Synthesis and Biological Screening of S-Substituted Derivatives of 5-{1-[(4-Chlorophenyl)sulfonyl]-3-piperidinyl}-1,3,4-oxadiazol-2-yl Sulfide

Khadija Nafeesa; Aziz-ur- Rehman; M. Athar Abbasi; Sabahat Z. Siddiqui; Shahid Rasool; Ghulam Hussain; Irshad Ahmed

doi:10.14233/ajchem.2015.17767

Issue

Vol. 27 No. 6 (2015): Vol 27 Issue 6

Issue Published : March 17, 2015

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

Synthesis and Biological Screening of S-Substituted Derivatives of 5-{1-[(4-Chlorophenyl)sulfonyl]-3-piperidinyl}-1,3,4-oxadiazol-2-yl Sulfide

https://doi.org/10.14233/ajchem.2015.17767

Khadija Nafeesa

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

Aziz-ur- Rehman

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

M. Athar Abbasi

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

Sabahat Z. Siddiqui

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

Shahid Rasool

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

Ghulam Hussain

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

Irshad Ahmed

Department of Pharmacy, Faculty of Pharmacy and Alternative Medicine, The Islamia University of Bahawalpur, Bahawalpur-63100, Pakistan

Corresponding Author(s) : Aziz-ur- Rehman

azizryk@yahoo.com, rehman@gcu.edu.pk

Asian Journal of Chemistry, Vol. 27 No. 6 (2015): Vol 27 Issue 6
Article Published : March 18, 2015

Abstract

In present research, a novel series of S-substituted derivatives of 5-[1-(4-chlorophenylsulfonyl)-3- piperidinyl]-1,3,4-oxadiazole-2-thiol (5a-f) was synthesized by multistep protocol starting from ethyl-3-piperidine carboxylate (a) geared up with 4-chlorobenzene sulfonyl chloride (b). The resulted ethyl-1-(4-chlorophenyl)sulfonyl piperidine-3-carboxylate (1) was subsequently converted into carbohydrazide (2) and then 2,5-disubstituted-1,3,4-oxadiazole by intermolecular cyclization. The compound 5-[1-(4-chlorophenylsulfonyl)-3-piperidinyl]-1,3,4-oxadiazole-2-thiol (3) was derivatized by different alkyl halides. All the synthesized compounds were characterized by IR, EIMS, ¹H NMR analysis and screened for antibacterial activity and enzyme inhibition potential against lipoxygenase enzyme.

Keywords

Sulfonamides Antibacterial activity Lipoxygenase activity Spectral analysis

Nafeesa, K., Rehman, A.- ur-., Athar Abbasi, M., Z. Siddiqui, S., Rasool, S., Hussain, G., & Ahmed, I. (2015). Synthesis and Biological Screening of S-Substituted Derivatives of 5-{1-[(4-Chlorophenyl)sulfonyl]-3-piperidinyl}-1,3,4-oxadiazol-2-yl Sulfide. Asian Journal of Chemistry, 27(6), 2105–2108. https://doi.org/10.14233/ajchem.2015.17767

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References

P.C. Sharma and S. Jain, Acta Pharm. Sciencia, 50, 35 (2008).
P.C. Sharma and S. Jain, Acta Pol. Pharm. Drug Res., 65, 551 (2008).
S. Wagle, A.A. Vasudeva and N.K. Suchetha, Indian J. Chem., 47B, 439 (2008).
B.S. Holla, K.N. Poojary, B. Kalluraya and P.V. Gowda, Indian J. Heterocycl. Chem., 5, 273 (1996).
S.S. Shafi and T.R. Radhakrishnan, Indian J. Heterocycl. Chem., 5, 133 (1995).
T.M. Tan, Y. Chen, K.H. Kong, J. Bai, Y. Li, S.G. Lim, H. Ang and Y. Lam, Antiviral Res., 71, 7 (2006); doi:10.1016/j.antiviral.2006.02.007.
K. Matsumoto, Y. Kawamura, Y. Yasuda, T. Tanimoto, K. Matsumoto, T. Yoshida and J. Shoji, J. Antibiot. (Tokyo), 42, 1465 (1989); doi:10.7164/antibiotics.42.1465.
F.A. Omar, N.M. Mahfouz and M.A. Rahman, Eur. J. Med. Chem., 31, 819 (1996); doi:10.1016/0223-5234(96)83976-6.
B.N. Goswami, J.C.S. Kataky and J.N. Baruah, J. Heterocycl. Chem., 21, 1225 (1984); doi:10.1002/jhet.5570210460.
M. Kaspady, V.K. Narayanaswamy, M. Raju and G.K. Rao, Lett. Drug Des. Discov., 6, 21 (2009); doi:10.2174/157018009787158481.
C.-R. Yang, Y. Zhang, M.R. Jacob, S.I. Khan, Y.-J. Zhang and X.-C. Li, Antimicrob. Agents Chemother., 50, 1710 (2006); doi:10.1128/AAC.50.5.1710-1714.2006.
H.C. Clapp, A. Banerjee and S.A. Rotenberg, Biochemistry, 24, 1826 (1985); doi:10.1021/bi00329a004.
S. Baylac and P. Racine, Int. J. Aromatherap., 13, 138 (2003); doi:10.1016/S0962-4562(03)00083-3.
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.

References

P.C. Sharma and S. Jain, Acta Pharm. Sciencia, 50, 35 (2008).

P.C. Sharma and S. Jain, Acta Pol. Pharm. Drug Res., 65, 551 (2008).

S. Wagle, A.A. Vasudeva and N.K. Suchetha, Indian J. Chem., 47B, 439 (2008).

B.S. Holla, K.N. Poojary, B. Kalluraya and P.V. Gowda, Indian J. Heterocycl. Chem., 5, 273 (1996).

S.S. Shafi and T.R. Radhakrishnan, Indian J. Heterocycl. Chem., 5, 133 (1995).

T.M. Tan, Y. Chen, K.H. Kong, J. Bai, Y. Li, S.G. Lim, H. Ang and Y. Lam, Antiviral Res., 71, 7 (2006); doi:10.1016/j.antiviral.2006.02.007.

K. Matsumoto, Y. Kawamura, Y. Yasuda, T. Tanimoto, K. Matsumoto, T. Yoshida and J. Shoji, J. Antibiot. (Tokyo), 42, 1465 (1989); doi:10.7164/antibiotics.42.1465.

F.A. Omar, N.M. Mahfouz and M.A. Rahman, Eur. J. Med. Chem., 31, 819 (1996); doi:10.1016/0223-5234(96)83976-6.

B.N. Goswami, J.C.S. Kataky and J.N. Baruah, J. Heterocycl. Chem., 21, 1225 (1984); doi:10.1002/jhet.5570210460.

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

C.-R. Yang, Y. Zhang, M.R. Jacob, S.I. Khan, Y.-J. Zhang and X.-C. Li, Antimicrob. Agents Chemother., 50, 1710 (2006); doi:10.1128/AAC.50.5.1710-1714.2006.

H.C. Clapp, A. Banerjee and S.A. Rotenberg, Biochemistry, 24, 1826 (1985); doi:10.1021/bi00329a004.

S. Baylac and P. Racine, Int. J. Aromatherap., 13, 138 (2003); doi:10.1016/S0962-4562(03)00083-3.

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.

Issue

Vol. 27 No. 6 (2015): Vol 27 Issue 6

Synthesis and Biological Screening of S-Substituted Derivatives of 5-{1-[(4-Chlorophenyl)sulfonyl]-3-piperidinyl}-1,3,4-oxadiazol-2-yl Sulfide

Corresponding Author(s) : Aziz-ur- Rehman

Abstract

Keywords

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