Browse > Article
http://dx.doi.org/10.5012/bkcs.2011.32.8.3009

Importance of Imidazolidinone Motif in 4-Phenyl-N-arylsulfonylimidazolidinone for their Anticancer Activity  

Sharma, Vinay K. (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)
Joo, Cheon-Ik (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)
Jung, Sang-Hun (College of Pharmacy and Institute of Drug Research and Development, Chungnam National University)
Publication Information
Abstract
To investigate the possible isosteric replacement of imidazolidinone moiety in 4-phenyl-N-arylsulfonylimidazolidinone for broad and potent anticancer agents, a series of 4-phenyl-l(N)-arylsulfonylimidazolidinones 6a-k, imidazolidinethione analogs 7a-i, and imidazolidine oxime analogs 8a-c were prepared and evaluated for their in vitro anticancer activity against four human cancer cell lines (human lung A549, human colon COLO205, human leukemia K562, human ovary SK-OV-3). Among all the derivatives of N-arylsulfonylimidazolidinone 6a-k, compounds 6f and 6g showed the best inhibition comparable to doxorubicin against all cancer cell lines. Increasing the carbon chain on alkyl moieties of carbamates as shown in 6c-g did not alter the activity. The imidazolidinethione analogs 7a-i and imidazolidin-2-one oxime derivatives 8a-c did not possess any good activity. Therefore, imidazolidinone moiety is the best pharmacophore among the 4-phenyl-Narylsulfonylimidazolidinone derivatives.
Keywords
Arylsulfonylimidazolone; Anticancer activity; Antimitotic agent;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Rubinstein, L. V.; Shoemaker, R, H.; Paull, K. D.; Simon, R. M.; Toshini, S.; Skehan, P.; Scudiero, D. A.; Monks, A.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 113.
2 Skehan, P.; Storeng, R.; Scudiero, D. A.; Monks, A.; McMahon, J.; Vistica, D. T.; Warren, J. T.; Bokesch, H.; Kenny, F.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1107.   DOI
3 Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. In the Purification of Laboratory Chemicals, 2nd ed.; Pergamon Press: Oxford, England, 1982.
4 Lee, H. -S.; Park, K. -L.; Choi, S. -U.; Lee, C. -O.; Jung, S.-H. Arch. Pharm. Res. 2000, 23, 579.   DOI
5 Jung, S.-H.; Song, J.-S.; Lee, H.-S.; Choi, S.-U.; Lee, C.-O. Arch. Pharm. Res. 1996, 19, 570.   DOI
6 Jung, S.-H.; Song, J.-S.; Lee, H.-S.; Choi, S.-U.; Lee, C.-O. Bioorg. Med. Chem. Lett. 1996, 6, 2553.   DOI
7 Jung, S.-H.; Kwak, S.-J. Arch. Pharm. Res. 1997, 20, 283.   DOI
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.Bioorg.Med. Chem. Lett. 1998, 8, 1547.   DOI
9 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.; Jung, S. -H. U.S patent 592910327, 1999.
10 Jung, S.-H.; Park, K.-L.; Lee, H.-S.; Whang, J.-S. Arch. Pharm. Res. 2001, 24,499   DOI
11 Kim, I.-W.; Jung, S.-H. Arch. Pharm. Res. 2002, 25, 421.   DOI
12 Park Choo, H.-Y.; Choi, S.; Jung, S. -H.; Koh, H. -Y.; Pae, A. -N. Bioorg. Med. Chem. 2003, 11, 4585.   DOI
13 Kim, I.-W.; Lee, C.-K.; Kim, H.-S.; Jung, S.-H. Arch. Pharm. Res. 2003, 26, 9.   DOI
14 Jung, S.-H.; Lee, H.-S.; Kim, N.-S.; Kim, H. -M.; Lee, M.; Choi, D.-R.; Lee, J.-A.; Chung, Y.-H.; Moon, E. -Y.; Hwang, H.-S.; Seong, S.-K.; Lee, D.-K. Arch. Pharm. Res. 2004, 27, 478.   DOI
15 Lee, C. W.; Hong, D. H.; Han, S. B.; Jung, S. -H.; Kim, H. C.;Fine R.L.; lee, S. -H.; Kim, H. M. Biochem. Pharmacol. 2002, 64, 473.   DOI   ScienceOn
16 Yoshimatsu, K.; Yamaguchi, A.; Yoshino, H.; Koyanagi, N.; Kitoh, K. Cancer Res. 1997, 57, 3208.
17 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.; Jung, S. -H. Bioorg. Med. Chem. Lett. 2004, 14, 6075.   DOI
18 Yoshino, H.; Ueda, N.; Nijima, J.; Sugumi, H.; Kotake, Y.; Koyanagi, N.; Yoshimatsu, K.; Asada, M.; Watanabe, T.; Nagaau, T.; Tsukahara, K.; Iijima, A.; Kitoh, K. J. Med. Chem. 1992, 35, 2496.   DOI
19 Koyanagi, N.; Nagasu, T.; Fujita, F.; Watanabe, T.; Tsukahara, K.; Funahashi, Y.; Fujita, M.; Taguchi, T.; Yoshino, H.; Kitoh, K. Cancer Res. 1994, 54, 1702.
20 Owa, T.; Yoshino, H.; Okauchi, T.; Yoshimatsu, K.; Ozawa, Y.; Sugi, N. H.; Nagasu, T.; Koyanagi, N.; Kitoh, K. J. Med. Chem.1999, 42, 3789.   DOI
21 Hideki Tanaka, H.; Ohshima, N.; Ikenoya, M.; Komori, K.; Katoh, F.; Hidaka, H. Cancer Res. 2003, 63, 6942.
22 Takagi, M.; Honmura, T.; Watanabe, S.; Yamaguchi, R.; Nogawa, M.; Nishimura, I.; Katoh, F.; Matsuda, M.; Hidaka, H. Invest. New Drugs 2003, 21, 387.   DOI
23 DiMaio, M. A.; Mikhailov, A.; Rieder, C. L.; Von Hoff, D. D.; Palazzo, R. E. Mol. Cancer Ther. 2009, 8, 592.   DOI
24 Mauer, A. M.; Cohen, E. E.; Ma, P. C.; Kozloff, M. F.; Schwartzberg, L.; Coates, A. I.; Qian, J.; Hagey, A. E.; Gordon, G. B. J. Thorac. Oncol. 2008, 3, 631.   DOI
25 Fox, E.; Maris, J. M.; Widemann, B. C.; Goodspeed, W.; Goodwin, A.; Kromplewski, M.; Fouts, M. E.; Medina, D.; Cohn, S. L.; Krivoshik, A.; Hagey, A. E.; Adamson, P. C.; Balis, F. M. Clin. Cancer Res. 2008, 14, 1111.   DOI
26 Zandvliet, A. S.; Schellens, J. H. M.; Dittrich, C.; Wanders, J.; Beijnen, J. H.; Huitema, A. D. R. Br. J. Clin. Pharmacol. 2008, 66, 485.   DOI
27 Mahindroo, N.; Liou, J.-P.; Chang, J.-Y.; Hsieh, H.-P. Expert Opin. Ther. Patents 2006, 16, 647.   DOI
28 Siegel-Lakhai, W. S.; Zandvliet, A. S.; Huitema, A. D. R.; Tibben, M. M.; Milano, G.; Girre, V.; Dieras, V.; King, A.; Richmond, E.; Wanders, J.; Beijnen, J. H.; Schellens, J. H. M. Brit. J. Cancer 2008, 98, 1320.   DOI
29 Garland, L. L.; Taylor, C.; Pilkington, D. L.; Cohen, J. L.; Von Hoff, D. D. Clin. Cancer Res. 2006, 12, 5182.   DOI
30 Jordan, M. A.; Wilson, L. Nat. Rev. Cancer 2004, 4, 253.   DOI
31 Sridhare, M.; Macapinlac, M. J.; Goel, S.; Verdier-Pinard, D.; Fojo, T.; Rothenberg, M.; Colevas, D. Anticancer Drugs 2004, 15, 553.   DOI
32 Davis, P. D.; Dougherty, G. J.; Blakey, D. C.; Galbraith, S. M.; Tozer, G. M.; Holder, A. L.; Naylor, M. A.; Nolan, J.; Stratford, M. R. L.; Chaplin, D. J.; Hill, S. A. Cancer Res. 2002, 62, 7247.
33 Jordan, M. A.; Wilson, L. Nat. Rev. Cancer 2004, 4, 253.   DOI
34 Mealy, N. E.; Balcells, L. M. Drugs Future 2006, 31, 541.