
[38] Bashary, R.; Khatik, G. L. Bioorg. Chem. 2018, 82, 156.
[39] O. Trott, A. J. Olson. J. Comput. Chem. 2010, 31, 455.

诺蒎酮基噻唑腙类化合物的合成及对α-淀粉酶的抑制活性

Synthesis and α-Amylase Inhibitory Potential and Molecular Docking Study of Nopinone-Based Thiazolylhydrazone Derivatives

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