Synthesis and Antitumor Activities of Alkyl 4-(Bis(4-fluorophenyl)-methyl)piperazine-1-carbodithioate Derivatives

doi:10.6023/cjoc201604037

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (12): 2981-2985.DOI: 10.6023/cjoc201604037 Previous Articles Next Articles

NOTE

4-[二(4-氟苯基)甲基]哌嗪-1-二硫代甲酸酯衍生物的合成及抗肿瘤活性研究

邓杰, 李爱暖, 李清寒, 丁勇, 杨学军, 陈峰

西南民族大学化学与环境保护工程学院成都 610041

收稿日期:2016-04-18 修回日期:2016-07-19 发布日期:2016-08-22
通讯作者: 李清寒 E-mail:lqhchem@163.com
基金资助:
四川省科技厅科技支撑计划（No. 2015NZ0033）和西南民族大学大学生创新创业训练基金（No. S201510656121）资助项目.

Synthesis and Antitumor Activities of Alkyl 4-(Bis(4-fluorophenyl)-methyl)piperazine-1-carbodithioate Derivatives

Deng Jie, Li Ainuan, Li Qinghan, Ding Yong, Yang XueJun, Chen Feng

College of Chemistry and Environmental Protection Engineering, Southwest University for Nationalities, Chengdu 610041

Received:2016-04-18 Revised:2016-07-19 Published:2016-08-22
Supported by:
Project supported by the Sichuan Provincial Department of Science and Technology (No. 2015NZ0033) and the Southwest University for Nationalities Students Innovation and Entrepreneurship Training (No. S201510656121).

1. Synthesis and Antitumor Activities of Alkyl 4-(Bis(4-fluorophenyl)-methyl)piperazine-1-carbodithioate Derivatives.PDF(1311KB)

Abstract

Thirteen new alkyl 4-(bis(4-fluorophenyl)methyl)piperazine-1-carbodithioatee derivatives were synthesized with 1-(bis(4-fluorophenyl)methyl)piperazine, substituted benzyl or alkyl bromide and methane-dithione as starting material in the presence of K₃PO₄. Their structures were determined by IR, MS and ¹H NMR. Preliminary bioassay indicated that twelve compounds exhibited good activities against CDC25B (the inhibition rates up to 99% at the concentration of 20 μg/mL), three compounds exhibited a certain degree against Leukemia HL-60 cell (the inhibition rates up to 54.59% at the concentration of 40 μmol/L).

Key words: 1-(bis(4-fluorophenyl)methyl)piperazine, carbodithioate, organic synthesis, antitumor activity

Cite this article

Deng Jie, Li Ainuan, Li Qinghan, Ding Yong, Yang XueJun, Chen Feng. Synthesis and Antitumor Activities of Alkyl 4-(Bis(4-fluorophenyl)-methyl)piperazine-1-carbodithioate Derivatives[J]. Chin. J. Org. Chem., 2016, 36(12): 2981-2985.

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[1] Goel, A.; Mazur, S. J.; Fattah, R. J.; Hartman, T. L.; Turpin, J. A.; Huang, M.-J.; Rice, W. G.; Appella, E.; Inman, J. K. Bioorg. Med. Chem. Lett. 2002, 12, 767.
[2] Soledade, M.; Pedras, C.; Sarma-Mamillapalle, V. K. J. Agric. Food Chem. 2012, 60, 7792.
[3] Carta, F.; Aggarwal, M.; Maresca, A.; Scozzafava, A.; McKenna, R.; Masini, E.; Supuran, C. T. J. Med. Chem. 2012, 55, 172.
[4] Suh, Y.-G.; Lee, Y.-S.; Min, K.-H.; Park, O.-H.; Kim, J.-K.; Seung, H.-S.; Seo, S.-Y.; Lee, B.-Y.; Nam, Y.-H.; Lee, K.-O.; Kim, H.-D.; Park, H.-G.; Lee, J.-W.; Oh, U.; Lim, J.-O.; Kang, S.-U.; Kil, M.-J.; Koo, J.-Y.; Shin, S.-S.; Joo, Y.-H.; Kim, J.-K.; Jeong, Y.-S.; Kim, S.-Y.; Park, Y.-H. J. Med. Chem. 2005, 48, 5823.
[5] Li, Q.-H.; Ding, Y.; Huang, N.-W. Chin. Chem. Lett. 2014, 25, 1296.
[6] Ding, Y.; Zhang, Z.; Zhang, G.; Mo, S.; Li, Q.-H.; Zhao, Z.-G. Res. Chem. Intermed. 2016, 42, 3105.
[7] Greene, T. W.; Wuts, P. G. M. Protecting Groups in Organic Synthesis, 3rd ed., Wiley Interscience, New York, 1999, pp. 484~485.
[8] Bhadra, S.; Saha, A.; Ranu, B. C. Green Chem. 2008, 10, 1224.
[9] Morf, P.; Raimondi, F.; Nothofer, H. G.; Schnyder, B.; Yasuda, A.; Wessels, J. M.; Thomas A.; Jung, T. A. Langmuir 2006, 22, 658.
[10] Nieuwenhuizen, P. J.; Ehlers, A. W.; Haasnoot, J. G.; Janse, S. R.; Reedi, J.; Baerends, E. J. J. Am. Chem. Soc. 1999, 121, 163.
[11] Wood, M. R.; Duncalf, D. J.; Rannard, S. P.; Perrier, S. Org. Lett. 2006, 8, 553.
[12] Tan, J.; Liang, F.-H.; Wang, Y.-M.; Cheng, X.; Liu, Q.; Yuan, H.-J. Org. Lett. 2008, 10, 2485.
[13] Carta, F.; Aggarwal, M.; Maresca, A.; Scozzafava, A.; McKenna, R.; Masini, E.; Supuran, C. T. J. Med. Chem. 2012, 55, 1721.
[14] Guo, S.-R.; Yuan, Y.-Q.; Zhang, C.-N. Chin. J. Org. Chem. 2012, 32, 907(in Chinese).(郭圣荣, 袁艳琴, 张春牛, 有机化学, 2012, 32, 907.)
[15] Kuznetsova, L.; Ungureanu, M. I.; Pepe, A. J. Fluorine Chem. 2004, 125, 415.
[16] Sun, X. H.; Li, S. J.; Liu, Y. F.; Chen, B.; Jia, Y. Q.; Tao, Y. Chin. J. Org. Chem. 2007, 27, 82(in Chinese).(孙晓红, 李淑娟, 刘源发, 陈邦, 贾婴琦, 陶燕, 有机化学, 2007, 27, 82.)
[17] Haga, T.; Fujikawa, K.; Koyanag, T.; Nakajima, T.; Hayashi, K. Heterocycles 1984, 22, 117.
[18] Yoshida, S.; Meyer, O. G. J.; Rosen, T. C.; Haufe, G.; Song, Y.; Sloan, M. J.; Kirk, K. L. J. Med. Chem. 2004, 47, 1796.
[19] Shelke, S. N.; Mhaske, G. R.; Bonifàcio, V. D. B.; Gawande, M. B. Bioorg. Med. Chem. Lett. 2012, 22, 5727.
[20] Adsule, S.; Barve, V.; Chen, D.; Ahmed, F.; Dou, Q. P.; Padhye, S.; Sarkar, F. H. J. Med. Chem. 2006, 49, 7242.
[21] Ge, Z.-M.; Guo, B.-G.; Wang, H.-Y.; Cheng, T.-M.; Li, R.-T. J. Peking Univ. (Health Sci.) 2001, 33, 213(in Chinese).(葛泽梅, 郭保国, 王红宇, 程铁明, 李润涛, 北京大学学报(医学版), 2001, 33, 213.)
[22] Li, Q.-H.; Ding, Y.; Zhang G.; Zhang, Z.; Mong, S. Chin. J. Org. Chem. 2016, 36, 83(in Chinese).(李清寒, 张刚, 张震, 莫松, 有机化学, 2016, 36, 83.)

4-[二(4-氟苯基)甲基]哌嗪-1-二硫代甲酸酯衍生物的合成及抗肿瘤活性研究

Synthesis and Antitumor Activities of Alkyl 4-(Bis(4-fluorophenyl)-methyl)piperazine-1-carbodithioate Derivatives

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