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Synthesis, preliminary structure-activity relationships and biological evaluation of pyridinyl-4,5-2H-isoxazole derivatives as potent antitumor agents

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Abstract

A series of novel pyridinyl-4,5-2H-isoxazole derivatives was synthesized and their chemical structures were characterized by 1H NMR, 13C NMR as well as MS spectroscopic methods, their melting points were also determined. The inhibitory effects of them against breast cancer cell line(MCF-7) were evaluated by 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide(MTT) procedure in vitro. Most of them possesed potent anti-proliferative activities, among which 11c and 11j exhibited half maximal inhibitory concentrations(IC50) of 1.9 and 1.5 μmol/L, respectively. These compounds also exhibited potent anti-proliferative activities against both human hepatoma cell line(HepG2) and cervical cancer cell line(Hela). Preliminary Structure-activity relationship(SAR) information from these compounds can be used to guide further exploration of new compounds with better potency as molecular probes. Further study on the mechanism-of-action of these compounds is under investigation.

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References

  1. Devita V. T., Rosenberg S. A., N. Engl. J. Med., 2012, 366(23), 2207

    Article  CAS  Google Scholar 

  2. Daly J. M., Weintraub F. N., Shou J., Rosato E. F., Lucia M., Ann. Surg., 1995, 221(4), 327

    Article  CAS  Google Scholar 

  3. Kaliberov S. A., Buchsbaum D. J., Cancer Res., 2012, 115, 221

    Article  CAS  Google Scholar 

  4. Gerber D. E., Schiller J. H., J. Clin. Oncol., 2013, 31(8), 1009

    Article  CAS  Google Scholar 

  5. Zhang Y. H., Ye L. H., Peng H. Y., Zhang X., J. Nanjing Univ. Tradit. Chin. Med., 2011, 1, 4

    Google Scholar 

  6. Flaherty K. T., Clin. Cancer Res., 2006, 12(7), 2366

    Article  Google Scholar 

  7. Kim J., Lee J. E., Lee S. H., Yu J. H., Lee J. H., Park T. G., Hyeon T., Adv. Mater., 2008, 20(3), 478

    Article  CAS  Google Scholar 

  8. Demartino J. K., Boger D. L., Drug Future, 2008, 33(11), 969

    Article  CAS  Google Scholar 

  9. Ferlay J., Autier P., Boniol M., Heanue M., Colombet M., Boyle P., Ann. Oncol., 2007, 18(3), 581

    Article  CAS  Google Scholar 

  10. Nussbaumer S., Bonnabry P., Jean-Luc V., Fleury-Souverain S., Talanta, 2011, 85(5), 2265

    Article  CAS  Google Scholar 

  11. Jemal A., Siegel R., Ward E., Murray T., Xu J., Smigal C., Thun M. J., Cancer J. Clin., 2006, 56(2), 106

    Article  Google Scholar 

  12. Kaushik G., Kaushik T., Khanduja S., Pathak C. M., Khanduja K. L., Cancer Lett., 2008, 270(1), 120

    Article  CAS  Google Scholar 

  13. Bhuva H. A., Kini S. J., J. Mol. Graph. Model., 2010, 29(1), 32

    Article  CAS  Google Scholar 

  14. Albreht T., Mckee M., Alexe D. M., Coleman M. P., Martin-Moreno J. M., Eur. J. Cancer, 2008, 44(10), 1451

    Article  Google Scholar 

  15. Madhusudan S., Trivadi S., Ganesan T. S., Clinical. Biochem., 2004, 37, 618

    Article  CAS  Google Scholar 

  16. Sawyers C., Nature, 2004, 432(7015), 294

    Article  CAS  Google Scholar 

  17. Eckhardt S., Curr. Med. Chem. Anti-Cancer Agents, 2002, 2(3), 419

    Article  CAS  Google Scholar 

  18. Li Q. B., Xu W. F., Curr. Med. Chem. Anti-Cancer Agents, 2005, 5(1), 53

    Article  CAS  Google Scholar 

  19. Bagalkot V., Zhang L. F., Levy-Nissenbaum E., Jon S. Y., Kantoff P. W., Langer R., Farokhzad O. C., Nano Lett., 2007, 7(10), 3065

    Article  CAS  Google Scholar 

  20. Willmann J. K., Bruggen N. V., Dinkelborg L. M., Gambhir S. S., Nat. Rev. Drug Discov., 2008, 7(7), 591

    Article  CAS  Google Scholar 

  21. Dong B., Zhu Y. M., Chin. J. Cancer, 2010, 29(3), 340

    Article  Google Scholar 

  22. Yang H. L., Xu G. X., Bao M. Y., Zhang D. P., Li Z. W., Pei Y. Z., Chem. J. Chinese Universities, 2014, 35(12), 2584

    CAS  Google Scholar 

  23. Fanta P. E., J. Am. Chem. Soc., 1953, 75, 737

    Article  CAS  Google Scholar 

  24. Altmann E., Aichholz R., Betschart C., Buhl T., Green J., Irie O., Teno N., Lattmann R., Tintelnot-Blomley M., Missbach M., J. Med. Chem., 2007, 50(4), 591

    Article  CAS  Google Scholar 

  25. Rogez-Florent T., Meignan S., Foulon C., Six P., Gros A., Bal-Mahieu C., Supuran C. T., Scozzafava A., Frédérick R., Masereel B., Depreux P., Lansiaux A., Goossens J. F., Gluszok S., Goossens L., Bioorg. Med. Chem., 2013, 21(6), 1451

    Article  CAS  Google Scholar 

  26. Hartshorn M. J., Murray C. W., Cleasby A., Frederickson M., Tickle I. J., Jhoti H., J. Med. Chem., 2005, 48(2), 403

    Article  CAS  Google Scholar 

  27. Badrinarayan P., Sastry G. N., J. Chem. Inf. Model., 2011, 51(1), 115

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. College of Veterinary Medicine, Northeast Agricultural University, Harbin, 150030, P. R. China

    Hongliang Yang

  2. School of Pharmaceutical Sciences, Jilin University, Changchun, 130021, P. R. China

    Guoxing Xu & Yazhong Pei

Authors
  1. Hongliang Yang
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  2. Guoxing Xu
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  3. Yazhong Pei
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Corresponding author

Correspondence to Hongliang Yang.

Additional information

Supported by the Youth Natural Science Foundation of Heilongjiang Province, China(No.QC2016025).

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Yang, H., Xu, G. & Pei, Y. Synthesis, preliminary structure-activity relationships and biological evaluation of pyridinyl-4,5-2H-isoxazole derivatives as potent antitumor agents. Chem. Res. Chin. Univ. 33, 61–69 (2017). https://doi.org/10.1007/s40242-017-6330-8

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  • DOI: https://doi.org/10.1007/s40242-017-6330-8

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