Skip to main content
SpringerLink
Log in

Discovery and synthesis of novel allylthioaralkylthiopyridazines: their antiproliferative activity against MCF-7 and Hep3B cells

  • Research Article
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Graphical Abstract

.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Abouzid, K.A.M., N.A. Khalil, E.M. Ahmed, and K.O. Mohamed. 2013. 3-[(6-Arylamino)pyridazinylamino]benzoic acids: design, synthesis and in vitro evaluation of anticancer activity. Archives of Pharmacal Research 36: 41–50.

    Article  CAS  PubMed  Google Scholar 

  • Agarwal, K.C. 1996. Therapeutic actions of garlic constituents. Medicinal Research Reviews 16: 111–124.

    Article  CAS  PubMed  Google Scholar 

  • Block, E., S. Ahmad, J.L. Catalfamo, M.K. Jain, and R. Apitz-Castro. 1986. Antithrombotic organosulfur compounds from garlic: Structural, mechanistic and synthetic studies. Journal of American Chemistry Society 108: 7045–7055.

    Article  CAS  Google Scholar 

  • Block, E. 2010. Garlic and other alliums. The lore and the science, 214–223. Cambridge: RSC publishing.

    Google Scholar 

  • Brunton, L.L., B.A. Chabner, and B.C. Knollmann. 2011. Goodman & Gilman’s the pharmacological basis of therapeutics, 12th ed, 1694–1698. New York: McGraw-Hill.

    Google Scholar 

  • Cavallito, C.J., J.S. Buck, and C.M. Suter. 1944. Allicin, the antibacterial principle of Allium sativum. II. Determination of the chemical structure. Journal of American Chemistry Society 66: 1952–1954.

    Article  CAS  Google Scholar 

  • Cha, M.Y., K.O. Lee, S.J. Kang, Y.H. Jung, J.Y. Song, K.J. Choi, J.Y. Byun, G.S. Lee, S.B. Park, and M.S. Kim. 2012. Synthesis and biological evaluation epidermal growth factor receptor 1 (HER-1) and HER-2 tyrosinkinases. Journal of Medicinal Chemistry 55: 2846–2857.

    Article  CAS  PubMed  Google Scholar 

  • Jung, J.H., E.J. Kim, H.K. Chung, H.J. Park, S.Y. Jeong, and E.K. Choi. 2012. c-Myc down-regulation is involved in proteasome inhibitor-mediated enhancement of radiotherapeutic efficacy in non-small cell lung cancer. International Journal of Oncology 40: 385–390.

    CAS  PubMed  Google Scholar 

  • Jung, M.Y., S.K. Kwon, and A. Moon. 2001. Chemopreventive allylthiopyridazine derivatives induce apoptosis in SK-Hep-1 hepatocarcinoma cells through a caspase-3-dependent mechanism. European Journal of Cancer 37: 2104–2110.

    Article  CAS  PubMed  Google Scholar 

  • Kleemann, A., and J. Engel. 2001. Pharmaceutical substances, 4th ed, 1340–1342. New York: Thieme.

    Google Scholar 

  • Kim, C.W., E.H. Park, and M.S. Park. 2013. Novel alkylaminopyridazine derivatives: Synthesis and their anti-proliferative effects against MCF-7 cells. Bulletin of the Korean Chemical Society 34(11): 3317–3321.

    Article  CAS  Google Scholar 

  • Kwon, S.K. 2002a. Synthesis of 4,5-substituted 3-alkoxy-6-allylthio-pyridazine derivatives. Yakhak Hoeji 46: 155–160.

    CAS  Google Scholar 

  • Kwon, S.K. 2002b. Synthesis of aryloxyallylthiopyridazine derivatives. Yakhak Hoeji 46: 89–92.

    CAS  Google Scholar 

  • Kwon, S.K., and M.S. Lee. 2005. Synthesis of 3-allylthio-6-heterocyclylalkylaminopyridazine derivatives and their anti-tumor activities against SK-Hep-1 human liver cancer cells. Yakhak Hoeji 49(6): 505–510.

    CAS  Google Scholar 

  • Kwon, S.K., and A. Moon. 2005. Synthesis of 3-alkylthio-6-allylthio-pyridazine derivatives and their antihepatocarcinoma activity. Archives of Pharmacal Research 28: 391–394.

    Article  CAS  PubMed  Google Scholar 

  • Lee, E.J., I.C. Shin, S.K. Kwon, H.S. Shin, and A. Moon. 2003. Chemopreventive allylthiopyridazines inhibit invasion, migration and angiogenesis in hepatocarcinoma cells. International Journal of Oncology 23: 1645–1650.

    CAS  PubMed  Google Scholar 

  • Lee, J.I., H. Park, Y.S. Yun, and S.K. Kwon. 2001. An efficient synthesis of 3-alkoxy-6-allylthiopyridazines. Journal of the Korean Chemical Society 45: 386–390.

    CAS  Google Scholar 

  • Lee, M.S., E.S. Kim, A. Moon, and M.S. Park. 2009. Synthesis of novel allylthio heterocyclo (or aryl) alkylaminopyridazines and their anticancer activity against SK-Hep-1 Cells. Bulletin of the Korean Chemical Society 30: 83–91.

    Article  CAS  Google Scholar 

  • Lee, S.H., and M.S. Park. 2011. New organoselenium compounds; synthesis of potential anticancer alkylselenoallylthiopyridazine derivatives. Yakhak Hoeji 55: 32–38.

    CAS  Google Scholar 

  • Park, E.H., and M.S. Park. 2005. Acylation of pyridazinylamines by acyclic anhydrides; synthesis of N-substituted 3-amino-6-chloropyridazines. Yakhak Hoeji 49(1): 56–59.

    CAS  Google Scholar 

  • Park, E.H., and M.S. Park. 2007. Synthesis of potential anticancer 6-allylthio-3-aminopyridazine derivatives. Journal of the Korean Chemical Society 51(3): 244–250.

    Article  CAS  Google Scholar 

  • Shin, H.S., and S.K. Kwon. 2003. Synthesis of allylthiopyridazine derivatives and inhibition of aflatoxin B1-induced hepatotoxicity in rats. Archives of Pharmacal Research 26: 351–357.

    Article  CAS  PubMed  Google Scholar 

  • Shukla, Y., and N. Kalra. 2007. Cancer chemoprevention with garlic and its constituents. Cancer Letters 247: 167–181.

    Article  CAS  PubMed  Google Scholar 

  • Song, J.H., S.G. Kim, Z.S. No, Y.L. Hyun, D.J. Jeon, and I. Kim. 2008. Discovery and synthesis of novel N-cyanopyrazolidine and N-cyanohexahydropyridazine derivatives as cathepsin inhibitors. Bulletin of the Korean Chemical Society 29: 1467–1471.

    Article  CAS  Google Scholar 

  • Tisler, M., and B. Stanovnik. 1984. Advances in heterocyclic chemistry. Katritzky & Boulton 3: 1–56.

    Google Scholar 

  • Won, Y.H., and M.S. Park. 2010. Synthesis and anticancer activities of new 3-allylthio-6-(mono or disubstituted) aminopyridazines. Archives of Pharmacal Research 33: 189–196.

    Article  CAS  PubMed  Google Scholar 

  • Yamasaki, T., R.W. Teel, and B.H. Lau. 1991. Effect of allicin, a phytoalexin produced by garlic, on mutagenesis, DNA-binding and metabolism of aflatoxin B1. Cancer Letters 59: 89–94.

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (No 2012050022). We would like to acknowledge Professor Joohee Jung (College of Pharmacy, Duksung Women’s University) for the CCK-8 assays of antiproliferative activities.

Author information

Authors and Affiliations

  1. College of Pharmacy, Duksung Women’s University, Seoul, 132-714, Korea

    Hae-Sun Park, Chaewon Kim & Myung-Sook Park

Authors
  1. Hae-Sun Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chaewon Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Myung-Sook Park
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Myung-Sook Park.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Park, HS., Kim, C. & Park, MS. Discovery and synthesis of novel allylthioaralkylthiopyridazines: their antiproliferative activity against MCF-7 and Hep3B cells. Arch. Pharm. Res. 38, 791–800 (2015). https://doi.org/10.1007/s12272-014-0416-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-014-0416-3

Keywords

Search

Navigation