Chinese Journal of Organic Chemistry >
Synthesis and Biological Activities of Novel 2,5-Disubstituted- 1,3,4-thiadiazole Derivatives
Received date: 2014-05-12
Revised date: 2014-08-01
Online published: 2014-09-25
Supported by
Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126).
Sixteen novel 2,5-disubstituted-1,3,4-thiadiazole derivatives containing benzisoselenazolone moiety 7a～7p were synthesized by the reaction of 2-amino-5-substituted-1,3,4-thiadiazoles (2) with ortho-(chloroseleno)benzoyl chloride (6). The structures were characterized by IR, 1H NMR spectra and elemental analysis. Their biological activities were evaluated. The experimental results indicate that some compounds exhibit inhibitory activity against cell division cycle 25B phosphatase (Cdc25B) (IC50=1.67～6.66 mmol·L-1). All the target compounds showed good inhibitory activity against protein tyrosine phosphatase 1B (PTP1B) (IC50=0.73～4.50 mmol·L-1), and some compounds exhibited higher inhibitory activity than positive control oleanolic acid (IC50=1.90 mmol·L-1). Compound 7k displayed antitumor activity in vitro for human colon cancer (HCT-8) cell (IC50=12.54 mmol·L-1). Some compounds showed the medium scavenging ability for hydroxyl radical (HO·) and superoxide anion (O2·-), but no scavenging ability for DPPH·.
Li Yingjun , Yu Yang , Jin Kun , Gao Lixin , Luo Tongchuan , Sheng Li , Shao Xin , Li Jia . Synthesis and Biological Activities of Novel 2,5-Disubstituted- 1,3,4-thiadiazole Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(1) : 129 -136 . DOI: 10.6023/cjoc201405020
[1] Kumar, D.; Kumar, N. M.; Noel, B.; Kavita, S. Eur. J. Med. Chem. 2012, 55, 432.
[2] Yang, X.-H.; Xiang, L.; Li, X.; Zhao, T.-T.; Zhang, H.; Zhou, W.-P.; Wang, X.-M.; Gong, H.-B.; Zhu, H.-L. Bioorg. Med. Chem. 2012, 20, 2789.
[3] Mougenot, P.; Namane, C.; Fett, E.; Camy, F.; Dadji-Faïhun, R.; Langot, G.; Monseau, C.; Onofri, B.; Pacquet, F.; Pascal, C.; Crespin, O.; Ben-Hassine, M.; Ragot, J.-L.; Van-Pham, T.; Philippo, C.; Chatelsin-Egger, F.; Péron, P.; Bail, J. C. L.; Guillot, E.; Chsmiot-Clerc, P.; Chabanaud, M. A.; Pruniaux, M. P.; Schmidt, F.; Venier, O.; Nicolaï, E.; Viviani, F. Bioorg. Med. Chem. Lett. 2012, 22, 2497.
[4] Sheppeck II, J. E.; Gilmore, J. L.; Xiao, H. Y.; Dhar, T. G. M.; Nirsch, D.; Doweyko, A. M.; Sack, J. S.; Corbett, M. J.; Malley, M. F.; Gougoutas, J. Z.; Mckay, L.; Cunningham, M. D.; Habte, S. F.; Dodd, J. H.; Nadler, S. G.; Somerville, J. E.; Barrish, J. C. Bioorg. Med. Chem. Lett. 2013, 23, 5442.
[5] Rebolledo, C. L.; Sotelo-Hitschfeld, P.; Brauchi, S.; Olavarría, M. Z. Eur. J. Med. Chem. 2013, 66, 193.
[6] Suzuki, K.; Hamada, Y.; Nguyen, J. T.; Kiso, Y. Bioorg. Med. Chem. 2013, 21, 6665.
[7] Luo, Z.-H.; Chen, B.-Q.; He, S.-Y.; Shi, Y.-P.; Liu, Y.-M.; Li, C.-W. Bioorg. Med. Chem. Lett. 2012, 22, 3191.
[8] Chen, B.-Q.; Shi, Y.-P.; Li, C.-W.; Liu, Y.-M. Chemistry 2011, 74, 709 (in Chinese). (陈宝泉, 史艳萍, 李彩文, 刘玉刚, 化学通报, 2011, 21, 709.)
[9] Pietka-Ottlik, M.; Potaczek, P.; Piasecki, E.; Mlochowski, J. Molecules 2010, 15, 8214.
[10] Xiao, Y.-X.; Liu, X.-F.; Xu, H.-S. Chin. J. Pharm. 1997, 28, 535 (in Chinese). (肖颖歆, 刘秀芳, 徐汉生, 中国医药工业杂志, 1997, 28, 535.)
[11] Messali, M.; Christiaens, L. E.; Alshahateet, S. F.; Kooli F. Tetrahedron Lett. 2007, 48, 7448.
[12] Bijian, K.; Zhang, Z. W.; Xu, B.; Jie, S.; Chen, B.; Wan, S. B.; Wu, J. H.; Jiang, T.; Alaoui-Jamali, M. A. Eur. J. Med. Chem. 2012, 48, 143.
[13] Matsushita, T.; Fukuda, K.; Yamamoto, H.; Yamazaki, K.; Tomiyama, T.; Oh, M.; Hamanishi, C. Mod. Rheumatol. 2004, 14, 25.
[14] Wójtowicz, H.; Kloc, K.; Maliszewska, I.; M?ochowski, J.; Pi?tka, M.; Piasecki, E. Farmaco 2004, 59, 863.
[15] Mao, F.; Chen, J.-W.; Zhou, Q.; Luo, Z.-H.; Huang, L.; Li, X.-S. Bioorg. Med. Chem. Lett. 2013, 23, 6737.
[16] Luo, Z.-H.; Liang, L.; Sheng, J.-F.; Pang, Y.-Q.; Li, J.-H.; Huang, L.; Li, X.-S. Bioorg. Med. Chem. 2014, 22, 1355.
[17] Gijsen, H. J. M.; De Cleyn, M. A. J.; Surkyn, M.; Van Lommen, G. R. E.; Verbist, B. M. P.; Nijsen, M. J. M. A.; Meert, T.; Wauwe, J. V.; Aerssens, J. Bioorg. Med. Chem. Lett. 2012, 22, 547.
[18] Li, Y.-J.; Shao, X.; Gao, L.-X.; Jin, K.; Sheng, L.; Luo, T.-C.; Yu, Y.; Li, J. Chin. J. Org. Chem. 2013, 33, 2178 (in Chinese). (李英俊, 邵昕, 高立信, 靳焜, 盛丽, 罗潼川, 于洋, 李佳, 有机化学, 2013, 33, 2178.)
[19] Li, Y.-J.; Luo, T.-C.; Jin, K.; Gao, L.-X.; Shao, X.; Sheng, L.; Yu, Y.; Li, J. Chin. J. Org. Chem. 2014, 34, 325 (in Chinese). (李英俊, 罗潼川, 靳焜, 高立信, 邵昕, 盛丽, 于洋, 李佳, 有机化学, 2014, 34, 325.)
[20] Li, J.; Guo, S.-J.; Su, H.; Han, L.-J.; Shi, D.-Y. Chin. Chem. Lett. 2008, 19, 1290.
[21] Sibille, E.; Bana, E.; Chaouni, W.; Diederich, M.; Bagrel, D.; Chaimbault, P. Anal. Biochem. 2012, 430, 83.
[22] Huang, W.-G.; Li, J.-Y.; Luo, Y.; Li, J.; Lu, W. Chin. Chem. Lett. 2009, 20, 1461.
[23] Guo, Z.-R. Acta Pharmacol. Sin. 2008, 43, 227 (in Chinese). (郭宗儒, 药学学报, 2008, 43, 227.)
[24] Ahsan, M. J.; Samy, J. G.; Khalilullah, H.; Nomani, M. S.; Saraswat, P.; Gaur, R.; Singh, A. Bioorg. Med. Chem. Lett. 2011, 21, 7216.
[25] Suetsuna, K.; Ukeda, H.; Ochi, H. J. Nutr. Biochem. 2000, 11, 128.
[26] Jackson, H. L.; Cardounel, A. J.; Zweier, J. L.; Lockwood, S. F. Bioorg. Med. Chem. Lett. 2004, 14, 3985.
[27] Mishra, K.; Ojha, H.; Chaudhury, N. K. Food Chem. 2012, 130, 1036.
[28] Lamani, R. S.; Shetty, N. S.; Kamble, R. R.; Khazi, I. A. M. Eur. J. Med. Chem. 2009, 44, 2828.
[29] An, J. M.S. Thesis, Liaoning Normal University, Dalian, 2012 (in Chinese). (安静, 硕士论文, 辽宁师范大学, 大连, 2012.)
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