Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
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Recognition of the Importance of Imidazolidinone Motif for Cytotoxicity of 4-Phenyl-1-arylsulfonylimidazolidinones Using Thiadiazolidine-1, 1-Dioxide Analogs

  • Kim, Il-Whan (College of Pharmacy, Chungnam National University) ;
  • Jung, Sang-Hun (College of Pharmacy, Chungnam National University)
  • Published : 2002.08.01
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Abstract

For probing the importance of planarity of imidazolidinone motif of 4-phenyl-1-(N-acylindoline-5-sulfonyl)imidazolidinones 1 for their cytotoxicity, 4-phenyl-1-(N-acylindoline-5-sulfonyl)[1,2,5]thiadiazolidine-1,1-dioxides 2 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 lines in vitro. Although only carbonyl moiety of imidazolidinone ring was replaced with sulfonyl group, compounds 2 do not show any activity against all five cancer cell lines unlike 1. Therefore the planarity of imidazolidinone ring of 1 should be an important factor for their cytotoxic activity.

Keywords

References

  1. Abiko, A. and Masammune, S., An improved, convenient procedure for the reduction of amino acids to aminoalcohols: Use of $NaBH_4-H_2SO_4$. Tetrahedron Lett., 33, 5517-5518 (1992) https://doi.org/10.1016/S0040-4039(00)61133-4
  2. DeBois, G. E., Amination of arylsulfamate esters. A convenient general synthesis of aliphatic sulfamide. J. Org. Chem., 45, 5373-5375 (1980) https://doi.org/10.1021/jo01314a034
  3. 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) https://doi.org/10.1016/0003-2697(87)90016-9
  4. 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. Anicancer Res., 19, 5087-5093 (1999)
  5. 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) https://doi.org/10.1007/BF02986031
  6. Jung, S.-H., Song, J.-S., Lee, H.-S., Choi, S.-U., Lee, C.-O., Svnthesls and evaluation of cytotoxic activity of novel arylsulfonylimidazolidinones. Bioorg. & Med. Chem. Letters, 6, 2553-2558 (1996) https://doi.org/10.1016/0960-894X(96)00463-5
  7. 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) https://doi.org/10.1007/BF02976159
  8. 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-aryIsulfonylimidazolidinones. Bioorg. & Med. Chem. Letters, 8, 2553-2558 (1997)
  9. Junq, 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) https://doi.org/10.1007/BF02976463
  10. Lee, C.-H., Song, J.-S., Lee., Y.-H., Choi., W.-S., Chung, B.-Y., A convenient synthesis of N-alkyl-N'-(1-caroalkoxyalkyl) sulfamides. Bull. Korean Chem. Soc., 14, 762-764 (1993)
  11. 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) https://doi.org/10.1007/BF02975244
  12. Park, K.-L., Moon, B.-G., Jung, S.-H., Kim, J.-G., Suh, I.-H., Multicenter Hydrogen Bonds in a 2:1 arylsulfonylimidazolone hydrochloride salt. Acta Crystallography, C56, 1247-1250 (2000)
  13. Perrin, D. D., Armarego, W. L. F., and Perrin, D. R., Purification of laboratory chemicals, 2nd edition. Pergamon Press, Oxford, England, (1982)
  14. 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) https://doi.org/10.1093/jnci/82.13.1107