Citation: Zhang Chenglu, Sun Xiaona, Pu Yuxin, Li Chuanyin, Sun Lijie, Wang Jing, Li Yizheng. Design, Synthesis and Activities of Multiheterocyclic Modified Novel Molecules Using 1, 3-Selenazole as Template[J]. Chinese Journal of Organic Chemistry, ;2017, 37(2): 440-454. doi: 10.6023/cjoc201607024 shu

Design, Synthesis and Activities of Multiheterocyclic Modified Novel Molecules Using 1, 3-Selenazole as Template

  • Corresponding author: Zhang Chenglu, zhangchenglu@lnnu.edu.cn
  • Received Date: 15 July 2016
    Revised Date: 3 September 2016

    Fund Project: the Science and Technology Research Program of Liaoning Provincial Department of Education 2009A426

Figures(8)

  • Six kinds, twenty-two novel target molecules were first designed and synthesized by using substituted 1, 3-selenazole as a template, which were modified by 1, 2, 4-triazole, tetrazole, oxadiazole, pyrazole, 1, 2, 4-triazine and succinic imide respectively. Their structures were confirmed by IR, NMR and HRMS. The inhibitory activities of the target molecules against cell division cycle 25B phosphatase (Cdc25B) were evaluated. As a result, thirteen compounds exhibited good inhibitory activities. The IC50 values of five compounds were lower than the positive reference Na3VO4 and were expected to be anticancer drugs leading compounds. The analysis of structure-activity relationship found that the introduction of multinitrgon-heterocyclic triazole, tetrazole and triazine, thiadiazole and oxadiazole containing amino or mercapto group onto 1, 3-selenazole were expected to obtain novel excellent bioactivity organic selenium containing molecules.
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    1. [1]

      Karegoudar, P.; Karthikeyan, M. S.; Prasad, D. J.; Mahalinga, M.; Holla, B. S.; Kumari, N. S. Eur. J. Med. Chem. 2008, 43(2), 261.  doi: 10.1016/j.ejmech.2007.03.014

    2. [2]

      Bharti, S. K.; Nath, G.; Tilak, R.; Singh, S. K. Eur. J. Med. Chem. 2010, 45(2), 651.  doi: 10.1016/j.ejmech.2009.11.008

    3. [3]

      Mohammad, H.; Mayhoub, A. S.; Cushman, M.; Seleem, M. N. J. Antibiot. 2015, 68, 259.  doi: 10.1038/ja.2014.142

    4. [4]

      de Sa, N. P.; Lino, C. I.; Fonseca, N. C.; Borelli, B. M.; Ramos, J. P.; Souza-Fagundes, E. M.; Rosa, C. A.; Santos, D. A.; Oliveira, R. B.; Johann, S. Eur. J. Med. Chem. 2015, 102, 233.  doi: 10.1016/j.ejmech.2015.07.032

    5. [5]

      Chimenti, F.; Bizzarri, B.; Maccioni, E.; Secci, D.; Bolasco, A.; Fioravanti, R.; Chimenti, P.; Granese, A.; Carradori, S.; Rivanera, D.; Lilli, D.; Zicari, A.; Distinto, S. Bioorg. Med. Chem. Lett. 2007, 17(16), 4635.  doi: 10.1016/j.bmcl.2007.05.078

    6. [6]

      Youssef, A. M.; Malki, A.; Badr, M. H. Med. Chem. 2012, 8, 151.  doi: 10.2174/157340612800493719

    7. [7]

    8. [8]

      Taori, K.; Paul, V. J.; Luesch, H. J. Am. Chem. Soc. 2008, 130(6), 1806.  doi: 10.1021/ja7110064

    9. [9]

      Stadtman, T. C. Ann. N. Y. Acad. Sci. 2000, 899, 399.

    10. [10]

      Metanis, N.; Keinan, E.; Dawson, P. E. J. Am. Chem. Soc. 2006, 128, 16684.  doi: 10.1021/ja0661414

    11. [11]

      Nishina, A.; Kimura, H.; Kozawa, K.; Sommen, G.; Nakamura, T.; Heimgartner, H.; Koketsu, M.; Furukawa, S. Toxicol. Appl. Pharmacol. 2011, 257(3), 388.  doi: 10.1016/j.taap.2011.09.022

    12. [12]

      Venardos, K. M.; Perkins, A.; Headrick, J. Curr. Med. Chem. 2007, 14(14), 1539.  doi: 10.2174/092986707780831078

    13. [13]

      Sanmartin, C.; Plano, D.; Font, M. Curr. Med. Chem. 2011, 18(30), 4635.  doi: 10.2174/092986711797379249

    14. [14]

      Ninomiya, M.; Garud, D. R.; Koketsu, M. Coord. Chem. Rev. 2011, 255(23), 2968.

    15. [15]

      Farag, A. M.; Mayhoub, A. S.; Barakat, S. E.; Bayomi, A. H. Bioorg. Med. Chem. 2008, 16(2), 881.  doi: 10.1016/j.bmc.2007.10.015

    16. [16]

      Xia, Y.; Fan, C. D.; Zhao, B. X.; Zhao, J.; Shin, D. S.; Miao, J. Y. Eur. J. Med. Chem. 2008, 43(11), 2347.  doi: 10.1016/j.ejmech.2008.01.021

    17. [17]

      Xia, Y., Dong, Z. W.; Zhao, B. X.; Ge, X.; Meng, N.; Shin, D. S.; Miao, J. Y. Bioorg. Med. Chem. 2007, 15(22), 6893.  doi: 10.1016/j.bmc.2007.08.021

    18. [18]

      Simlot, R.; Izydore, R. A.; Wong, O. T. J. Pharm. Sci. 1994, 83, 367.  doi: 10.1002/jps.2600830320

    19. [19]

      Kanagarajan, V.; Thanusu, J.; Ezhilarasi, M. R. Chem. Hetero-cycl. Compd. 2011, 47, 60.  doi: 10.1007/s10593-011-0720-5

    20. [20]

      Mallakpour, S.; Rafiee, Z. Polym. Adv. Technol. 2008, 19(8), 1015.  doi: 10.1002/pat.v19:8

    21. [21]

      Mallakpour, S.; Rafiee, Z. Polym. Bull. 2008, 60(4), 507.  doi: 10.1007/s00289-008-0888-8

    22. [22]

      Mallakpour, S.; Rafiee, Z. Polymer 2007, 48(19), 5530.  doi: 10.1016/j.polymer.2007.07.036

    23. [23]

      Mallakpour, S.; Rafiee, Z. Synlett 2007 (8), 1255.

    24. [24]

      Abu-Zaied, M. A. Z.; Nawwar, G. A. M.; Swellem, R. H.; El-Sayed, S. H. Pharmacol. Pharm. 2012, 3, 254.  doi: 10.4236/pp.2012.32034

    25. [25]

      Sahu, V. K. R.; Singh, A. K.; Yadav, D. Int. J. ChemTech. Res. 2011, 3, 1362.

    26. [26]

      Jain, S. K.; Yadav, A. K.; Nayak, P. Int. J. Pharm. Sci. Drug Res. 2011, 3, 230.

    27. [27]

      Ouyang, X.; Piatnitski, E. L.; Pattaropong, V.; Chen, X. L.; He, H. Y.; Kiselyov, A. S.; Velankar, A.; Kawakami, J.; Labelle, M.; Smith, L.; Lohman, J.; Lee, S. P.; Malikzay, A.; Fleming, J.; Gerlak, J.; Wang, Y.; Rosler, R. L.; Zhou, K.; Mitelman, S.; Camara, M.; Surguladze, D.; Doody, J. F.; Tuma, M. C. Bioorg. Med. Chem. Lett. 2006, 16(22), 1191.

    28. [28]

      Lewis, J. R. Nat. Prod. Rep. 1999, 16, 389.  doi: 10.1039/a802500b

    29. [29]

      Dorville, A.; McCort-Tranchepain, I.; Vichard, D.; Sather, W.; Maroun, R.; Ascher, P.; Roques, B. P. J. Med. Chem. 1992, 35(14), 2551.  doi: 10.1021/jm00092a005

    30. [30]

      Jaen, J. C.; Wise, L. D.; Caprathe, B. W.; Tecle, H.; Bergmeier, S.; Humblet, C. C.; Heffner, T. G.; Meltzer, L. T.; Pugsley, T. A. J. Med. Chem. 1990, 33(1), 311.  doi: 10.1021/jm00163a051

    31. [31]

      Clemence, F.; Martet, O. L.; Delevallee, F.; Benzoni, J.; Jonanen, A.; Jouquey, S.; Mouren, M.; Deraedt, R. J. Med. Chem. 1988, 31(7), 1453.  doi: 10.1021/jm00402a034

    32. [32]

      Hargrave, K. D.; Hess, F. K.; Oliver, J. T. J. Med. Chem. 1983, 26(8), 1158.  doi: 10.1021/jm00362a014

    33. [33]

      Tsuji, K.; Ishikawa, H. Bioorg. Med. Chem. Lett. 1994, 4(13), 1601.  doi: 10.1016/S0960-894X(01)80574-6

    34. [34]

      Bell, F. W.; Cantrell, A. S.; Hoberg, M.; Jaskunas, S. R.; Johansson, N. J.; Jordan, C. L.; Kinnick, M. D.; Lind, P.; MorinJr, J. M. J. Med. Chem. 1995, 38(25), 4929.  doi: 10.1021/jm00025a010

    35. [35]

      My Hang, V. H.; Michael, D. C.; Thomas, J. M.; Modi, W. Proc. Natl. Acad. Sci. 2006, 103(27), 10322.  doi: 10.1073/pnas.0604241103

    36. [36]

      My Hang, V. H. WO 2008054538, 2008 [Chem. Abstr. 2008, 148, 474992].

    37. [37]

      Gao, H. X.; Shreeve, J. M. Chem. Rev. 201l, 111(11), 7377.  doi: 10.1021/cr200039c

    38. [38]

      Huang, M. Z.; Luo, F. X.; Mo, H. B.; Ren, Y. G.; Wang, X. G.; Ou, X. M.; Lei, M. X.; Liu, A. P.; Huang, L.; Xu, M. C. J. Agric. Food Chem. 2009, 57(20), 9585.  doi: 10.1021/jf901897f

    39. [39]

      Lawson, E. C.; Luci, D. K.; Ghosh, S.; Kinney, W. A.; Reynolds, C. H.; Qi, J.; Smith, C. E.; Wang, T. P.; Minor, L. K.; Haertlein, B. J.; Parry, T. J.; Damiano, B. P.; Maryanoff, B. E. J. Med. Chem. 2009, 52(23), 7432.  doi: 10.1021/jm900683d

    40. [40]

      Iwai, Y.; Takahashi, H.; Hatakeyama, D.; Motoshima, K.; Ishikawa, M.; Sugita, K.; Hashimoto, Y.; Harada, Y.; Itamura, S.; Odagiri, T.; Tashiro, M.; Sei, Y.; Yamaguchi, K.; Kuzuhara, T. Bioorg. Med. Chem. 2010, 18(14), 5379.  doi: 10.1016/j.bmc.2010.05.035

    41. [41]

      Kishida, K.; Aoyama, A.; Hashimoto, Y. Chem. Pharm. Bull. 2010, 58(11), 1525.  doi: 10.1248/cpb.58.1525

    42. [42]

      Kolukisaoglu, Ü.; Wendler, C.; Goerdes, D. J. Enzyme Inhib. Med. Chem. 2010, 25(6), 876.  doi: 10.3109/14756360903508448

    43. [43]

      Kaminski, K.; Obniska, J.; Wiklik, B.; Atamanyuk, D. Eur. J. Med. Chem. 2011, 46(8), 4634.

    44. [44]

      Bansode, T. N.; Shelke, J. V.; Dongre, V. G. Eur. J. Med. Chem. 2009, 44(12), 5094.  doi: 10.1016/j.ejmech.2009.07.006

    45. [45]

      Huang, W. G.; Jiang, Y. Y.; Li, Q.; Li, J.; Li, J. Y.; Lu, W.; Cai, J. C. Tetrahedron 2005, 61(7), 1863.  doi: 10.1016/j.tet.2004.12.033

    46. [46]

      Sun, L. P.; Shen, Q.; Piao, H. H.; Ma, W. P.; Gao, L. X.; Zhang, W.; Nan, F. J.; Li, J.; Piao, H. R. Eur. J. Med. Chem. 2011, 46(9), 3630.  doi: 10.1016/j.ejmech.2011.05.027

    47. [47]

      Shi, L.; Yu, H. P.; Zhou, Y. Y.; Du, J. Q.; Shen, Q.; Li, J. Y.; Li, J. Acta Pharmacol. Sin. 2008, 29, 278.  doi: 10.1111/aphs.2008.29.issue-2

    48. [48]

      Cao, S.; Foster, C.; Lazo, J. S.; Kingston, D. G. I. Bioorg. Med. Chem. 2005, 13(17), 5094.  doi: 10.1016/j.bmc.2005.04.070

    49. [49]

      Suzanne, F.; Stephen, J. E.; Anthony, F. H. J. Org. Chem. 2004, 69(14), 4663.  doi: 10.1021/jo049748g

    50. [50]

      Hua, G.; Li, Y.; Slawin, A. M. Z.; Woollines, J. D. Org. Lett. 2006, 8(23), 5251.  doi: 10.1021/ol062053c

    51. [51]

      Li, C.; Liu, J. C.; Li, Y. R.; Gou, C.; Zhang, M. L.; Liu, H. Y.; Li, X. Z.; Zheng, C. J.; Piao, H. R. Bioorg. Med. Chem. Lett. 2015, 25, 3052.  doi: 10.1016/j.bmcl.2015.04.081

    52. [52]

      Puthiyapurayil, P.; Poojarya, B.; Chikkanna, C.; Buridipad, S. K. Eur. J. Med. Chem. 2012, 53, 203.  doi: 10.1016/j.ejmech.2012.03.056

    53. [53]

      Banerjee, A. G.; Das, N.; Shengule, S. A.; Srivastava, R. S.; Shrivastava, S. K. Eur. J. Med. Chem. 2015, 101, 81.  doi: 10.1016/j.ejmech.2015.06.020

    54. [54]

      Bondock, S.; Fadaly, W.; Metwally, M. A. Eur. J. Med. Chem. 2010, 45, 3692.  doi: 10.1016/j.ejmech.2010.05.018

    55. [55]

      Faria, J. V.; dos Santos, M. S.; Bernardino, A. M. R.; Becker, K. M.; Machado, G. M. C.; Rodrigues, R. F.; Canto-Cavalheiro, M. M.; Leon, L. L. Bioorg. Med. Chem. Lett. 2013, 23, 6310.  doi: 10.1016/j.bmcl.2013.09.062

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