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Vol. 26 No. 11 (2014): Vol 26 Issue 11

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Concise Syntheses and Antitumor Activities of a-Hydroxy(mercapto)amide Derivatives

https://doi.org/10.14233/ajchem.2014.15894
Y.X. Li
Chemistry and Chemical Engineering Department, Huaihua University, 612 Yingfeng Road, Huaihua 418008, P.R. China
Z. Qiu
Chemistry and Chemical Engineering Department, Huaihua University, 612 Yingfeng Road, Huaihua 418008, P.R. China

Corresponding Author(s) : Y.X. Li

hhxyyxli@163.com

Asian Journal of Chemistry, Vol. 26 No. 11 (2014): Vol 26 Issue 11

Abstract

A novel process for preparing a-hydroxy(mercapto)-N-[6-(3-phenylureido)hexyl]amide derivatives was described and three new compounds 8-10 were synthesized. The antitumor activities on Hut102, MCF7 and HepG2 of the compounds 7-10 were assayed. The results showed that the target compounds 7-10 exhibited some antitumor activities against tumor cell lines.

Keywords

Histone deacetylase inhibitors Drug design Antitumor activity α-Hydroxy(mercapto)amide
Li, Y., & Qiu, Z. (2014). Concise Syntheses and Antitumor Activities of a-Hydroxy(mercapto)amide Derivatives. Asian Journal of Chemistry, 26(11), 3219–3223. https://doi.org/10.14233/ajchem.2014.15894
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References
  1. P.A. Marks, R.A. Rifkind, V.M. Richon, R. Breslow, T. Miller and W.K. Kelly, Nat. Rev. Cancer, 1, 194 (2001); doi:10.1038/35106079.
  2. A. Vaisburg, I. Paquin, N. Bernstein, S. Frechette, F. Gaudette, S. Leit, O. Moradei, S. Raeppel, N. Zhou, G. Bouchain, S.H. Woo, Z. Jin, J. Gillespie, J. Wang, M. Fournel, P.T. Yan, M.-C. Trachy-Bourget, M.-F. Robert, A. Lu, J. Yuk, J. Rahil, A.R. MacLeod, J.M. Besterman, Z. Li and D. Delorme, Bioorg. Med. Chem. Lett., 17, 6729 (2007); doi:10.1016/j.bmcl.2007.10.050.
  3. D.C. Drummond, G.K. Noble, D.B. Kirpotin, Z. Guo, G.K. Scott and C.C. Benz, Annu. Rev. Pharmacol. Toxicol., 45, 495 (2005); doi:10.1146/annurev.pharmtox.45.120403.095825.
  4. M.F. Fraga, E. Ballestar, A. Villar-Garea, M. Boix-Chornet, J. Espada, G. Schotta, T. Bonaldi, C. Haydon, S. Ropero, K. Petrie, N.G. Iyer, A. Pérez-Rosado, E. Calvo, J.A. Lopez, A. Cano, M.J. Calasanz, D. Colomer, M.Á. Piris, N. Ahn, A. Imhof, C. Caldas, T. Jenuwein and M. Esteller, Nat. Genet., 37, 391 (2005); doi:10.1038/ng1531.
  5. C.M. Marson, T. Mahadevan, J. Dines, S. Sengmany, J.M. Morrell, J.P. Alao, S.P. Joel, D.M. Vigushin and R.C. Coombes, Bioorg. Med. Chem. Lett., 17, 136 (2007); doi:10.1016/j.bmcl.2006.09.085.
  6. J.E. Bolden, M.J. Peart and R.W. Johnstone, Nat. Rev. Drug Discov., 5, 769 (2006); doi:10.1038/nrd2133.
  7. T. Hideshima, J.E. Bradner, J. Wong, D. Chauhan, P. Richardson, S.L. Schreiber and K.C. Anderson, Proc. Natl. Acad. Sci. USA, 102, 8567 (2005); doi:10.1073/pnas.0503221102.
  8. M. Yoshida, S. Horinouchi and T. Beppu, Bioessays, 17, 423 (1995); doi:10.1002/bies.950170510.
  9. H. Rajak, A. Agarawal, P. Parmar, B.S. Thakur, R. Veerasamy, P.C. Sharma and M.D. Kharya, Bioorg. Med. Chem. Lett., 21, 5735 (2011); doi:10.1016/j.bmcl.2011.08.022.
  10. T.A. Miller, D.J. Witter and S. Belvedere, J. Med. Chem., 46, 5097 (2003); doi:10.1021/jm0303094.
  11. P.C. Chen, V. Patil, W. Guerrant, P. Green and A.K. Oyelere, Bioorg. Med. Chem., 16, 4839 (2008); doi:10.1016/j.bmc.2008.03.050.
  12. A.P. Kozikowski, Y.F. Chen, A. Gaysin, B. Chen, M.A. D’Annibale, C.M. Suto and B.C. Langley, J. Med. Chem., 50, 3054 (2007); doi:10.1021/jm070178x.
  13. T. SuzukiS. HisakawaY. Itoh. T. Suzuki, S. Hisakawa, Y. Itoh, N. Suzuki, K. Takahashi, M. Kawahata, K. Yamaguchi, H. Nakagawa and N. Miyata, Bioorg. Med. Chem. Lett., 17, 4208 (2007); doi:10.1016/j.bmcl.2007.05.040.
  14. K. Dodo, T. Minato and Y. Hashimoto, Chem. Pharm. Bull. (Tokyo), 57, 190 (2009); doi:10.1248/cpb.57.190.
  15. J.J. Diaz-Mochon, M.A. Fara, R.M. Sanchez-Martin and M. Bradley, Tetrahedron Lett., 49, 923 (2008); doi:10.1016/j.tetlet.2007.11.122.
  16. W. Zhang, C.H.T. Chen and T. Nagashima, Tetrahedron Lett., 44, 2065 (2003); doi:10.1016/S0040-4039(03)00178-3.
  17. J. Scheerder, J.F.J. Engbersen, A. Casnati, R. Ungaro and D.N. Reinhoudt, J. Org. Chem., 60, 6448 (1995); doi:10.1021/jo00125a035.
  18. M.A. Cinelli, B. Cordero, T.S. Dexheimer, Y. Pommier and M. Cushman, Bioorg. Med. Chem., 17, 7145 (2009); doi:10.1016/j.bmc.2009.08.066.
  19. M. Somei, Y. Fukui, M. Hasegawa, N. Oshikiri and T. Hayashi, Heterocycles, 53, 1725 (2000); doi:10.3987/COM-00-8930.
  20. S. Paramasivam, A. Balakrishnan, O. Dmitrenko, A. Godert, T.P. Begley, F. Jordan and T. Polenova, J. Phys. Chem. B, 115, 730 (2011); doi:10.1021/jp109765b.
  21. S.P. Breazzano and D.L. Boger, J. Am. Chem. Soc., 133, 18495 (2011); doi:10.1021/ja208570q.
  22. B. Chen, P.A. Petukhov, M. Jung, A. Velena, E. Eliseeva, A. Dritschilo and A.P. Kozikowski, Bioorg. Med. Chem. Lett., 15, 1389 (2005); doi:10.1016/j.bmcl.2005.01.006.
  23. K.J.C. van Bommel, M.R. de Jong, G.A. Metselaar, W. Verboom, J. Huskens, R. Hulst, H. Kooijman, A.L. Spek and D.N. Reinhoudt, Chem. Eur. J., 7, 3603 (2001); doi:10.1002/1521-3765(20010817)7:16<3603::AID-CHEM3603>3.0.CO;2-E.
  24. A.M.A. Muhanna, E. Ortiz-Salmerón, L. Garcia-Fuentes, J.J. Giménez-Martínez and A. Vargas-Berenguel, Tetrahedron Lett., 44, 6125 (2003); doi:10.1016/S0040-4039(03)01432-1.
  25. Y.C. Luo, H. Zhang and Y. Yang, Jingxi Huagong Zhongjianti, 37, 43 (2007).
  26. R.A. Aitken, D.P. Armstrong, R.H.B. Galt and S.T.E. Mesher, J. Chem. Soc., Perkin Trans. 1, 935 (1997); doi:10.1039/a605539g.
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