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Evaluation of Anticancer Activity of 4-Vinyl-1-Arylsulfonylimidazolidinones  

Kwak, Son-Hyok (College of Pharmacy, Chungnam National University)
Bang, Seong-Cheol (College of Pharmacy, Chungnam National University)
Seo, Hyun-Hee (College of Pharmacy, Chungnam National University)
Shin, Hye-Rim (College of Pharmacy, Chungnam National University)
Lee, Ki-Cheul (College of Pharmacy, Chungnam National University)
Hoang, Le Tuan Anh (College of Pharmacy, Chungnam National University)
Jung, Sang-Hun (College of Pharmacy, Chungnam National University)
Publication Information
Archives of Pharmacal Research / v.29, no.9, 2006 , pp. 721-727 More about this Journal
Abstract
To continue exploration of structure activity relationship of novel 1-(indoline-5-sulfonyl)-4-phenylimidazolidinones (1) reported as anticancer agent with broad spectrum, three 1-(arylsulfonyl)-4-vinylimidazolidinones (2) were synthesized from methyl serinate (3) in 8 steps. Reaction of intermediate 2-phenoxycarbonylaminobut-3-enyl p-toluenesulfonate (10) with arylsulfonamide in the presence of potassium carbonate produced corresponding 2 and N-(4-vinyloxazolidin-2-yl)arylsulfonamide 11 in approximately equal ratio. This reaction is believed to undergo through urea intermediate 16 as shown in scheme 3. 1-Arylsufonyl-4-vinylimidazolidinones 2 show much reduced activity against human colon carcinoma (Colo205), human chronic myelogenous leukemia (K562), and human ovarian adenocarcinoma (SK-OV-3) and compatible activity against human lung carcinoma (A549) compared to 1. Therefore phenyl at 4-position should be the optimum planar motif for the activity of 1.
Keywords
Synthesis and cytotoxicity of 1-arylsulfonyl-4-vinylimidazolidinones;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 3  (Related Records In Web of Science)
Times Cited By SCOPUS : 3
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1 Jung, S.-H., Song, J.-S., Lee, H.-S., Choi, S.-U., and Lee, C.-O., Synthesis and evaluation of cytotoxic activity of novel arylsulfonylimidazolidinones. Bioorg. & Med. Chem. Lett., 6, 2553-2558 (1996)   DOI   ScienceOn
2 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., and Lee, D.-K., Synthesis and antitumor activity of 4-phenyl-1- arylsulfonylimidazolidinones, Bioorg. & Med. Chem. Lett., 8, 2553-2558 (1998)
3 Jung, S.-H., Park, K.-L., Lee, H.-S., and Whang, J.-S. Evaluation of the role of imidazolidinone motif of Antineoplastic 4- phenyl-1-arylsulfonylimidazolidinones using 4-phenyl-2-arylsulfonyloxazolines, Arch. Pharm. Res., 24, 499-502 (2001)   DOI   ScienceOn
4 Kim, I.-W., Lee, C.-K., Kim, H.-S., and Jung, S.-H., Importance of sulfonylimidazolidinone motif of 4-phenyl-1-arylsulfonylimidazolidinones for their cytotoxicity: Synthesis of 2-benzoyl- 4-phenyl[1,2,5]thiazolidine-1,1-dioxides and their cytotoxicity, Arch. Pharm. Res., 26, 9-14 (2003)   DOI
5 Jung, S.-H. and 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)   DOI   ScienceOn
6 Jung, S. H., Kwak, S. J., Kim, N. D., Lee, S. U., and Lee, C. O., Stereochemical requirement of 4-phenyl-1-arylsulfonylimidazolidinones for their cytotoxicities, Arch. Pharm. Res., 23, 35- 41 (2000)   DOI   ScienceOn
7 Lee, H.-S., Park, K.-L., Choi, S.-U., 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)   DOI   ScienceOn
8 Lee, C. H., Hong, D. H., Han, S. B., Jung, S.-H., Kim, H. C., Fine R. L., Lee, S.-H., and Kim, H. M., A novel stereo-selective sulfonylurea, 1-[1-(4-aminobenzoyl)-2,3-dihydro-1H-indol-6- sulfonyl]-4-phenyl-imidazolidin-2-one, has antitumor efficacy in in vitro and in vivo tumor models, Biochemical Pharmacology, 64, 473-480 (2002)   DOI   ScienceOn
9 Scudiero, D. A., Shoemaker, R. H., Paull, K. D., Monk, A., Tierney, S., Nofziger, T. M., Seniff, D., and Boyd, M. R., Evaluation of a soluble tetrazoliun/formazan assay for cell growth: a sensitivity in culture using human and other tumor cell line, Cancer Res., 48, 4827-4833 (1988)
10 Ganer, P. and Park, J. M., The synthesis and configurational stability of differentially protected ${\beta}$-hydroxy-${\alpha}$-amino aldehydes, J. Org. Chem., 52, 2361-2364 (1987)   DOI
11 Moriwake, T., Hamano, S., Saito, S., and Torii, S., A straightforward synthesis of allyl amines from ${\alpha}$-amino acids without racemization, Chem. Lett., 2085-2088 (1987)
12 Moon, E.-Y., Seong, S.-K., Jung, S.-H., Lee, M., Lee, D.-K. Rhee, D.-K., Pyo, S., and Yoon, S.-J., Antitumor Activity of 4- Phenyl-1-arylsulfonylimidazolidinone, DW2143, Cancer Letters, 140, 177-187 (1999)   DOI   ScienceOn
13 Kim, S., Park, J. H., Koo, S. Y., Kim, J. I., Kim, M. H., Kim, E. J., Jo, K., Choi, H. G., Lee, S. B., and Jung, S. H., Novel diarylsulfonylurea derivatives as potent antimitotic agents, Bioorg. Med. Chem. Lett., 14, 6075-6078 (2004)   DOI   ScienceOn
14 Williams, L., Zhang, Z., Shao, F., Carroll, P. J., and Joullie, M. M., Grignard reactions to chiral oxazolidine aldehydes, Tetrahedron, 36, 11673-11694 (1996)
15 Yoon, S. J., Chung, Y. H., Lee, M. S., Choi, D. R., Lee, J. A., Lee, H. S., Yun, H. R., Lee, D. K., Moon, E. Y., Hwang, H. S., Choi, C. H., and Jung, S. H., Arylsulfonylimidazolone Derivatives As An Antitumor Agent, WO 98/07719, PCT/KR 97/00154 (1998)
16 Jung, S.-H., Lee, H.-S., Song, J.-S., Kim, N. -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., and Lee, D.-K., Synthesis and cytotoxic activity of 1(1- benzoylindoline-5-sulfonyl)-4-phenylimidazolidinones, Arch. Pharm. Res., 2004, 478-484
17 Choo Park, H.-Y., Choi, S., Jung, S. H., Koh, H. Y., and Pae, A. N., The 3D-QSAR study of antitumor arylsulfonylimidazolidinone derivatives by CoMFA and CoMSIA, Bioorg. Med. Chem., 11, 4585-4589 (2003)   DOI   ScienceOn
18 Perrin, D. D., Armarego, W. L. F., and Perrin, D. R., Purification of laboratory chemicals, 2nd edition. Pergamon Press, Oxford, England, (1982)
19 Jung, S.-H., Song, J.-S., Lee, H.-S., Choi, S.-U., and Lee, C.-O., Synthesis and evaluation of cytotoxicity of novel arylsulfonylimidazolidinones containing sulfonylurea pharmacophore. Arch. Pharm. Res., 19, 570-580 (1996)   DOI