Synthesis and Biological Activities of Novel 2,5-Disubstituted- 1,3,4-thiadiazole Derivatives

doi:10.6023/cjoc201405020

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 129-136.DOI: 10.6023/cjoc201405020 Previous Articles Next Articles

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新型2,5-二取代-1,3,4-噻二唑衍生物的合成与生物活性

李英俊^a, 于洋^a, 靳焜^b, 高立信^c, 罗潼川^a, 盛丽^c, 邵昕^a, 李佳^c

a 辽宁师范大学化学化工学院大连 116029;
b 大连理工大学精细化工国家重点实验室大连 116012;
c 中国科学院上海药物研究所国家新药筛选中心药物研究国家重点实验室上海 201203

收稿日期:2014-05-12 修回日期:2014-08-01 发布日期:2014-09-25
通讯作者: 李佳 E-mail:chemlab.lnnu@163.com
基金资助:
辽宁省自然科学基金(No. 20102126)资助项目.

Synthesis and Biological Activities of Novel 2,5-Disubstituted- 1,3,4-thiadiazole Derivatives

Li Yingjun^a, Yu Yang^a, Jin Kun^b, Gao Lixin^c, Luo Tongchuan^a, Sheng Li^c, Shao Xin^a, Li Jia^c

a College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
b State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012;
c National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203

Received:2014-05-12 Revised:2014-08-01 Published:2014-09-25
Supported by:
Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126).

1. Synthesis and Biological Activities of Novel 2,5-Disubstituted- 1,3,4-thiadiazole Derivatives.PDF(6263KB)

Abstract

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·.

Key words: 2,5-disubstituted-1,3,4-thiadiazole, benzisoselenazolone, synthesis, bioactivity

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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]. Chin. J. Org. Chem., 2015, 35(1): 129-136.

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[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.)

新型2,5-二取代-1,3,4-噻二唑衍生物的合成与生物活性

Synthesis and Biological Activities of Novel 2,5-Disubstituted- 1,3,4-thiadiazole Derivatives

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