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Design and Synthesis of 3-Substituted Indolin-2-one Derivatives with Methyl (E)-2-(3-Methoxy)acrylate Moiety
Corresponding Author(s) : Yu-Liang Wang
Asian Journal of Chemistry,
Vol. 27 No. 8 (2015): Vol 27 Issue 8
Abstract
In this article, fifteen indolin-2-one derivatives with methyl (E)-2-(3-methoxy)acrylate group were designed and synthesized. The structures of target compounds were confirmed by 1H NMR, IR and HR-MS spectra analysis.
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- B. Ma, C.F. Wu, J.Y. Yang, R. Wang, Y. Kano and D. Yuan, Helv. Chim. Acta, 92, 1575 (2009); doi:10.1002/hlca.200900021.
- R. Sakhuja, S.S. Panda, L. Khanna, S. Khurana and S.C. Jain, Bioorg. Med. Chem. Lett., 21, 5465 (2011); doi:10.1016/j.bmcl.2011.06.121.
- S. Edmondson, S.J. Danishefsky, L. Sepp-Lorenzino and N. Rosen, J. Am. Chem. Soc., 121, 2147 (1999); doi:10.1021/ja983788i.
- S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, IL Farmaco, 54, 624 (1999); doi:10.1016/S0014-827X(99)00075-0.
- N. Karalı, A. Gürsoy, F. Kandemirli, N. Shvets, F.B. Kaynak, S. Özbey, V. Kovalishyn and A. Dimoglo, Bioorg. Med. Chem., 15, 5888 (2007); doi:10.1016/j.bmc.2007.05.063.
- A.A. Raj, R. Raghunathan, M.R. Sridevi Kumari and N. Raman, Bioorg. Med. Chem., 11, 407 (2003); doi:10.1016/S0968-0896(02)00439-X.
- S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Pharm. Acta Helv., 74, 11 (1999); doi:10.1016/S0031-6865(99)00010-2.
- D.C. Quenelle, K.A. Keith and E.R. Kern, Antiviral Res., 71, 24 (2006); doi:10.1016/j.antiviral.2006.02.010.
- K. Singh, M. Verma, S.N. Pandey and J.P. Stable, Acta Pharm., 54, 49 (2004).
- S.K. Sridhar and A. Ramesh, Biol. Pharm. Bull., 24, 1149 (2001); doi:10.1248/bpb.24.1149.
- A.T. Fadl and F.A.S. Bin-Jubair, Int. J. Res. Pharm. Sci., 1, 113 (2010).
- M.A. Hussein, T.A. Fadl and A. Hussein, Pharm. Sci., 28, 131 (2005).
- N. Karalı, A. Gürsoy, F. Kandemirli, N. Shvets, F.B. Kaynak, S. Özbey, V. Kovalishyn and A. Dimoglo, Med. Chem., 15, 5888 (2007); doi:10.1016/j.bmc.2007.05.063.
- A. Gursoy and N. Karal, Eur. J. Med. Chem., 38, 633 (2003); doi:10.1016/S0223-5234(03)00085-0.
- T. Annie, T. Fong, L.K. Shawver and L. Sun, Cancer Res., 59, 99 (1999).
- P. Marzola, A. Degrassi and L. Calderan, Clin. Cancer Res., 10, 739 (2004); doi:10.1158/1078-0432.CCR-0828-03.
- C.R. Prakash, P. Theivendren and S. Raja, Pharmacol. Pharm., 3, 62 (2012); doi:10.4236/pp.2012.31010.
- D.M. McLean, Ann. N. Y. Acad. Sci., 284(1 Third Confere), 118 (1977); doi:10.1111/j.1749-6632.1977.tb21942.x.
- S.B. Bari, A.O. Agrawal and U.K. Patil, J. Sci. Islam. Rep. Iran, 19, 217 (2008).
- R. Gudipati, R.N.R. Anreddy and S. Manda, Saudi Pharm. J., 19, 153 (2011); doi:10.1016/j.jsps.2011.03.002.
- P.L. Zhao, F. Wang, M.Z. Zhang, Z.-M. Liu, W. Huang and G.-F. Yang, J. Agric. Food Chem., 56, 10767 (2008); doi:10.1021/jf802343p.
- B. Srinivas, Der Pharma Chemica, 2, 378 (2010).
- G. Chen, Y. Wang, X. Hao, S. Mu and Q. Sun, Chem. Cent. J., 5, 37 (2011); doi:10.1186/1752-153X-5-37.
References
B. Ma, C.F. Wu, J.Y. Yang, R. Wang, Y. Kano and D. Yuan, Helv. Chim. Acta, 92, 1575 (2009); doi:10.1002/hlca.200900021.
R. Sakhuja, S.S. Panda, L. Khanna, S. Khurana and S.C. Jain, Bioorg. Med. Chem. Lett., 21, 5465 (2011); doi:10.1016/j.bmcl.2011.06.121.
S. Edmondson, S.J. Danishefsky, L. Sepp-Lorenzino and N. Rosen, J. Am. Chem. Soc., 121, 2147 (1999); doi:10.1021/ja983788i.
S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, IL Farmaco, 54, 624 (1999); doi:10.1016/S0014-827X(99)00075-0.
N. Karalı, A. Gürsoy, F. Kandemirli, N. Shvets, F.B. Kaynak, S. Özbey, V. Kovalishyn and A. Dimoglo, Bioorg. Med. Chem., 15, 5888 (2007); doi:10.1016/j.bmc.2007.05.063.
A.A. Raj, R. Raghunathan, M.R. Sridevi Kumari and N. Raman, Bioorg. Med. Chem., 11, 407 (2003); doi:10.1016/S0968-0896(02)00439-X.
S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Pharm. Acta Helv., 74, 11 (1999); doi:10.1016/S0031-6865(99)00010-2.
D.C. Quenelle, K.A. Keith and E.R. Kern, Antiviral Res., 71, 24 (2006); doi:10.1016/j.antiviral.2006.02.010.
K. Singh, M. Verma, S.N. Pandey and J.P. Stable, Acta Pharm., 54, 49 (2004).
S.K. Sridhar and A. Ramesh, Biol. Pharm. Bull., 24, 1149 (2001); doi:10.1248/bpb.24.1149.
A.T. Fadl and F.A.S. Bin-Jubair, Int. J. Res. Pharm. Sci., 1, 113 (2010).
M.A. Hussein, T.A. Fadl and A. Hussein, Pharm. Sci., 28, 131 (2005).
N. Karalı, A. Gürsoy, F. Kandemirli, N. Shvets, F.B. Kaynak, S. Özbey, V. Kovalishyn and A. Dimoglo, Med. Chem., 15, 5888 (2007); doi:10.1016/j.bmc.2007.05.063.
A. Gursoy and N. Karal, Eur. J. Med. Chem., 38, 633 (2003); doi:10.1016/S0223-5234(03)00085-0.
T. Annie, T. Fong, L.K. Shawver and L. Sun, Cancer Res., 59, 99 (1999).
P. Marzola, A. Degrassi and L. Calderan, Clin. Cancer Res., 10, 739 (2004); doi:10.1158/1078-0432.CCR-0828-03.
C.R. Prakash, P. Theivendren and S. Raja, Pharmacol. Pharm., 3, 62 (2012); doi:10.4236/pp.2012.31010.
D.M. McLean, Ann. N. Y. Acad. Sci., 284(1 Third Confere), 118 (1977); doi:10.1111/j.1749-6632.1977.tb21942.x.
S.B. Bari, A.O. Agrawal and U.K. Patil, J. Sci. Islam. Rep. Iran, 19, 217 (2008).
R. Gudipati, R.N.R. Anreddy and S. Manda, Saudi Pharm. J., 19, 153 (2011); doi:10.1016/j.jsps.2011.03.002.
P.L. Zhao, F. Wang, M.Z. Zhang, Z.-M. Liu, W. Huang and G.-F. Yang, J. Agric. Food Chem., 56, 10767 (2008); doi:10.1021/jf802343p.
B. Srinivas, Der Pharma Chemica, 2, 378 (2010).
G. Chen, Y. Wang, X. Hao, S. Mu and Q. Sun, Chem. Cent. J., 5, 37 (2011); doi:10.1186/1752-153X-5-37.