Synthesis, Characterization and Biological Evaluation of Some New Oxino bis-Pyrazole Derivatives

Abdul Ghafoor; Noreen Aslam; Mark C. Elliott; Naveed Sajid; Muhammad Nasrullah; Muhammad Ashraf; Qurat-ul-Ain; Misbahul Ain  Khan

doi:10.14233/ajchem.2016.19736

Issue

Vol. 28 No. 8 (2016): Vol 28 Issue 8

Issue Published : April 30, 2016

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

Synthesis, Characterization and Biological Evaluation of Some New Oxino bis-Pyrazole Derivatives

https://doi.org/10.14233/ajchem.2016.19736

Abdul Ghafoor

Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Noreen Aslam

Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Mark C. Elliott

School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK

Naveed Sajid

Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Muhammad Nasrullah

Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Muhammad Ashraf

Department of Biochemistry and Biotechnology, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Qurat-ul-Ain

Department of Biochemistry and Biotechnology, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Misbahul Ain Khan

Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Corresponding Author(s) : Abdul Ghafoor

agorg_ch@yahoo.com

Asian Journal of Chemistry, Vol. 28 No. 8 (2016): Vol 28 Issue 8
Article Published : April 30, 2016

Abstract

Novel oxino bis-pyrazoles were obtained by two step reactions of 3-methyl-1-phenyl pyrazoline-5-one, cyanoacetamide and aryl- or alkylaldehydes, in the presence of catalytic amounts of triethylamine and ethanol as a solvent. All the synthesized compounds were evaluated for their inhibitory activities against butyrylcholinesterase (BChE) and bovine a-chymotrypsin. Two compounds, 8 and 9 were found to be good inhibitors of enzyme BChE with IC₅₀ values of 52.74 ± 0.006 and 51.85 ± 0.005 μM, respectively.

Keywords

Bis-pyrazoles Multicomponent reactions Butyrylcholinesterase (BChE) Bovine a-Chymotrypsin

Ghafoor, A., Aslam, N., Elliott, M. C., Sajid, N., Nasrullah, M., Ashraf, M., … Khan, M. A. (2016). Synthesis, Characterization and Biological Evaluation of Some New Oxino bis-Pyrazole Derivatives. Asian Journal of Chemistry, 28(8), 1648–1652. https://doi.org/10.14233/ajchem.2016.19736

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References

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References

K.L. Kees, J.J. Fitzgerald, K.E. Steiner, J.F. Mattes, B. Mihan, T. Tosi, D. Mondoro and M.L. McCaleb, J. Med. Chem., 39, 3920 (1996); doi:10.1021/jm960444z.

V.J. Bauer, H.P. Dalalian, W.J. Fanshawe, S.R. Safir, E.C. Tocus and C.R. Boshart, J. Med. Chem., 11, 981 (1968); doi:10.1021/jm00311a015.

G.L. McNew and N.K. Sundholm, Phytopathology, 39, 721 (1949).

M.P. Lynch, J.R. Beck, E.V.P. Tao, J. Aikins, G.E. Babbitt, J.R. Rizzo and T.W. Waidrep, ACS Symposium Series, 443, 144 (1991).

G.A. Meier, I.R. Silverman, P.S. Ray, T.G. Cullen, S.F. Ali, F.L. Marek and C.A. Webster, ACS Symposium Series, 504, 313 (1992).

M.H. Elnagdi, M.R.H. Elmoghayar and G.E.H. Elgemeie, Adv. Heterocycl. Chem., 41, 319 (1987); doi:10.1016/S0065-2725(08)60164-6.

M.H. Elnagdi, M. Rifaat, H. Elmoghayer and K.U. Sadek, Adv. Heterocycl. Chem., 48, 223 (1990); doi:10.1016/S0065-2725(08)60340-2.

S.G. Kuo, L.J. Huang and H. Nakamura, J. Med. Chem., 27, 539 (1984); doi:10.1021/jm00370a020.

L.L. Adreani and E. Lapi, Boll. Chim. Pharm., 99, 583 (1960); Chem. Abstr., 55, 2668 (1961).

Y.L. Zhang, B.Z. Chen, K.Q. Zheng, M.L. Xu and X.H. Lei, Acta Pharm. Sinica, 17, 17 (1982); Chem. Abstr., 96, 135 (1982).

L. Bonsignore, G. Loy, D. Secci and A. Calignano, Eur. J. Med. Chem., 28, 517 (1993); doi:10.1016/0223-5234(93)90020-F.

E.C. Witte, P. Neubert and A. Roesch, Ger. Offen. DE 1986,3,427; Chem. Abstr., 104, 224 (1986).

J.L. Wang, D. Liu, Z.J. Zhang, S. Shan, X. Han, S.M. Srinivasula, C.M. Croce, E.S. Alnemri and Z. Huang, Proc. Natl. Acad. Sci. USA, 97, 7124 (2000); doi:10.1073/pnas.97.13.7124.

Y.A. Mohamed, M.A. Zahran, M.M. Ali, A.M. El-Agrody and U.H. El-Said, J. Chem. Res. (S), 322 (1995).

D. Armesto, W.M. Horspool, N. Martin, A. Ramos and C. Seoane, J. Org. Chem., 54, 3069 (1989); doi:10.1021/jo00274a021.

S. Hatakeyama, N. Ochi, H. Numata and S. Takano, J. Chem. Soc. Chem. Commun., 1202 (1988); doi:10.1039/C39880001202.

R. Gonzalez, N. Martin, C. Seoane and J. Soto, J. Chem. Soc., Perkin Trans. 1, 202 (1985).

K. Singh, J. Singh and H. Singh, Tetrahedron, 52, 14273 (1996);

doi:10.1016/0040-4020(96)00879-4.

S.A. El-Assiery, G.H. Sayed and A. Fouda, Acta Pharm. (Zagreb), 54, 143 (2004).

H.M.F. Madkour, M.R. Mahmoud, M.H. Nassar and M.M. Habashy, J. Chil. Chem. Soc., 47(4B), 937 (2000); doi:10.1002/jccs.200000128.

G.L. Ellman, K.D. Courtney, V. Andres Jr. and R.M. Featherstone, Biochem. Pharmacol., 7, 88 (1961); doi:10.1016/0006-2952(61)90145-9.

Issue

Vol. 28 No. 8 (2016): Vol 28 Issue 8

Synthesis, Characterization and Biological Evaluation of Some New Oxino bis-Pyrazole Derivatives

Corresponding Author(s) : Abdul Ghafoor

Abstract

Keywords

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