Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Water Soluble Analogs of Arylsulfonylimidazolidinone (JSH-2282)

  • Bang, Seong-Cheol (College of Pharmacy and Institute of Drug Research and Development, Chungnam National University) ;
  • Lee, Ki-Cheul (College of Pharmacy and Institute of Drug Research and Development, Chungnam National University) ;
  • Sharma, Vinay K. (College of Pharmacy and Institute of Drug Research and Development, Chungnam National University) ;
  • Sharma, Niti (College of Pharmacy and Institute of Drug Research and Development, Chungnam National University) ;
  • Yang, Hyun-Sun (College of Pharmacy and Institute of Drug Research and Development, Chungnam National University) ;
  • Jung, Sang-Hun (College of Pharmacy and Institute of Drug Research and Development, Chungnam National University)
  • Received : 2013.02.06
  • Accepted : 2013.04.08
  • Published : 2013.07.20
Download PDF
⟨ Previous Next ⟩

Abstract

To improve the water solubility of arylsulfonylimidazolidinone (JSH-2282), a potent anti-cancer agent, two urea derivatives, sodium (S)-2-(3-(4-(5-((S)-2-oxo-4-phenylimidazolidin-1-ylsulfonyl)indoline-1-carbonyl)-phenyl)ureido)succinate (2a) and sodium (S)-2-(3-(4-(5-((S)-2-oxo-4-phenylimidazolidin-1-ylsulfonyl)indoline-1-carbonyl)phenyl)ureido)pentanedioate (2b), were synthesized and studied for solubility and anti-cancer activity.

Keywords

References

  1. Jordan, M. A.; Wilson, L. Nat. Rev. Cancer 2004, 4, 253. https://doi.org/10.1038/nrc1317
  2. Jordan, A.; Hadfield, J. A.; Lawrence, N. J.; McGown, A. T. Med. Res. Rev. 1998, 18, 259. https://doi.org/10.1002/(SICI)1098-1128(199807)18:4<259::AID-MED3>3.0.CO;2-U
  3. Lee, C. W.; Hong, D. H.; Han, S. B.; Jong, S.-H.; Kim, H. C.; Fine, R. L.; Lee, S.-H.; Kim, H. M. Biochem. Pharmacol. 2002, 64, 473. https://doi.org/10.1016/S0006-2952(02)01105-X
  4. Kim, S.; Park, J.-H.; Koo, S.-Y., Kim, J. I.; Kim, M.-H.; Kim, J. E.; Jo, K.; Choi, H. G.; Lee, S. B.; Jung, S.-H. J. Bioorg. Med. Chem. Lett. 2004, 4, 6075.
  5. Bundgaard, H. In A Textbook of Drug Design and Development; Larsen, P. K., Bundgaard, H., Eds.; Harwood Academic: Switzerland, 1982; pp 1-39.
  6. Bundgaard, H. Drugs of Fut. 1991, 16, 443.
  7. Kearney, A. S.; Stella, V. J. Pharm. Res. 1992, 9, 497. https://doi.org/10.1023/A:1015840329786
  8. Rose, W. C. Anticancer Drugs 1992, 3, 311. https://doi.org/10.1097/00001813-199208000-00001
  9. Safadi, M.; Oliyai, R.; Stella, V. J. Pharm. Res. 1993, 10, 1350. https://doi.org/10.1023/A:1018934200343
  10. Carey, F. A.; Giuliano, R. M. Organic Chemistry, 8th ed.; McGraw-Hill: 2010; pp 1134-1135.
  11. Goolcharran, C.; Khossravi, M.; Borchardt, R. T. In Pharmaceutical Formulation Development of Peptide and Proteins; Frokjaer, S., Hovgaard, L., Eds.; Taylor and Francis, London, 2000; pp 70-88.
  12. Casini, A.; Scozzafava, A.; Mincione, F.; Menabuoni, L.; Ilies, M. A.; Supuran, C. T. J. Med. Chem. 2000, 43, 4884. https://doi.org/10.1021/jm001051+
  13. http://webcache.googleusercontent.com/search?q=cache:VniKXVZiwgcJ:www.merckmanuals.com/professional/clinical_pharmacology/pharmacokinetics/drug_absorption.html.
  14. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesh, H.; Kenney, S.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1107. https://doi.org/10.1093/jnci/82.13.1107

Cited by

  1. ChemInform Abstract: Synthesis of Water Soluble Analogues of Arylsulfonylimidazolidinone (JSH-2282). vol.44, pp.43, 2013, https://doi.org/10.1002/chin.201343118