Skip to main content
Log in

Recognition of the importance of imidazolidinone motif for cytotoxicity of 4-phenyl-1-arylsulfonylimidazolidinones using thiadiazolidine-1,1 -dioxide analogs

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

Abstract

For probing the importance of planarity of imidazolidinone motif of 4-phenyl-1-(N-acylindoline-5-sulfonyl)imidazolidinones1 for their cytotoxicity, 4-phenyl-1-(N-acylindoline-5-sulfonyl)[1,2,5]thiadiazolidine-1,1-dioxides2 were prepared and their cytotoxicity were measured against human lung carcinoma (A549), human colon carcinoma (COLO205), human ovarian cancer (SK-OV-3), human leukemic cancer (K562), and murine colon adenocarcinoma (Colon26) cell linesin vitro. Although only carbonyl moiety of imidazolidinone ring was replaced with sulfonyl group, compounds2 do not show any activity against all five cancer cell lines unlike 1. Therefore the planarity of imidazolidinone ring of1 should be an important factor for their cytotoxic activity.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Abiko, A. and Masammune, S., An improved, convenient procedure for the reduction of amino acids to aminoalcohols: Use of NaBH4-H2SO4.Tetrahedron Lett., 33, 5517–5518 (1992).

    Article  CAS  Google Scholar 

  • DeBois, G. E., Amination of arylsulfamate esters. A convenient general synthesis of aliphatic sulfamide.J. Org. Chem., 45, 5373–5375 (1980).

    Article  Google Scholar 

  • Everitt, E., Wohlfart, C., Spectrometric quantitation of anchorage-dependent cell numbers extraction of naphthol blue-black-stained cellular protein.Anal. Biochem., 162, 122–129 (1987).

    Article  PubMed  CAS  Google Scholar 

  • Hwang, H.-S., Moon, E.-Y., Seong, S.-K., Choi, C.-H., Chung, C.-H., Jung, S.-H., Yoon, S.-J., Characterization of the anticancer activity of DW2282, a new anticancer agent. Anticancer Res., 19, 5087–5093 (1999).

    PubMed  CAS  Google Scholar 

  • Jung, S.-H., Song, J.-S., Lee, H.-S., Choi, S.-U., Lee, C.-O., Synthesis and evaluation of cytotoxicity of novel arylsulfonylimidazolidinones containing sulfonylurea pharmacophore.Arch. Pharm. Res., 19, 570–580 (1996).

    CAS  Google Scholar 

  • Jung, S.-H., Song, J.-S., Lee, H.-S., Choi, S.-U., Lee, C.-O., Synthesis and evaluation of cytotoxic activity of novel arylsulfonylimidazolidinones.Bioorg. & Med. Chem. Letters, 6, 2553–2558 (1996).

    Article  CAS  Google Scholar 

  • Jung, S.-H., Kwak, S.-J., Planar structural requirement at 4-position of 1-arylsulfonyl-4-phenyl-4,5-dihydro-2-imidazolones for their cytotoxicity.Arch. Pharm. Res., 20, 283–287 (1997).

    Article  CAS  PubMed  Google Scholar 

  • Jung, S.-H., Lee, H.-S., Song, J.-S., Kim, H.-M., Han, S.-B., Lee, C.-W., Lee, M., Choi, D.-R., Lee, J.-A., Chung, Y.-H., Yoon, S.-J., Moon, E.-Y., Hwang, H.-S., Seong, S.-K., Lee, D.-K., Synthesis and antitumor activity of 4-phenyl-1-arylsulfonylimidazolidinones.Bioorg. & Med. Chem. Letters, 8, 2553–2558 (1997).

    Google Scholar 

  • Jung, S.-H., Kwak, S.-J., Kim, N.-D., Lee, S.-U., Lee, C.-O., Stereochemical Requirement at 4-Position of 4-Phenyl-1-arylsulfonylimidazolidinones for their Cytotoxicities.Arch. Pharm. Res., 23, 35–41 (2000).

    Article  PubMed  CAS  Google Scholar 

  • Lee, C.-H., Song, J.-S., Lee, Y.-H., Choi, W.-S., Chung, B.-Y., A convenient synthesis of N-alkyl-N'-(l-caroalkoxyalkyl) sulfamides.Bull. Korean Chem. Soc., 14, 762–764 (1993).

    CAS  Google Scholar 

  • Lee, H.-S., Park, K.-L., Choi, S.-H., Lee, C.-O., and Jung, S.-H., Effect of substituents on Benzenesulfonyl Motif of 4-phenyl-1-arylsulfonylimidazolidinones for their cytotoxicity.Arch. Pharm. Res., 23, 579–584 (2000).

    Article  PubMed  Google Scholar 

  • Park, K.-L., Moon, B.-G., Jung, S.-H., Kim, J.-G., Suh, l.-H., Multicenter Hydrogen Bonds in a 2:1 arylsulfonylimidazolone hydrochloride salt.Acta Crystallography, C56, 1247–1250 (2000).

    Article  CAS  Google Scholar 

  • Perrin, D. D., Armarego, W. L. F., and Perrin, D. R.,Purification of laboratory chemicals, 2nd edition. Pergamon Press, Oxford, England, (1982).

    Google Scholar 

  • Skehan, P., Storeng, R., Scudiero, D. A., Monks, A., MacMahon, J., Vista, D. T., Kenny, S., Boyd, M. R. New colorimetric cytotoxicity assay for anticancer drug screening.J. Natl. Cancer Inst., 82, 1107–1112 (1990).

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Sang-Hun Jung.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kim, IW., Jung, SH. Recognition of the importance of imidazolidinone motif for cytotoxicity of 4-phenyl-1-arylsulfonylimidazolidinones using thiadiazolidine-1,1 -dioxide analogs. Arch Pharm Res 25, 421–427 (2002). https://doi.org/10.1007/BF02976594

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02976594

Key words

Navigation