Synthesis and Antitumor Activity of N-[4-(t-Butyl)-5-benzylthiazol-2-yl]amininoacetamides

doi:10.6023/cjoc201610018

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 675-682.DOI: 10.6023/cjoc201610018 Previous Articles Next Articles

ARTICLE

N-(4-叔丁基-5-苄基噻唑-2-基)氨基乙酰胺的合成与抗肿瘤活性

唐玉婷, 丁娜, 伍智林, 叶姣, 申坤, 胡艾希

湖南大学化学化工学院长沙 410082

收稿日期:2016-10-12 修回日期:2016-11-16 发布日期:2016-11-29
通讯作者: 胡艾希,E-mail:axhu@hnu.edu.cn E-mail:axhu@hnu.edu.cn
基金资助:
国家自然科学基金（No.21442014）资助项目.

Synthesis and Antitumor Activity of N-[4-(t-Butyl)-5-benzylthiazol-2-yl]amininoacetamides

Tang Yuting, Ding Na, Wu Zhilin, Ye Jiao, Shen Kun, Hu Aixi

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received:2016-10-12 Revised:2016-11-16 Published:2016-11-29
Contact: 10.6023/cjoc201610018 E-mail:axhu@hnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21442014).

1. Synthesis and Antitumor Activity of N-[4-(t-Butyl)-5-benzylthiazol-2-yl]amininoacetamides.PDF(1849KB)

Abstract

The antitumor activity research of N-(thiazol-2-yl) amide derivatives has been the focus of scholars. Physiologi-cally active substances containing amines widely exist in nature. A series of novel N-(4-(t-butyl)-5-benzylthiazol-2-yl) aminoacetamides were synthesized, and their structures were confirmed by ¹H NMR, ¹³C NMR and elemental analysis. These compounds were evaluated for their in vitro anticancer activity on A549, Hela and MCF-7 cells. Most of the investigated compounds exhibited broad-spectrum antitumor activity. Compound 1t displayed significant activity against Hela cancer cells with IC₅₀ value of (6.4±2.2) μmol/L. The AO/EB staining and cell cycle experiments were carried out on the preferred com-pound 1t. The result showed that compound 1t could significantly induce apoptosis of tumor cells and arrest the Hela cells in the S phase.

Key words: thiazoleacetamide, morpholine, synthesis, antitumor activity

Cite this article

Tang Yuting, Ding Na, Wu Zhilin, Ye Jiao, Shen Kun, Hu Aixi. Synthesis and Antitumor Activity of N-[4-(t-Butyl)-5-benzylthiazol-2-yl]amininoacetamides[J]. Chin. J. Org. Chem., 2017, 37(3): 675-682.

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[1] Pokhodylo, N.; Shyyka, O.; Matiychuk, V. Med. Chem. Res. 2014, 23, 2426.
[2] Lee, Y. S. E.; Chuang, S. H.; Huang, L. Y. L.; Lai, C. L.; Lin, Y. H.; Yang, J. Y.; Liu, C. W.; Yang, S. C.; Lin, H. S.; Chang, C. C.; Lai, J. Y.; Jian, P. S.; Lam, K.; Chang, J. M.; Lau, J. Y. N.; Huang, J. J. J. Med. Chem. 2014, 57, 4098.
[3] Gorczynski, M. J.; Leal, R. M.; Mooberry, S. L.; Bushweller, J. H.; Brown, M. L. Bioorg. Med. Chem. 2004, 12, 1029.
[4] Jiang, F. C.; Cheng, C. Y. Acta Pharm. Sin. 2006, 41, 727 (in Chinese).(姜凤超, 成冲云, 药学学报, 2006, 41, 727.)
[5] Bjoern, E.; Guido, K.; Christian, H. CN 101277692, 2007[Chem. Abstr. 2007, 146, 163101].
[6] Chen, Y.; Wang, H.; Dinesh, A.; Zhou, C. H. Chin. J. Org. Chem. 2016, 36, 1 (in Chinese).(程宇, 王辉, Dinesh Addla, 周成合, 有机化学, 2016, 36, 1.)
[7] Liao, Q. H.; Lin, S.; Deng, R. H.; Huang, Z. Q.; Deng, K. Y.; Yan, Z. H. Chin. J. Org. Chem. 2015, 35, 1923 (in Chinese).(廖启华, 林森, 邓瑞红, 黄志强, 邓柯玉, 严兆华, 有机化学, 2015, 35, 1923.)
[8] (a) Hu, A. X.; Huo, S. F.; Xia, S.; Li, W.; Ye, J.; Peng, J. M.; Xiang, J. N. CN 102070556, 2011[Chem. Abstr. 2011, 154, 615156].
(b) Hu, A. X.; Li, W.; Xia, S.; Ye, J.; Huo, S. F.; Zou, S. S.; Peng, J. M.; Xiang, J. N. CN 102319244, 2012[Chem. Abstr. 2012, 156, 194844].
[9] Makam, P.; Kannan, T. Eur. J. Med. Chem. 2014, 87, 643.
[10] Turan-Zitouni, G.; Özdemir, A.; Kaplanc?kli, Z. A. Phosphorus, Sulfur, Silicon Relat. Elem. 2011, 186, 233.
[11] Kouatly, O.; Geronikaki, A.; Kamoutsis, C.; Hadjipavlou-Litina, D.; Eleftheriou, P. Eur. J. Med. Chem. 2009, 44, 1198.
[12] Siddiqui, N.; Ahsan, W. Eur. J. Med. Chem. 2010, 45, 1536.
[13] Iino, T.; Tsukahara, D.; Kamata, K.; Sasaki, K.; Ohyama, S.; Hosaka, H.; Hasegawa, T.; Chiba, M.; Nagata, Y.; Eiki, J.; Nishimura, T. Bioorg. Med. Chem. 2009, 17, 2733.
[14] Abdel-Wahab, B. F.; Mohamed, S. F.; Amr, A. E. G. E.; Abdalla, M. Monatsh. Chem. 2008, 139, 1083.
[15] Rostom, S. A. F.; Faidallah, H. M.; Radwan, M. F.; Badr, M. H. Eur. J. Med. Chem. 2014, 76, 170.
[16] Gurdal, E. E.; Durmaz, I.; Cetin-Atalay, R.; Yarim, M. J. Enzyme Inhib. Med. Chem. 2015, 30, 649.
[17] Cui, J. G.; Zhao, D. D.; He, D. M.; Huang, Y. M.; Liu, Z. P.; Lin, Q. F.; Shi, H. X.; Gan, C. F. Chin. J. Org. Chem. 2016, 36, 630 (in Chinese).(崔建国, 赵丹丹, 何冬梅, 黄燕敏, 刘志平, 林啟福, 石海信, 甘春芳, 有机化学, 2016, 36, 630.)
[18] (a) Hu, A. X.; Peng, J. M.; Fang, Y. L.; Shen, K.; Li, W.; Yan, X. W. CN 103333132, 2013[Chem. Abstr. 2013, 158, 359731].
(b) Hu, A. X.; Peng, J. M.; Shen, K.; Li, W.; Yan, X. W.; Fang, Y. L. CN 103601697, 2013[Chem. Abstr. 2013, 158, 446959].
[19] Peng, J. M. Ph.D. Dissertation, Hunan University, Changsha, 2013, (in Chinese).(彭俊梅, 博士论文, 湖南大学, 长沙, 2013.)
[20] Wu, Z. L.; Fang, Y. L.; Tang, Y. T.; Xiao, M. W.; Ye, J.; Li, G. X. A.; Hu, X. Med. Chem. Commun. 2016, 7, 1768.
[21] Peng, J. M.; Li, W.; Shen, K.; Huo, S. F.; Ye, J.; Hu, A. X. Chem. J. Chin. Univ. 2013, 34, 1646 (in Chinese).(彭俊梅, 李婉, 申坤, 霍素芳, 叶姣, 胡艾希, 高等学校化学学报, 2013, 34, 1646.)

N-(4-叔丁基-5-苄基噻唑-2-基)氨基乙酰胺的合成与抗肿瘤活性

Synthesis and Antitumor Activity of N-[4-(t-Butyl)-5-benzylthiazol-2-yl]amininoacetamides

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