Syntheses and in vitro Antitumor Activities of N-Acetyl Pyrazolines and Diphenyl Etheryl N-Acetyl Bis-pyrazolines

doi:10.6023/cjoc201503034

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (9): 1985-1990.DOI: 10.6023/cjoc201503034 Previous Articles Next Articles

Notes

N-乙酰基吡唑啉衍生物和二苯醚基N-乙酰基双吡唑啉衍生物的合成及体外抗肿瘤活性

张应鹏^a, 谭伟^a, 杨云裳^a, 孙世琪^b, 郭慧琛^b

a 兰州理工大学石油化工学院兰州 730050;
b 中国农业科学院兰州兽医研究所兰州 730050

收稿日期:2015-03-31 修回日期:2015-05-06 发布日期:2015-05-26
通讯作者: 张应鹏 E-mail:yingpengzhang@126.com
基金资助:
甘肃省自然科学基金(No. 2014GS03265)资助项目.

Syntheses and in vitro Antitumor Activities of N-Acetyl Pyrazolines and Diphenyl Etheryl N-Acetyl Bis-pyrazolines

Zhang Yingpeng^a, Tan Wei^a, Yang Yunshang^a, Sun Shiqi^b, Guo Huichen^b

a School of Petrochemical Engineering, Lanzhou University of Technology, Lanzhou 730050;
b Lanzhou Veterinary Research Institute, Chinese Academy of Agricultural Sciences, Lanzhou 730046

Received:2015-03-31 Revised:2015-05-06 Published:2015-05-26
Supported by:
Project supported by the Natural Science Foundation of Gansu Province (No. 2014GS03265).

1. Syntheses and in vitro Antitumor Activities of N-Acetyl Pyrazolines and Diphenyl Etheryl N-Acetyl Bis-pyrazolines.PDF(1491KB)

Abstract

Seven N-acetyl pyrazolines 2a~2g and seven N-acetyl bis-pyrazolines 4a~4g with diphenyl etheryl moiety were synthesized and characterized by ¹H NMR,¹³C NMR, elemental analysis and ESI-MS, and their in vitro antitumor activities on A549, H1299 and MCF-7 were evaluated by 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl-2H-tetrazolium) (MTS) assay. The results showed those compounds exhibited potent antiproliferative effects on cancer cells, among them compound 3,3'-(4,4'-diphenyl ether)-5,5'-bi[1-acetyl-5-(benzo[d][1,3]dioxo-5-yl)-2-pyrazoline] (4e) showed significantly inhibited the growth of all three kinds of cancer cells, the IC₅₀ values of A549, H1299 and MCF-7 were 16.91, 10.09, 10.97 μmol/L, respectively.

Key words: N-acetyl pyrazoline, N-acetyl bis-pyrazoline, diphenyl ether, antitumor

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Zhang Yingpeng, Tan Wei, Yang Yunshang, Sun Shiqi, Guo Huichen. Syntheses and in vitro Antitumor Activities of N-Acetyl Pyrazolines and Diphenyl Etheryl N-Acetyl Bis-pyrazolines[J]. Chin. J. Org. Chem., 2015, 35(9): 1985-1990.

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[1] Yin, J. G.; Li, Y. W.; Li, J. Z. Chin. J. Org. Chem. 2011, 31, 1213 (in Chinese). (殷军港, 李韵伟, 李家柱, 有机化学, 2011, 31, 1213.)
[2] Zhou, M.; Lu, J. R.; Xing, C. W. Chin. J. Org. Chem. 2010, 30, 1201 (in Chinese). (邹敏, 卢俊瑞, 辛春伟, 有机化学, 2010, 30, 1201.)
[3] Khan, S. A.; Asiri, A. M.; Kumar, S.; Sharma, K. Chem.-Eur. J. 2014, 5, 85.
[4] Wang, Z. N.; Hu, D. Y.; Song, B. A. Chin. J. Org. Chem. 2009, 29, 1412 (in Chinese). (王振宁, 胡德禹, 宋宝安, 有机化学, 2009, 29, 1412.)
[5] Raghav, N.; Garg, S. Bioorg. Chem. 2014, 57, 43.
[6] Shen, Y. M.; Lv, P. C.; Chen, W.; Liu, P. G.; Zhang, M. Z.; Zhu, H. L. Eur. J. Med. Chem. 2010, 45, 3184.
[7] Long, Y. X.; Zhang, K. S.; Qiu, D. W. Chem. J.Chin. Univ. 1996, 17, 1247 (in Chinese). (龙韫先, 张克胜, 邱德文, 高等学校化学学报, 1996, 17, 1247.)
[8] Ye, J. H.; Ye, W. F.; Zhang, W. C. Chin. J. Org. Chem. 2011, 31, 1917 (in Chinese). (叶家海, 叶文芳, 张文超, 有机化学, 2011, 31, 1917.)
[9] Morgan, M. T.; Sumalekshmy, S.; Sarwar, M.; Beck H.; Crooke, S.; Fahrni, C. J. J. Phys. Chem. B 2014, 118, 14196.
[10] Bernal, A.; Simón, O.; Williams, T.; Caballero, P. Pest. Manage. Sci. 2014, 70, 798.
[11] Liu, J. F.; Li, D. F.; Tang, X.; Cai, R.; Han, X.; Xie, Z. Y. Chin. J. Org. Chem. 2010, 30, 1039 (in Chinese). (刘计福, 李东风, 唐鑫, 蔡然, 韩啸, 谢志元, 有机化学, 2010, 30, 1039.)
[12] Jin, M.; Lu, R.; Bao, C. Y.; Xu, T. H.; Zhao, Y. Y. Opt. Mater. 2004, 26, 85.
[13] Ma, Y. M.; Fen, C. L. Chin. J. Org. Chem. 2008, 28, 1697 (in Chinese). (马养民, 冯成亮, 有机化学, 2008, 28, 1697.)
[14] Bunyapaiboonsri, T.; Yoiprommarat, S.; Intereya, K.; Kocharin, K. Chem. Pharm. Bull. 2007, 55, 304.
[15] Xu, W. F.; Drug Design, People’s Medical Publishing House, Beijing, 2007, p. 65 (in Chinese). (徐文方, 药物设计学, 人民卫生出版社, 北京, 2007, p. 65.)
[16] Nepali, K.; Singh, G.; Turan, A.; Agarwal, A.; Sapra, S.; Kumar, R.; Dhar, K. L. Bioorg. Med. Chem. 2011, 19, 1950.
[17] Cuei, J. G.; Huang, L. L.; Huang, Y. M. Chin. J. Org. Chem. 2009, 29, 971 (in Chinese). (崔建国, 黄立梁, 黄燕敏, 有机化学, 2009, 29, 971.)
[18] Chang, M. Y.; Chen, Y. C.; Chan, C. K. Tetrahedron 2014, 70, 2257.
[19] Rafiee, E.; Rahimi, F. Monatsh. Chem. 2013, 144, 361.
[20] Stroba, A.; Schaeffer F.; Hindie, V.; Lopez-Garcia, L.; Adrian, I.; Fröhner, W.; Engel, M. J. Med. Chem. 2009, 52, 4683.
[21] Abdel-Halim, M.; Diesel, B.; Kiemer, A. K.; Abadi, A. H.; Hartmann, R. W.; Engel, M. J. Med. Chem.; 2014, 57, 6513.
[22] Nagwanshi, R.; Bakhru, M.; Jain, S. Med. Chem. Res. 2012, 21, 1587.
[23] Rueping, M.; Bootwicha, T.; Baars, H.; Sugiono, E. Beilstein J. Org. Chem. 2011, 7, 1680.
[24] Wang, Y.; Franzén, R. Synlett 2012, 925.
[25] Bandgar, B. P.; Gawande, S. S.; Bodade, R. G. Bioorg. Med. Chem. 2010, 18, 1364.
[26] Chardonnens, L.; Hammer, W. Helv. Chim. Acta 1968, 51, 2044.
[27] Chuev, V. P.; Nikitchenko, V. M.; Pivnenko, N. S.; Lavrushin, V. F. Russ. J. Org. Chem. 1986, 22, 66.
[28] Dilthey, W.; Bach, E.; Grütering, H.; Hausdörfer, E.; J. Prakt. Chem. 1927, 117, 337.
[29] Dilthey, W.; Neuhaus, L.; Reis, E.; Schommer, W. J. Prakt. Chem. 1929, 124, 81.
[30] Maccarone, E.; Cuffari, G.; Passerini, A. J. Chem. Res., Synop. 1991, 9, 240.
[31] Lv, P. C.; Sun, J.; Luo, Y.; Yang, Y.; Zhu, H. L. Bioorg. Med. Chem. Lett. 2010, 20, 4657.
[32] Congiu, C.; Onnis, V.; Vesci, L.; Castorina, M.; Pisano, C. Bioorg. Med. Chem. Lett. 2010, 18, 6238.
[33] Manna, F.; Chimenti, F.; Fioravanti, R.; Bolasco, A.; Secci, D.; Chimenti, P.; Scambia, G. Bioorg. Med. Chem. Lett. 2005, 15, 4632.

N-乙酰基吡唑啉衍生物和二苯醚基N-乙酰基双吡唑啉衍生物的合成及体外抗肿瘤活性

Syntheses and in vitro Antitumor Activities of N-Acetyl Pyrazolines and Diphenyl Etheryl N-Acetyl Bis-pyrazolines

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