Copyright (c) 2015 AJC
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Synthesis of Piperazine Derivatives and Biological Evaluation of Its Inhibitory Activities on Vascular Smooth Muscle Cell Proliferation
Corresponding Author(s) : Jian Xin Chen
Asian Journal of Chemistry,
Vol. 27 No. 4 (2015): Vol 27 Issue 4
Abstract
A series of new N-substituted benzyl piperazine derivatives were synthesized using the appropriate synthetic route. The new compounds were characterized by IR, 1H NMR, MS and elemental analysis. All the compounds were screened for their inhibitory activities on vascular smooth muscle cell proliferation. Some of the compounds demonstrated moderate to good inhibition of vascular smooth muscle cell proliferation. The compounds (2h, 6h) were approximately equivalent in activity to heparin as a potent inhibitor. The possible structure-activity relationship of the inhibitory activity of all compounds was also discussed.
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References
A.V. Finn, M. Nakano, J. Narula, F.D. Kolodgie and R. Virmani, Arterioscler. Thromb. Vasc. Biol., 30, 1282 (2010); doi:10.1161/ATVBAHA.108.179739.
A. Mahmud and J. Feely, Am. J. Hypertens., 15, 321 (2002); doi:10.1016/S0895-7061(01)02313-5.
M.V. Autieri, C.J. Carbone and H. Eisen, J. Heart Lung Transplant., 20, 198 (2001); doi:10.1016/S1053-2498(00)00418-6.
T. Jacob, E. Ascher, D. Alapat, Y. Olevskaia and A. Hingorani, Eur. J. Vasc. Endovasc. Surg., 29, 470 (2005); doi:10.1016/j.ejvs.2005.01.030.
A. Sanmartin, R. Foncea, F. Laurindo, R. Ebensperger, K. Griendling and F. Leighton, Free Radic. Biol. Med., 42, 1671 (2007); doi:10.1016/j.freeradbiomed.2007.02.002.
N. Fujita, Y. Furukawa, J. Du, N. Itabashi, G. Fujisawa, K. Okada, T. Saito and S. Ishibashi, Mol. Cell. Endocrinol., 192, 75 (2002); doi:10.1016/S0303-7207(02)00108-9.
M. Kimura, T. Masuda, K. Yamada, M. Mitani, N. Kubota, N. Kawakatsu, K. Kishii, M. Inazu, Y. Kiuchi, K. Oguchi and T. Namiki, Bioorg. Med. Chem., 12, 3069 (2004); doi:10.1016/j.bmc.2004.02.041.
A. Alves-Rodrigues, R. Leurs, E. Willems and H. Timmerman, Arch. Pharm., 329, 413 (1996); doi:10.1002/ardp.19963290808.
M.P. Chandler, W.C. Stanley, H. Morita, G. Suzuki, O. Nass, B. Blackburn, A. Wolfe and H. Sabbah, J. Mol. Cell. Cardiol., 34, 81 (2002); doi:10.1016/S0022-2828(02)91016-3.
Y. Rival, R. Hoffmann, B. Didier, V. Rybaltchenko, J.-J. Bourguignon and C.G. Wermuth, J. Med. Chem., 41, 311 (1998); doi:10.1021/jm9705418.
A.H. Ford, Org. Synth., 30, 84 (1963).
S. Rajagopalan and J.R. Johnson, Org. Synth., 3, 425 (1955).
S. Gunther, R.W. Alexander, W.J. Atkinson and M.A. Gimbrone, J. Cell Biol., 92, 289 (1982); doi:10.1083/jcb.92.2.289.