Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Urease Inhibiting Derivatives of 5-(3,4-Methylenedioxyphenyl)-1,3,4-Oxadiazol-2-thiol
Corresponding Author(s) : Aziz-ur Rehman
Asian Journal of Chemistry,
Vol. 26 No. 15 (2014): Vol 26 Issue 15
Abstract
In the present work, the urease inhibition activity of 1,3,4-oxadiazole bearing molecules was evaluated and were found to be potential inhibitors. 3,4-(Methylenedioxy)benzoic acid (1) was employed to synthesize 5-(3,4-methylenedioxyphenyl)-1,3,4-oxadiazol-2-thiol (4) via a series of steps. It was further stepped to yield S-substituted-5-(3,4-methylenedioxyphenyl)-1,3,4-oxadiazole derivatives (6a-h) on reaction with alkyl/aralkyl halides (5a-h) in DMF using LiH as an activator. All the synthesized compounds were well supported by IR, 1H NMR and EIMS spectral analysis. The enzyme inhibition activity against urease enzyme showed these molecules as potent inhibitors of this enzyme.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- B. Roy, A. Chakraborty, S.K. Ghosh and A. Basak, Bioorg. Med. Chem. Lett., 19, 7007 (2009); doi:10.1016/j.bmcl.2009.04.084.
- R.R. Somani and P.Y. Shirodkar, Der Pharm. Chem., 1, 130 (2009).
- N. Jaiswal, A.K. Singh, D. Singh and T. Ahmad, Int. Res. J. Pharm., 3, 83 (2012).
- Aziz-ur-Rehman A. Fatima, N. Abbas, M.A. Abbasi, K.M. Khan, M. Ashraf, I. Ahmad and S.A. Ejaz, Pak. J. Pharm. Sci., 26, 345 (2013).
- Aziz-ur-Rehman, A. Fatima, M.A. Abbasi, S. Rasool, A. Malik, M. Ashraf, I. Ahmad and S.A. Ejaz, J. Saudi Chem. Soc., doi:10.1016/j.jscs.2013.02.006.
- H. Khalid, Aziz-ur-Rehman, M.A. Abbasi, A. Malik, S. Rasool, K. Nafeesa, I. Ahmad and S. Afzal, J. Saudi Chem. Soc., doi:10.1016/j.jscs.2013.05.001.
- L. Ingrassia, F. Lefranc, V. Mathieu, F. Darro and R. Kiss, Translational Oncol., 1, 1 (2008); doi:10.1593/tlo.08100.
- B. Bar-Oz, T. Einarson, A. Einarson, R. Boskovic, L. O'Brien, H. Malm, A. Berard and G. Koren, Clin. Ther., 29, 918 (2007); doi:10.1016/j.clinthera.2007.05.003.
- H.L.T. Mobley, M.D. Island and R.P. Hausinger, Microbiol. Rev., 59, 451 (1995).
- M.A. Lodhi, M.A. Abbasi, M.I. Choudhary and V.U. Ahmad, Nat. Prod. Res., 21, 721 (2007); doi:10.1080/14786410600906913.
- M.A. Lodhi, J. Hussain, M.A. Abbasi, A.R. Jassbi, M.I. Choudhary and V.U. Ahmad, J. Enzyme Inhib. Med. Chem., 21, 531 (2006); doi:10.1080/14756360600586072.
- Aziz-ur-Rehman S.Z. Siddiqui, N. Abbas, M.A. Abbasi, K.M. Khan, M. Shahid, Y. Mahmood, N.M. Akhtar and N.H. Lajis, Int. J. Pharm. Pharm. Sci., 4, 676 (2012).
- Aziz-ur-Rehman K. Nafeesa, M.A. Abbasi, H. Khalid, K.M. Khan, M. Ashraf, I. Ahmad and S.A. Ejaz, Asian J. Pharm. Heath Sci., 2, 370 (2012).
- H.L. Mobley, M.J. Cortesia, L.E. Rosenthal and B.D. Jones, J. Clin. Microbiol., 26, 831 (1988).
References
B. Roy, A. Chakraborty, S.K. Ghosh and A. Basak, Bioorg. Med. Chem. Lett., 19, 7007 (2009); doi:10.1016/j.bmcl.2009.04.084.
R.R. Somani and P.Y. Shirodkar, Der Pharm. Chem., 1, 130 (2009).
N. Jaiswal, A.K. Singh, D. Singh and T. Ahmad, Int. Res. J. Pharm., 3, 83 (2012).
Aziz-ur-Rehman A. Fatima, N. Abbas, M.A. Abbasi, K.M. Khan, M. Ashraf, I. Ahmad and S.A. Ejaz, Pak. J. Pharm. Sci., 26, 345 (2013).
Aziz-ur-Rehman, A. Fatima, M.A. Abbasi, S. Rasool, A. Malik, M. Ashraf, I. Ahmad and S.A. Ejaz, J. Saudi Chem. Soc., doi:10.1016/j.jscs.2013.02.006.
H. Khalid, Aziz-ur-Rehman, M.A. Abbasi, A. Malik, S. Rasool, K. Nafeesa, I. Ahmad and S. Afzal, J. Saudi Chem. Soc., doi:10.1016/j.jscs.2013.05.001.
L. Ingrassia, F. Lefranc, V. Mathieu, F. Darro and R. Kiss, Translational Oncol., 1, 1 (2008); doi:10.1593/tlo.08100.
B. Bar-Oz, T. Einarson, A. Einarson, R. Boskovic, L. O'Brien, H. Malm, A. Berard and G. Koren, Clin. Ther., 29, 918 (2007); doi:10.1016/j.clinthera.2007.05.003.
H.L.T. Mobley, M.D. Island and R.P. Hausinger, Microbiol. Rev., 59, 451 (1995).
M.A. Lodhi, M.A. Abbasi, M.I. Choudhary and V.U. Ahmad, Nat. Prod. Res., 21, 721 (2007); doi:10.1080/14786410600906913.
M.A. Lodhi, J. Hussain, M.A. Abbasi, A.R. Jassbi, M.I. Choudhary and V.U. Ahmad, J. Enzyme Inhib. Med. Chem., 21, 531 (2006); doi:10.1080/14756360600586072.
Aziz-ur-Rehman S.Z. Siddiqui, N. Abbas, M.A. Abbasi, K.M. Khan, M. Shahid, Y. Mahmood, N.M. Akhtar and N.H. Lajis, Int. J. Pharm. Pharm. Sci., 4, 676 (2012).
Aziz-ur-Rehman K. Nafeesa, M.A. Abbasi, H. Khalid, K.M. Khan, M. Ashraf, I. Ahmad and S.A. Ejaz, Asian J. Pharm. Heath Sci., 2, 370 (2012).
H.L. Mobley, M.J. Cortesia, L.E. Rosenthal and B.D. Jones, J. Clin. Microbiol., 26, 831 (1988).