Copyright (c) 2018 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Biological Activity of Some Chalcone Derivatives of Cholic Acid
Corresponding Author(s) : Abbas S. Abd
Asian Journal of Chemistry,
Vol. 30 No. 11 (2018): Vol 30 Issue 11
Abstract
N-(4-acetylphenyl)-3¢,7¢,12¢-trihydroxy-5¢-cholan-24-amide was synthesized from reaction of cholic acid with 4-amino acetophenone then the obtained product reacts with some substituted benzaldehyde derivatives to prepare chalcone derivatives. Finally, the products were allowed to react with thiourea to give thiazine derivatives. The reactions were monitored by thin-layer chromatography (TLC) technique. All the new compounds were characterized by melting points, elemental analysis, FT-IR, 1H NMR, 13C NMR spectroscopies. Antimicrobial activity of the synthesized derivatives was also determined.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- D.W. Russell, Annu. Rev. Biochem., 72, 137 (2003); https://doi.org/10.1146/annurev.biochem.72.121801.161712.
- B. Hazra, V. Pore, S. Dey, S. Datta, M. Darokar, D. Saikia, S.P.S. Khanuja and A.P. Thakur, Bioorg. Med. Chem. Lett., 14, 773 (2004); https://doi.org/10.1016/j.bmcl.2003.11.018.
- D. Kakati, R.K. Sarma, R. Saikia, N.C. Barua and J.C. Sarma, Steroids, 78, 321 (2013); https://doi.org/10.1016/j.steroids.2012.12.003.
- L.R. Fernández, L. Svetaz, E. Butassi, S.A. Zacchino, J.A. Palermo and M. Sánchez, Steroids, 108, 68 (2016) https://doi.org/10.1016/j.steroids.2016.01.014.
- D.B. Salunke, B.G. Hazra, V.S. Pore, M.K. Bhat, P.B. Nahar and M.V. Deshpande, J. Med. Chem., 47, 1591 (2004); https://doi.org/10.1021/jm030376y.
- G. Visbal, G. San-Blas, A. Maldonado, A. Alvarez-Aular, M.V. Capparelli and J. Murgich, Steroids, 76, 1069 (2011); https://doi.org/10.1016/j.steroids.2011.04.012.
- A. Scozzafava and C.T. Supuran, Bioorg. Med. Chem. Lett., 12, 1551 (2002); https://doi.org/10.1016/S0960-894X(02)00252-4.
- M. Bülbül, N. Saracoglu, Ö. Irfan Küfrevioglu and M. Ciftci, Bioorg. Med. Chem., 10, 2561 (2002); https://doi.org/10.1016/S0968-0896(02)00104-9.
- J.A. Santos, H.C. Polonini, É.Y. Suzuki, N.R.B. Raposo and A.D. da Silva, Steroids, 8, 114 (2015); https://doi.org/10.1016/j.steroids.2015.03.009.
- C. Li, A.S. Peters, E.L. Meredith, G.W. Allman and P.B. Savage, J. Am. Chem. Soc., 120, 2961 (1998); https://doi.org/10.1021/ja973881r.
- R. Boyce, G. Li, H.P. Nestler, T. Suenaga and W.C. Still, J. Am. Chem. Soc., 116, 7955 (1994); https://doi.org/10.1021/ja00096a086.
- A.P. Davis, J.J. Perry and R.P. Williams, J. Am. Chem. Soc., 119, 1793 (1997); https://doi.org/10.1021/ja9629930.
- J. Mckenna, J.M. McKenna and D.W. Thornthwaite, J. Chem. Soc. Chem. Commun., 809 (1977); https://doi.org/10.1039/c39770000809.
- V. Janout, M. Lanier and S.L. Regen, J. Am. Chem. Soc., 118, 1573 (1996); https://doi.org/10.1021/ja953261v.
- W. Kramer and G. Wess, Eur. J. Clin. Invest., 26, 715 (1996); https://doi.org/10.1111/j.1365-2362.1996.tb02383.x.
- T. Lehmann and J. Engels, Bioorg. Med. Chem., 9, 1827 (2001); https://doi.org/10.1016/S0968-0896(01)00079-7.
- H.S. Kim, B.S. Choi, K.C. Kwon, S.O. Lee, H.J. Kwak and C.H. Lee, Bioorg. Med. Chem., 8, 2059 (2000); https://doi.org/10.1016/S0968-0896(00)00128-0.
- H.M. Willemen, L.C.P.M. de Smet, A. Koudijs, M.C.A. Stuart, I.G.A.M. Heikamp-de Jong, A.T.M. Marcelis and E.J.R. Sudhölter, Angew. Chem. Int. Ed., 41, 4275 (2002); https://doi.org/10.1002/1521-3773(20021115)41:22<4275::AID-ANIE4275>3.0.CO;2-U.
- A.A. Williams, E.W. Sugandhi, R.V. Macri, J.O. Falkinham III and R.D. Gandour, J. Antimicrob. Chemother., 59, 451 (2007); https://doi.org/10.1093/jac/dkl503.
- E.W. Sugandhi, J.O. Falkinham III and R.D. Gandour, Bioorg. Med. Chem., 15, 3842 (2007); https://doi.org/10.1016/j.bmc.2007.03.017.
- M. Vallejo, M.A. Castro, M. Medarde, R.I.R. Macias, M.R. Romero, M.Y. El-Mir, M.J. Monte, O. Briz, M.A. Serrano and J.J.G. Marin, Biochem. Pharmacol., 73, 1394 (2007); https://doi.org/10.1016/j.bcp.2006.12.027.
- R. Paschke, J. Kalbitz, C. Paetz, M. Luckner, T. Mueller, H.J. Schmoll, H. Mueller, E. Sorkau and E. Sinn, J. Inorg. Biochem., 94, 335 (2003); https://doi.org/10.1016/S0162-0134(03)00024-2.
References
D.W. Russell, Annu. Rev. Biochem., 72, 137 (2003); https://doi.org/10.1146/annurev.biochem.72.121801.161712.
B. Hazra, V. Pore, S. Dey, S. Datta, M. Darokar, D. Saikia, S.P.S. Khanuja and A.P. Thakur, Bioorg. Med. Chem. Lett., 14, 773 (2004); https://doi.org/10.1016/j.bmcl.2003.11.018.
D. Kakati, R.K. Sarma, R. Saikia, N.C. Barua and J.C. Sarma, Steroids, 78, 321 (2013); https://doi.org/10.1016/j.steroids.2012.12.003.
L.R. Fernández, L. Svetaz, E. Butassi, S.A. Zacchino, J.A. Palermo and M. Sánchez, Steroids, 108, 68 (2016) https://doi.org/10.1016/j.steroids.2016.01.014.
D.B. Salunke, B.G. Hazra, V.S. Pore, M.K. Bhat, P.B. Nahar and M.V. Deshpande, J. Med. Chem., 47, 1591 (2004); https://doi.org/10.1021/jm030376y.
G. Visbal, G. San-Blas, A. Maldonado, A. Alvarez-Aular, M.V. Capparelli and J. Murgich, Steroids, 76, 1069 (2011); https://doi.org/10.1016/j.steroids.2011.04.012.
A. Scozzafava and C.T. Supuran, Bioorg. Med. Chem. Lett., 12, 1551 (2002); https://doi.org/10.1016/S0960-894X(02)00252-4.
M. Bülbül, N. Saracoglu, Ö. Irfan Küfrevioglu and M. Ciftci, Bioorg. Med. Chem., 10, 2561 (2002); https://doi.org/10.1016/S0968-0896(02)00104-9.
J.A. Santos, H.C. Polonini, É.Y. Suzuki, N.R.B. Raposo and A.D. da Silva, Steroids, 8, 114 (2015); https://doi.org/10.1016/j.steroids.2015.03.009.
C. Li, A.S. Peters, E.L. Meredith, G.W. Allman and P.B. Savage, J. Am. Chem. Soc., 120, 2961 (1998); https://doi.org/10.1021/ja973881r.
R. Boyce, G. Li, H.P. Nestler, T. Suenaga and W.C. Still, J. Am. Chem. Soc., 116, 7955 (1994); https://doi.org/10.1021/ja00096a086.
A.P. Davis, J.J. Perry and R.P. Williams, J. Am. Chem. Soc., 119, 1793 (1997); https://doi.org/10.1021/ja9629930.
J. Mckenna, J.M. McKenna and D.W. Thornthwaite, J. Chem. Soc. Chem. Commun., 809 (1977); https://doi.org/10.1039/c39770000809.
V. Janout, M. Lanier and S.L. Regen, J. Am. Chem. Soc., 118, 1573 (1996); https://doi.org/10.1021/ja953261v.
W. Kramer and G. Wess, Eur. J. Clin. Invest., 26, 715 (1996); https://doi.org/10.1111/j.1365-2362.1996.tb02383.x.
T. Lehmann and J. Engels, Bioorg. Med. Chem., 9, 1827 (2001); https://doi.org/10.1016/S0968-0896(01)00079-7.
H.S. Kim, B.S. Choi, K.C. Kwon, S.O. Lee, H.J. Kwak and C.H. Lee, Bioorg. Med. Chem., 8, 2059 (2000); https://doi.org/10.1016/S0968-0896(00)00128-0.
H.M. Willemen, L.C.P.M. de Smet, A. Koudijs, M.C.A. Stuart, I.G.A.M. Heikamp-de Jong, A.T.M. Marcelis and E.J.R. Sudhölter, Angew. Chem. Int. Ed., 41, 4275 (2002); https://doi.org/10.1002/1521-3773(20021115)41:22<4275::AID-ANIE4275>3.0.CO;2-U.
A.A. Williams, E.W. Sugandhi, R.V. Macri, J.O. Falkinham III and R.D. Gandour, J. Antimicrob. Chemother., 59, 451 (2007); https://doi.org/10.1093/jac/dkl503.
E.W. Sugandhi, J.O. Falkinham III and R.D. Gandour, Bioorg. Med. Chem., 15, 3842 (2007); https://doi.org/10.1016/j.bmc.2007.03.017.
M. Vallejo, M.A. Castro, M. Medarde, R.I.R. Macias, M.R. Romero, M.Y. El-Mir, M.J. Monte, O. Briz, M.A. Serrano and J.J.G. Marin, Biochem. Pharmacol., 73, 1394 (2007); https://doi.org/10.1016/j.bcp.2006.12.027.
R. Paschke, J. Kalbitz, C. Paetz, M. Luckner, T. Mueller, H.J. Schmoll, H. Mueller, E. Sorkau and E. Sinn, J. Inorg. Biochem., 94, 335 (2003); https://doi.org/10.1016/S0162-0134(03)00024-2.