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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 Cytotoxcity  

Kim, Il-Whan (College of Pharmacy, Chungnam National University)
Lee, Chong-Kyo (Korea Research Institute of Chemical Technology)
Kim, Hae-Soo (Korea Research Institute of Chemical Technology)
Jung, Sang-Hun (College of Pharmacy, Chungnam National University)
Publication Information
Archives of Pharmacal Research / v.26, no.1, 2003 , pp. 9-14 More about this Journal
Abstract
For probing the importance of planarity of imidazolidinone motif of 4-phenyl-1-(benzenesulfonyl)imidazolidinones 1 for their cytotoxicity, 4-phenyl-2-(benzoyl)[1,2,5]thiadiazolidine-1,1-dioxide (2a), 4-phenyl-2-(p-toluoyl)[1,2,5]thiadiazolidine-1,1-dioxide (2b), 4-phenyl-2-(phenylcarbamoyl)[1,2,5]thiadiazolidine-1,1-dioxide (3a), and 4-phenyl-2-(p-tolylcarbamoyl)[1,2,5]thiadiazolidine-1,1-dioxide (3b) were prepared along with their regioisomers (5a, 5b, 9a, 9b) 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. All compounds prepared do not show any activity against all five cancer cell lines unlike 1. Compounds 1 possess planarity of imidazolidinone, especially in sulfonylurea moiety ($-SO_2$NHCONH-). However compounds 2 and 3 have nonplanar 5-membered ring, [1,2,5]thiadiazolidine-1,1-dioxides. Such structural differentiation might result in the loss of activity. Therefore the inactivity of 2 and 3 could also be an indication for the necessity of planarity of imidazolidinone ring of 1 for their cytotoxic activity.
Keywords
(Benzenesulfonyl)-4-Phenyl-1-imidazolidinones; Cytotoxicity; 2-(Benzoyl)-4-phenyl-[1,2,5]thiadiazolidine-1,1-dioxides;
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Times Cited By Web Of Science : 12  (Related Records In Web of Science)
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1 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)   DOI   ScienceOn
2 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)   DOI   ScienceOn
3 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)   DOI   ScienceOn
4 Perrin, D. D., Armarego, W. L. F., and Perrin, D. R., Purification of laboratory chemicals, 2nd edition. Pergamon Press, Oxford, England, (1982)
5 Everitt, E., Wohlfart, C., Spectrometric quantitation of anchoragedependent cell numbers extraction of naphthol blue-blackstained cellular protein. Anal. Biochem., 162, 122-129 (1987)   DOI   ScienceOn
6 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)   DOI   ScienceOn
7 Howbert, J. J., Grossman, C. S., Crowell, T. A., Rieder, B. J., Harper, R. W., Kramer, K. E., Tao, E. V., Aikins, J., Poore, G. A., Rinzel, S. M., Grindey, G. B., Shaw, W. N., Todd, G. C., Novel Agents Effective against Solid Tumors: The Diarylsulfonylureas. Synthesis, Activities, and Analysis of Quantitative Structure-Activity Relationships. J. Med. Chem., 33, 2393-2407 (1990)   DOI   PUBMED
8 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., 1999, 19, 5087-5093   PUBMED
9 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)   DOI   ScienceOn
10 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)
11 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)   DOI   PUBMED
12 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)