Chinese Journal of Organic Chemistry >
Synthesis and Antitumor Activities of Alkyl 4-(Bis(4-fluorophenyl)-methyl)piperazine-1-carbodithioate Derivatives
Received date: 2016-04-18
Revised date: 2016-07-19
Online 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).
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).
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]. Chinese Journal of Organic Chemistry, 2016 , 36(12) : 2981 -2985 . DOI: 10.6023/cjoc201604037
[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.)
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