Synthesis and Cytotoxicity Evaluation of Some Novel 1-(3-Chlorophenyl)piperazin-2-one Derivatives Bearing Imidazole Bioisosteres
Saeed Ghasemi A , Simin Sharifi C D , Soodabeh Davaran A C D , Hosein Danafar A , Davoud Asgari A C and Javid Shahbazi Mojarrad A B E
+ Author Affiliations
- Author Affiliations
A Department of Medicinal Chemistry, Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz 51664, Iran.
B Tuberculosis and Lung Disease Research Center, Tabriz University of Medical Sciences, Tabriz 51664, Iran.
C Research Center for Pharmaceutical Nanotechnology, Tabriz University of Medical Sciences, Tabriz 51664, Iran.
D Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz 51664, Iran.
E Corresponding author. Email: jvshahbazi@yahoo.com
Australian Journal of Chemistry 66(6) 655-660 https://doi.org/10.1071/CH13031
Submitted: 19 January 2013 Accepted: 22 February 2013 Published: 25 March 2013
Abstract
A series of substituted 3-chlorophenylpiperazinone derivatives were synthesised using L-778123 (an imidazole-containing FTase inhibitor) as a model by bioisosteric replacement of the imidazole ring. The final compounds were evaluated against two human cancer cell lines including A549 (lung cancer) and HT-29 (colon cancer) by MTT assay. The results showed that substitution of imidazole ring with 1-amidinourea, semicarbazide, and thiobiuret led to improvement of cytotoxic activity against both cell lines.
References
[1] A. Aliabadi, F. Shamsa, S. N. Ostad, S. Emami, A. Shafiee, J. Davoodi, A. Foroumadi, Eur. J. Med. Chem. 2010, 45, 5384.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht1Krt77J&md5=57772e8e441ea876e717adea92eb8c26CAS |
[2] C. Bolchi, M. Pallavicini, C. Rusconi, L. Diomede, N. Ferri, A. Corsini, L. Fumagalli, A. Pedretti, G. Vistoli, E. Valoti, Bioorg. Med. Chem. Lett. 2007, 17, 6192.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtFOjt7zO&md5=1c488c301dd834767f909f58db7fb98bCAS |
[3] N. M. G. M. Appels, J. H. Beijnen, J. H. M. Schellensb, Oncologist 2005, 10, 565.
| Crossref | GoogleScholarGoogle Scholar |
[4] M. Vaidya, M. Weigt, M. Wiese, Eur. J. Med. Chem. 2009, 44, 4070.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXptlert78%3D&md5=6b0036deda2072994b68b218b7692805CAS |
[5] T. Equbal, O. Silakari, M. Ravikumar, Eur. J. Med. Chem. 2008, 43, 204.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXosFeksg%3D%3D&md5=3c310721688b8071051eb93aafe4a3fbCAS |
[6] P. Gilleron, N. Wlodarczyk, R. Houssin, A. Farce, G. Laconde, J. F. Goossens, A. Lemoine, N. Pommery, J. P. Henichart, R. Millet, Bioorg. Med. Chem. Lett. 2007, 17, 5465.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVGjurzJ&md5=54d67394253bac29ea4b866c6b8cb51bCAS |
[7] R. Tanaka, A. Rubio, N. K. Harn, D. Gernert, T. A. Grese, J. Eishima, M. Hara, N. Yoda, R. Ohashi, T. Kuwabara, S. Soga, S. Akinaga, S. Nara, Y. Kanda, Bioorg. Med. Chem. 2007, 15, 1363.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXisVWgtQ%3D%3D&md5=fd28aec98837038b3fe58c949153e485CAS |
[8] D. S. Puntambekar, R. Giridhar, M. R. Yadav, Eur. J. Med. Chem. 2008, 43, 142.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXosFelsA%3D%3D&md5=b7e06f796df6758124a5ec81301df3b3CAS |
[9] P. Angibaud, L. Mevellec, C. Meyer, X. Bourdrez, P. Lezouret, I. Pilatte, V. Poncelet, B. Roux, S. Merillon, D. W. End, J. Van Dun, W. Wouters, M. Venet, Eur. J. Med. Chem. 2007, 42, 702.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXlt1Gqt7s%3D&md5=89718a7d9a49d123f078bfafa799c941CAS |
[10] T. Equbal, O. Silakari, G. Rambabu, M. Ravikumar, Bioorg. Med. Chem. Lett. 2007, 17, 1594.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXit1yku70%3D&md5=ccd3e52d1a675390a7ac7e7820301e35CAS |
[11] P. Gilleron, R. Millet, R. Houssin, N. Wlodarczyk, A. Farce, A. Lemoine, J. F. Goossens, P. Chavatte, N. Pommery, J. P. Hénichart, Eur. J. Med. Chem. 2006, 41, 745.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XlvFygsLw%3D&md5=be66bacac5c90390ba4390fae9954944CAS |
[12] C. Y. Huang, T. M. Stauffer, C. L. Strickland, J. C. Reader, H. Huang, G. Li, A. B. Cooper, R. J. Doll, A. K. Ganguly, J. J. Baldwin, Bioorg. Med. Chem. Lett. 2006, 16, 507.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtlCiu7vN&md5=9e3113a618fef030d3275cd985092c12CAS |
[13] L. A. Hasvold, W. Wang, I. Gwaltney, L. Stephen, T. W. Rockway, L. T. J. Nelson, R. A. Mantei, S. A. Fakhoury, G. M. Sullivan, Q. Li, Bioorg. Med. Chem. Lett. 2003, 13, 4001.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXosVWrsLk%3D&md5=e456a548012e075cce1dd7ba7f9461c1CAS |
[14] C. Bolchi, M. Pallavicini, S. K. Bernini, G. Chiodini, A. Corsini, N. Ferri, L. Fumagalli, V. Straniero, E. Valoti, Bioorg. Med. Chem. Lett. 2011, 21, 5408.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtVKis7vI&md5=5497874967ee19dd127fbc165da38fe6CAS |
[15] A. M. E. Omar, A. M. Farghaly, A. A. B. Hazzai, N. H. Eshba, F. M. Sharabi, T. T. Daabees, J. Pharm. Sci. 1981, 70, 1075.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3MXmtVemsL8%3D&md5=48088474e7eda9f9c855a5351b60f5f8CAS |
[16] K. K. Maiti, O. Y. Jeon, W. S. Lee, S. K. Chung, Chem. – Eur. J. 2007, 13, 762.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVOntr8%3D&md5=6981889d19c85b9c90af546ebadd9f2fCAS |
[17] H. Z. Zhang, C. Crogan-Grundy, C. May, J. Drewe, B. Tseng, S. X. Cai, Bioorg. Med. Chem. 2009, 17, 2852.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjvV2hsrk%3D&md5=6c7afbf8f2c161236a5df6541dc96facCAS |
[18] E. J. Iwanowicz, S. H. Watterson, C. Liu, H. H. Gu, T. Mitt, K. Leftheris, J. C. Barrish, C. A. Fleener, K. Rouleau, N. Z. Sherbina, D. L. Hollenbaugh, Bioorg. Med. Chem. Lett. 2002, 12, 2931.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xntlaguro%3D&md5=9fc4beca469a79484af2da0239b0a99eCAS |
[19] F. D. Popp, H. Swarz, J. Org. Chem. 1961, 26, 4764.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF38XmtVeltg%3D%3D&md5=8b334b39cc2e4eb3bb1ba2e46510e66bCAS |
[20] P. E. Maligres, M. S. Waters, S. A. Weissman, J. C. McWilliams, S. Lewis, J. Cowen, R. A. Reamer, R. P. Volante, P. J. Reider, D. Askin, J. Heterocycl. Chem. 2003, 40, 229.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXjsVamt7k%3D&md5=a4103cfe354e6496f25b165be95637abCAS |
[21] D. Askin, S. Lewis, S. A. Weissman, U. S. Patent 6160118 2000.
[22] B. Simoneau, P. Lavallée, P. C. Anderson, M. Bailey, G. Bantle, S. Berthiaume, C. Chabot, G. Fazal, T. Halmos, W. W. Ogilvie, M.-A. Poupart, B. Thavonekham, Z. Xin, D. Thibeault, G. Bolger, M. Panzenbeck, R. Winquist, G. L. Jung, Bioorg. Med. Chem. 1999, 7, 489.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXitlGktbw%3D&md5=3d9cdd6486d72610ddc53e3f94e9b7e4CAS |
[23] G. Grethe, H. L. Lee, M. Uskokovic, A. Brossi, J. Org. Chem. 1968, 33, 491.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1cXmvVymsA%3D%3D&md5=29e28c400e556f573612cc77398dbd5dCAS |
[24] J. A. Grzyb, M. Shen, C. Yoshina-Ishii, W. Chi, R. S. Brown, R. A. Batey, Tetrahedron 2005, 61, 7153.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXlsVCisLk%3D&md5=3ed855b05f34f3050bc0eb3849d48327CAS |
[25] D. M. Shendage, R. Fröhlich, G. Haufe, Org. Lett. 2004, 6, 3675.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXnvVKqtr4%3D&md5=bf0104c5eb1fb426fe0587fd05096b16CAS |
[26] Y. Zhang, W. Williams, C. Torrence-Campbell, W. D. Bowen, K. C. Rice, J. Med. Chem. 1998, 41, 4950.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXnt1Cltb4%3D&md5=3081e0923c2a74ff5a1afcb14511ba0cCAS |
[27] R. Pingaew, P. Tongraung, A. Worachartcheewan, C. Nantasenamat, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, Med. Chem. Res. 2012,
| Crossref | GoogleScholarGoogle Scholar |
[28] Q. Li, T. Li, K. W. Woods, W. Z. Gu, J. Cohen, V. S. Stoll, T. Galicia, C. Hutchins, D. Frost, S. H. Rosenberg, Bioorg. Med. Chem. Lett. 2005, 15, 2918.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXks1Witrc%3D&md5=a04b9c5c4e0df97bdb8806f9ff50a513CAS |
[29] D. N. Nguyen, C. A. Stump, E. S. Walsh, C. Fernandes, J. P. Davide, M. Ellis-Hutchings, R. G. Robinson, T. M. Williams, R. B. Lobell, H. E. Huber, Bioorg. Med. Chem. Lett. 2002, 12, 1269.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XivVOrs7g%3D&md5=9acbe4743b2a163371dc3a1bf258d575CAS |
[30] P. Angibaud, A. K. Saha, X. Bourdrez, D. W. End, E. Freyne, P. Lezouret, G. Mannens, L. Mevellec, C. Meyer, I. Pilatte, V. Poncelet, B. Roux, G. Smets, J. Van Dun, M. Venet, W. Wouters, Bioorg. Med. Chem. Lett. 2003, 13, 4361.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXpt1yrtb8%3D&md5=3271843431caac8d87306932332bb1daCAS |
[31] P. Angibaud, X. Bourdrez, A. Devine, D. W. End, E. Freyne, Y. Ligny, P. Muller, G. Mannens, I. Pilatte, V. Poncelet, S. Skrzat, G. Smets, J. Van Dun, P. Van Remoortere, M. Venet, W. Wouters, Bioorg. Med. Chem. Lett. 2003, 13, 1543.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXivFelsrg%3D&md5=a1668319bc278e29251bbe115e97b476CAS |
[32] http://www.who.int/mediacentre/factsheets/fs297/en/
[33] http://globocan.iarc.fr/factsheets/populations/factsheet.asp?uno=900
[34] M. Brink, A. F. P. M. de Goeij, M. P. Weijenberg, G. M. J. M. Roemen, M. H. F. M. Lentjes, M. M. M. Pachen, K. M. Smits, A. P. de Bruïne, R. A. Goldbohm, P. A. van den Brandt, Carcinogenesis 2003, 24, 703.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXjslWht78%3D&md5=3e479d12910d0a34f0a741cf89bcf82bCAS |
[35] K. Okudela, H. Hayashi, T. Ito, T. Yazawa, T. Suzuki, Y. Nakane, H. Sato, H. Ishi, K. Xin, A. Masuda, Am. J. Pathol. 2004, 164, 91.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXlsVCgsg%3D%3D&md5=6baacbbcea7b7dd620d9dc43ec849443CAS |
[36] B. B. Kedzia, P. X. Armendarez, K. Nakamoto, J. Inorg. Nucl. Chem. 1968, 30, 849.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1cXkt1ehtLc%3D&md5=784633720b8d76af660be57187de5f31CAS |
[37] T. Barman, G. N. Mukherjee, J. Chem. Sci. 2008, 120, 377.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtVaktbbJ&md5=4b6b736476eb3d1acbf7aa6df0f1627cCAS |
[38] N. Raman, S. Esthar, C. Thangaraja, J. Chem. Sci. 2004, 116, 209.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXmvVOitrg%3D&md5=a081d100cc7d0067887306e73a7c6000CAS |
