Synthesis, Multiparametric Structure Assessment and Biological Evaluation of Some New 1,3,4-Oxadiazoles Containing Piperidine Nucleus

Javed Iqbal; Aziz-Ur-Rehman; Muhammad Athar Abbasi; Sabahat Zahra Siddiqui; Shahid Rasool; Muhammad Rehan; Syed Adnan Ali Shah

doi:10.14233/ajchem.2017.20564

Issue

Vol. 29 No. 9 (2017): Vol 29 Issue 9

Issue Published : July 15, 2017

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Multiparametric Structure Assessment and Biological Evaluation of Some New 1,3,4-Oxadiazoles Containing Piperidine Nucleus

https://doi.org/10.14233/ajchem.2017.20564

Javed Iqbal

Department of Chemistry, Government College University, Lahore-54000, Pakistan

Aziz-Ur-Rehman

Department of Chemistry, Government College University, Lahore-54000, Pakistan

Muhammad Athar Abbasi

Department of Chemistry, Government College University, Lahore-54000, Pakistan

Sabahat Zahra Siddiqui

Department of Chemistry, Government College University, Lahore-54000, Pakistan

Shahid Rasool

Department of Chemistry, Government College University, Lahore-54000, Pakistan

Muhammad Rehan

Department of Chemistry, Government College University, Lahore-54000, Pakistan

Syed Adnan Ali Shah

Faculty of Pharmacy and Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia

Corresponding Author(s) : Aziz-Ur-Rehman

azizryk@yahoo.com

Asian Journal of Chemistry, Vol. 29 No. 9 (2017): Vol 29 Issue 9
Article Published : July 15, 2017

Abstract

With an aim to introduce more biologically active compounds, S-substituted derivatives of 5-[1-(4-nitrophenylsulfonyl)piperidin-4-yl]-1,3,4-oxadiazole-2-thiol (3) were synthesized through four steps. In the first step, ethyl 1-(4-nitrophenylsulfonyl)piperidine-4-carboxylate (1) was synthesized by reacting 4-nitrobenzenesulfonyl chloride (a) and ethyl isonipacotate (b) in basic medium. In the second step, compound 1 and hydrazine monohydrate were converted to corresponding hydrazide (2). In third step, hydrazide (2), CS₂ and KOH were refluxed in the presence of MeOH to acquire 5-(1-(4-nitrophenylsulfonyl)piperidin-4-yl)-1,3,4-oxadiazole-2-thiol (3). In the last step, alkyl/aralkylhalides (4a-o) and 3 were made to react in an aprotic polar solvent to get the final compounds, 2-(substitutedthio)-5-[1-(4-nitrophenylsulfonyl)piperidin-4-yl]-1,3,4-oxadiazole (5a-o). The synthesized compounds were structurally confirmed by spectroscopic techniques including ¹H NMR, EIMS and IR. Finally the synthesized compounds were screened for antibacterial activity against five bacterial strains.

Keywords

Sulfonamide Ester 1,3,4-Oxadiazole Piperidine Antibacterial activity

Iqbal, J., Aziz-Ur-Rehman, ., Abbasi, M. A., Siddiqui, S. Z., Rasool, S., Rehan, M., & Ali Shah, S. A. (2017). Synthesis, Multiparametric Structure Assessment and Biological Evaluation of Some New 1,3,4-Oxadiazoles Containing Piperidine Nucleus. Asian Journal of Chemistry, 29(9), 1901–1906. https://doi.org/10.14233/ajchem.2017.20564

Download Citation

References

F. Macaev, G. Rusu, S. Pogrebnoi, A. Gudima, E. Stingaci, L. Vlad, N. Shvets, F. Kandemirli, A. Dimoglo and R. Reynolds, Bioorg. Med. Chem., 13, 4842 (2005); https://doi.org/10.1016/j.bmc.2005.05.011.
M. Al-Ghorbani, V. Vigneshwaran, V.L. Ranganatha, B.T. Prabhakar and S.A. Khanum, Bioorg. Chem., 60, 136 (2015); https://doi.org/10.1016/j.bioorg.2015.04.008.
D.D. Gaikwad, A.D. Chapolikar, C.G. Devkate, K.D. Warad, A.P. Tayade, R.P. Pawar and A.J. Domb, Eur. J. Med. Chem., 90, 707 (2015); https://doi.org/10.1016/j.ejmech.2014.11.029.
E. Palaska, G. Sahin, P. Kelicen, N.T. Durlu and G. Altinok, Farmaco, 57, 101 (2002); https://doi.org/10.1016/S0014-827X(01)01176-4.
M. Amir and K. Shikha, Eur. J. Med. Chem., 39, 535 (2004); https://doi.org/10.1016/j.ejmech.2004.02.008.
A. Zarghi, S.A. Tabatabai, A. Faizi, P. Ahadian, V. Navabi, A. Zanganeh and A. Shafiee, Bioorg. Med. Chem. Lett., 15, 1863 (2005); https://doi.org/10.1016/j.bmcl.2005.02.014.
J.J. Bhat, B.R. Shah, H.P. Shah, P.B. Trivedi, N.K. Undavia and N.C. Desai, Indian J. Chem., 33B, 189 (1994).
H.D. Gurupadaswamy, V. Girish, C.V. Kavitha, S.C. Raghavan and S.A. Khanum, Eur. J. Med. Chem., 63, 536 (2013); https://doi.org/10.1016/j.ejmech.2013.02.040.
H.D. Gurupadaswamy, P. Thirusangu, B.R. Vijay Avin, V. Vigneshwaran, M.V. Prashanth Kumar, T.S. Abhishek, V.L. Ranganatha, S.A. Khanum and B.T. Prabhakar, J. Biomed. Pharmacother., 68, 791 (2014); https://doi.org/10.1016/j.biopha.2014.07.004.
P.A. Clarke, A.V. Zaytzev and A.C. Whitwood, Tetrahedron Lett., 48, 5209 (2007);https://doi.org/10.1016/j.tetlet.2007.05.141.
K. Kamei, N. Maeda, R. Katsuragi-Ogino, M. Koyama, M. Nakajima, T. Tatsuoka, T. Ohno and T. Inoue, Bioorg. Med. Chem. Lett., 15, 2990 (2005); https://doi.org/10.1016/j.bmcl.2005.04.059.
M. Misra, S.K. Pandey, V.P. Pandey, J. Pandey, R. Tripathi and R.P. Tripathi, Bioorg. Med. Chem., 17, 625 (2009); https://doi.org/10.1016/j.bmc.2008.11.062.
Z.C. Wu, X. Wang, W. Wei and X. Chin, J. Synth. Chem., 22, 429 (2014).
D.H. Jiang and M. Huang, Chem. Reagents, 34, 797 (2012).
Aziz-ur-Rehman, H. Khalid, M.A.Abbasi, S.Gul, I. Ahmad and S. Arshad, J. Chem. Soc. Pak., 36, 131 (2014).
M. Kaspady, V.K. Narayanaswamy, M. Raju and G.K. Rao, Lett. Drug Des. Discov., 6, 21 (2009); https://doi.org/10.2174/157018009787158481.

References

F. Macaev, G. Rusu, S. Pogrebnoi, A. Gudima, E. Stingaci, L. Vlad, N. Shvets, F. Kandemirli, A. Dimoglo and R. Reynolds, Bioorg. Med. Chem., 13, 4842 (2005); https://doi.org/10.1016/j.bmc.2005.05.011.

M. Al-Ghorbani, V. Vigneshwaran, V.L. Ranganatha, B.T. Prabhakar and S.A. Khanum, Bioorg. Chem., 60, 136 (2015); https://doi.org/10.1016/j.bioorg.2015.04.008.

D.D. Gaikwad, A.D. Chapolikar, C.G. Devkate, K.D. Warad, A.P. Tayade, R.P. Pawar and A.J. Domb, Eur. J. Med. Chem., 90, 707 (2015); https://doi.org/10.1016/j.ejmech.2014.11.029.

E. Palaska, G. Sahin, P. Kelicen, N.T. Durlu and G. Altinok, Farmaco, 57, 101 (2002); https://doi.org/10.1016/S0014-827X(01)01176-4.

M. Amir and K. Shikha, Eur. J. Med. Chem., 39, 535 (2004); https://doi.org/10.1016/j.ejmech.2004.02.008.

A. Zarghi, S.A. Tabatabai, A. Faizi, P. Ahadian, V. Navabi, A. Zanganeh and A. Shafiee, Bioorg. Med. Chem. Lett., 15, 1863 (2005); https://doi.org/10.1016/j.bmcl.2005.02.014.

J.J. Bhat, B.R. Shah, H.P. Shah, P.B. Trivedi, N.K. Undavia and N.C. Desai, Indian J. Chem., 33B, 189 (1994).

H.D. Gurupadaswamy, V. Girish, C.V. Kavitha, S.C. Raghavan and S.A. Khanum, Eur. J. Med. Chem., 63, 536 (2013); https://doi.org/10.1016/j.ejmech.2013.02.040.

H.D. Gurupadaswamy, P. Thirusangu, B.R. Vijay Avin, V. Vigneshwaran, M.V. Prashanth Kumar, T.S. Abhishek, V.L. Ranganatha, S.A. Khanum and B.T. Prabhakar, J. Biomed. Pharmacother., 68, 791 (2014); https://doi.org/10.1016/j.biopha.2014.07.004.

P.A. Clarke, A.V. Zaytzev and A.C. Whitwood, Tetrahedron Lett., 48, 5209 (2007);https://doi.org/10.1016/j.tetlet.2007.05.141.

K. Kamei, N. Maeda, R. Katsuragi-Ogino, M. Koyama, M. Nakajima, T. Tatsuoka, T. Ohno and T. Inoue, Bioorg. Med. Chem. Lett., 15, 2990 (2005); https://doi.org/10.1016/j.bmcl.2005.04.059.

M. Misra, S.K. Pandey, V.P. Pandey, J. Pandey, R. Tripathi and R.P. Tripathi, Bioorg. Med. Chem., 17, 625 (2009); https://doi.org/10.1016/j.bmc.2008.11.062.

Z.C. Wu, X. Wang, W. Wei and X. Chin, J. Synth. Chem., 22, 429 (2014).

D.H. Jiang and M. Huang, Chem. Reagents, 34, 797 (2012).

Aziz-ur-Rehman, H. Khalid, M.A.Abbasi, S.Gul, I. Ahmad and S. Arshad, J. Chem. Soc. Pak., 36, 131 (2014).

M. Kaspady, V.K. Narayanaswamy, M. Raju and G.K. Rao, Lett. Drug Des. Discov., 6, 21 (2009); https://doi.org/10.2174/157018009787158481.

Issue

Vol. 29 No. 9 (2017): Vol 29 Issue 9

Synthesis, Multiparametric Structure Assessment and Biological Evaluation of Some New 1,3,4-Oxadiazoles Containing Piperidine Nucleus

Corresponding Author(s) : Aziz-Ur-Rehman

Abstract

Keywords

Full Article

Download Citation

References

Table Of Contents