Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Spectral and Enzyme Inhibition Studies on N-Aralkyl/Aryl Sulfonated Derivatives of Commercially Available Paroxetine
Corresponding Author(s) : Aziz-ur Rehman
Asian Journal of Chemistry,
Vol. 26 No. 1 (2014): Vol 26 Issue 1
Abstract
In the current work, a facile and environmentally benign series of N-aralkyl/aryl sulfonyl paroxetine 3a-n was synthesized and screened against lipoxygenase enzyme. These were geared up by the coupling of paroxetine (1) with different aralkyl/aryl sulfonyl chlorides, 2a-n, under dynamic pH control in aqueous basic media to form various N-substituted paroxetine (3a-l). The synthesized compounds were characterized by spectral data like IR, 1H NMR, 13C NMR and EI-MS. The bioactivity of all the synthesized compounds was evaluated against lipoxygenase (LOX) enzyme. Only six synthesized compounds showed moderate activity but all others remained inactive against lipoxygenase enzyme as it was evident from their IC50 values, relative to the standard used.
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- S.P. Runyon, J.P. Burgess, P. Abraham, K.I. Keverline-Frantz, J. Flippen-Anderson, J. Deschamps, A.H. Lewin, H.A. Navarro, J.W. Boja, M.J. Kuhar and F.I. Carrol, Bioorg. Med. Chem., 13, 2439 (2005); doi:10.1016/j.bmc.2005.01.046.
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- J. Cossy, O. Mirguet, D. Gomez Pardo and J.-R. Desmurs, Tetrahedron Lett., 42, 5705 (2001); doi:10.1016/S0040-4039(01)01096-6.
- A. Alsughayer, A.A. Elassar, S. Mustafa and F. Sagheer, J. Biomater. Nanobiotechnol., 2, 143 (2011); doi:10.4236/jbnb.2011.22018.
- J.M. Baskin and Z. Wang, Tetrahedron Lett., 43, 8479 (2002); doi:10.1016/S0040-4039(02)02073-7.
- S. Kumar, M.S. Niranjan, K.C. Chaluvaraju, C.M. Jamakhandi and D. Kadadevar, J. Curr. Pharm. Res., 1, 39 (2010).
- N. Ozbek, H. Katircioglu, N. Karacan and T. Baykal, Bioorg. Med. Chem., 15, 5105 (2007); doi:10.1016/j.bmc.2007.05.037.
- F. Shi, M.K. Tse, S. Zhou, M.-M. Pohl, J. Radnik, S. Hübner, K. Jähnisch, A. Brückner and M. Beller, J. Am. Chem. Soc., 131, 1775 (2009); doi:10.1021/ja807681v.
- M.A. Abbasi, V.U. Ahmad, M. Zubair, M.A. Rashid, U. Farooq, S.A. Nawaz, M.A. Lodhi, T. Makhmoor, M.I. Choudhary and Atta-ur-Rahman, Proc. Pak. Acad. Sci., 42, 121(2005).
- G.A. Alitonou, F. Avlessi, D.K. Sohounhloue, H. Agnaniet, J.M. Bessiere and C. Menut, Int. J. Aromather, 16, 37 (2006); doi:10.1016/j.ijat.2006.01.001.
- R.S. Byrum, J.L. Goulet, R.J. Griffiths and B.H. Koller, J. Exp. Med., 185, 1065 (1997); doi:10.1084/jem.185.6.1065.
- H. Khalid, Aziz-ur-Rehman, M.A. Abbasi and K.M. Khan, Int. J. Pharm. Pharm. Sci., 4, 443 (2012).
- Aziz-ur-Rehman, S. Afroz, M.A. Abbasi, W. Tanveer, K.M. Khan, M. Asraf, I. Afzal, and N. Ambreen, Pak. J. Pharm. Sci., 25, 809 (2012).
- S. Baylac and P. Racine, Int. J. Aromatherap., 13, 138 (2003); doi:10.1016/S0962-4562(03)00083-3.
- P. Jakubec, D.M. Cockfield, M. Helliwell, J. Raftery and D.J. Dixon, Beilstein J. Org. Chem., 8, 567 (2012); doi:10.3762/bjoc.8.64.
References
S.P. Runyon, J.P. Burgess, P. Abraham, K.I. Keverline-Frantz, J. Flippen-Anderson, J. Deschamps, A.H. Lewin, H.A. Navarro, J.W. Boja, M.J. Kuhar and F.I. Carrol, Bioorg. Med. Chem., 13, 2439 (2005); doi:10.1016/j.bmc.2005.01.046.
K. Sugi, N. Itaya, T. Katsura, M. Igi, S. Yamazaki, T. Ishibashi, T. Yamaoka, Y. Kawada, Y. Tagami, M. Otsuki and T. Ohshima, Chem. Pharm. Bull. (Tokyo), 48, 529 (2000); doi:10.1248/cpb.48.529.
J. Cossy, O. Mirguet, D. Gomez Pardo and J.-R. Desmurs, Tetrahedron Lett., 42, 5705 (2001); doi:10.1016/S0040-4039(01)01096-6.
A. Alsughayer, A.A. Elassar, S. Mustafa and F. Sagheer, J. Biomater. Nanobiotechnol., 2, 143 (2011); doi:10.4236/jbnb.2011.22018.
J.M. Baskin and Z. Wang, Tetrahedron Lett., 43, 8479 (2002); doi:10.1016/S0040-4039(02)02073-7.
S. Kumar, M.S. Niranjan, K.C. Chaluvaraju, C.M. Jamakhandi and D. Kadadevar, J. Curr. Pharm. Res., 1, 39 (2010).
N. Ozbek, H. Katircioglu, N. Karacan and T. Baykal, Bioorg. Med. Chem., 15, 5105 (2007); doi:10.1016/j.bmc.2007.05.037.
F. Shi, M.K. Tse, S. Zhou, M.-M. Pohl, J. Radnik, S. Hübner, K. Jähnisch, A. Brückner and M. Beller, J. Am. Chem. Soc., 131, 1775 (2009); doi:10.1021/ja807681v.
M.A. Abbasi, V.U. Ahmad, M. Zubair, M.A. Rashid, U. Farooq, S.A. Nawaz, M.A. Lodhi, T. Makhmoor, M.I. Choudhary and Atta-ur-Rahman, Proc. Pak. Acad. Sci., 42, 121(2005).
G.A. Alitonou, F. Avlessi, D.K. Sohounhloue, H. Agnaniet, J.M. Bessiere and C. Menut, Int. J. Aromather, 16, 37 (2006); doi:10.1016/j.ijat.2006.01.001.
R.S. Byrum, J.L. Goulet, R.J. Griffiths and B.H. Koller, J. Exp. Med., 185, 1065 (1997); doi:10.1084/jem.185.6.1065.
H. Khalid, Aziz-ur-Rehman, M.A. Abbasi and K.M. Khan, Int. J. Pharm. Pharm. Sci., 4, 443 (2012).
Aziz-ur-Rehman, S. Afroz, M.A. Abbasi, W. Tanveer, K.M. Khan, M. Asraf, I. Afzal, and N. Ambreen, Pak. J. Pharm. Sci., 25, 809 (2012).
S. Baylac and P. Racine, Int. J. Aromatherap., 13, 138 (2003); doi:10.1016/S0962-4562(03)00083-3.
P. Jakubec, D.M. Cockfield, M. Helliwell, J. Raftery and D.J. Dixon, Beilstein J. Org. Chem., 8, 567 (2012); doi:10.3762/bjoc.8.64.