Copyright (c) 2017 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Antiproliferative Activity of Certain Meclofenamic Acid Amides
Corresponding Author(s) : Tilal Elsaman
Asian Journal of Chemistry,
Vol. 29 No. 2 (2017): Vol 29 Issue 2
Abstract
Synthesis of new meclofenamic acid amide derivatives is reported using various amino acid esters and dicyclohexylcarbodiimide as coupling agent. All of the synthesized compounds were characterized by their FT-IR, 1H NMR, 13C NMR and mass spectral data. The antiproliferative activity against human adenocarcinoma cell line HT29 was determined. Compounds 3, 4, 6, 7, 9, 10 and 11 displayed excellent inhibitory activity compared to the parent drug. Of these seven initial hits, compound 7 was the most active.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- I. Hilmi and K. Goh, Chin. J. Dig. Dis., 7, 1 (2006).
- J.J. Johnson and H. Mukhtar, Cancer Lett., 255, 170 (2007).
- R. Ettarh, A. Cullen and A. Calamai, Pharmaceuticals, 3, 2007 (2010).
- E.J. Greenspan, J.P. Madigan, L.A. Boardman and D.W. Rosenberg, Cancer Prev. Res., 4, 161 (2011).
- H.N. Tinsley, B.D. Gary, J. Thaiparambil, N. Li, W. Lu, Y. Li, Y.Y. Maxuitenko, A.B. Keeton and G.A. Piazza, Cancer Prev. Res., 3, 1303 (2010).
- M. Baumann and I.R. Baxendale, Beilstein J. Org. Chem., 9, 2265 (2013).
- G.A. Piazza, A.B. Keeton, H.N. Tinsley, B.D. Gary, J.D. Whitt, B. Mathew, J. Thaiparambil, L. Coward, G. Gorman, Y. Li, B. Sani, J.V. Hobrath, Y.Y. Maxuitenko and R.C. Reynolds, Cancer Prev. Res., 2, 572 (2009).
- M. Marjanovic, B. Zorc, L. Pejnovic, M. Zovko and M. Kralj, Chem. Biol. Drug Des., 69, 222 (2007).
- T. Elsaman, O.A.A. Aldeeb, T. Aboul-Fadl and A. Al-Dhfyan, Der Pharma Chem., 8, 434 (2016).
- R.K. Yeh, J. Chen, J.L. Williams, M. Baluch, T.R. Hundley, R.E. Rosenbaum, S. Kalala, F. Traganos, F. Benardini, P. Del Soldato, K. Kashfi and B. Rigas, Biochem. Pharmacol., 67, 2197 (2004).
- T. Aboul-Fadl, S.S. Al-Hamad, K. Lee, N. Li, B.D. Gary, A.B. Keeton, G.A. Piazza and M.K. Abdel-Hamid, Med. Chem. Res., 23, 4177 (2014).
- I. Delgado-Enciso, A.D. Soriano-Hernández, A. Rodriguez-Hernandez, H.R. Galvan-Salazar, D.A. Montes-Galindo, R. Martinez-Martinez, L.L. Valdez-Velazquez, R. Gonzalez-Alvarez, F. Espinoza-Gómez, O.A. Newton-Sanchez, A. Lara-Esqueda and J. Guzman-Esquivel, Int. Braz. J. Urol., 41, 1002 (2015).
- T. Aboul-Fadl, T. Elsaman, O.A. Al-Deeb, H.A. Ghabbour, C.S. Chidan Kumar and H.-K. Fun, Asian J. Chem., 26, 5249 (2014).
- A. Leo, Chem. Rev., 93, 1281 (1993).
- M. Kralj, S. Kapitanovic, D. Kovacevic, J. Lukac, S. Spaventi and K. Pavelic, J. Cancer Res. Clin. Oncol., 127, 173 (2001).
- P. Siraki, A. Chevaldina and T. O’Brien, Chem. Biol. Interact., 151, 177 (2005).
References
I. Hilmi and K. Goh, Chin. J. Dig. Dis., 7, 1 (2006).
J.J. Johnson and H. Mukhtar, Cancer Lett., 255, 170 (2007).
R. Ettarh, A. Cullen and A. Calamai, Pharmaceuticals, 3, 2007 (2010).
E.J. Greenspan, J.P. Madigan, L.A. Boardman and D.W. Rosenberg, Cancer Prev. Res., 4, 161 (2011).
H.N. Tinsley, B.D. Gary, J. Thaiparambil, N. Li, W. Lu, Y. Li, Y.Y. Maxuitenko, A.B. Keeton and G.A. Piazza, Cancer Prev. Res., 3, 1303 (2010).
M. Baumann and I.R. Baxendale, Beilstein J. Org. Chem., 9, 2265 (2013).
G.A. Piazza, A.B. Keeton, H.N. Tinsley, B.D. Gary, J.D. Whitt, B. Mathew, J. Thaiparambil, L. Coward, G. Gorman, Y. Li, B. Sani, J.V. Hobrath, Y.Y. Maxuitenko and R.C. Reynolds, Cancer Prev. Res., 2, 572 (2009).
M. Marjanovic, B. Zorc, L. Pejnovic, M. Zovko and M. Kralj, Chem. Biol. Drug Des., 69, 222 (2007).
T. Elsaman, O.A.A. Aldeeb, T. Aboul-Fadl and A. Al-Dhfyan, Der Pharma Chem., 8, 434 (2016).
R.K. Yeh, J. Chen, J.L. Williams, M. Baluch, T.R. Hundley, R.E. Rosenbaum, S. Kalala, F. Traganos, F. Benardini, P. Del Soldato, K. Kashfi and B. Rigas, Biochem. Pharmacol., 67, 2197 (2004).
T. Aboul-Fadl, S.S. Al-Hamad, K. Lee, N. Li, B.D. Gary, A.B. Keeton, G.A. Piazza and M.K. Abdel-Hamid, Med. Chem. Res., 23, 4177 (2014).
I. Delgado-Enciso, A.D. Soriano-Hernández, A. Rodriguez-Hernandez, H.R. Galvan-Salazar, D.A. Montes-Galindo, R. Martinez-Martinez, L.L. Valdez-Velazquez, R. Gonzalez-Alvarez, F. Espinoza-Gómez, O.A. Newton-Sanchez, A. Lara-Esqueda and J. Guzman-Esquivel, Int. Braz. J. Urol., 41, 1002 (2015).
T. Aboul-Fadl, T. Elsaman, O.A. Al-Deeb, H.A. Ghabbour, C.S. Chidan Kumar and H.-K. Fun, Asian J. Chem., 26, 5249 (2014).
A. Leo, Chem. Rev., 93, 1281 (1993).
M. Kralj, S. Kapitanovic, D. Kovacevic, J. Lukac, S. Spaventi and K. Pavelic, J. Cancer Res. Clin. Oncol., 127, 173 (2001).
P. Siraki, A. Chevaldina and T. O’Brien, Chem. Biol. Interact., 151, 177 (2005).