Synthesis, Characterization and Biological Evaluation of New 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-1,2-dihydro-2-oxopyridine-3-carbonitrile

Mahmoud Al-Refai

doi:10.14233/ajchem.2015.17918

Issue

Vol. 27 No. 2 (2015): Vol 27 Issue 2

Issue Published : January 10, 2015

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

Synthesis, Characterization and Biological Evaluation of New 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-1,2-dihydro-2-oxopyridine-3-carbonitrile

https://doi.org/10.14233/ajchem.2015.17918

Mahmoud Al-Refai

Department of Chemistry, Faculty of Science, Al al-Bayt University, Al-Mafraq 25113, Jordan

Corresponding Author(s) : Mahmoud Al-Refai

mahmoud_alrefai@aabu.edu.jo

Asian Journal of Chemistry, Vol. 27 No. 2 (2015): Vol 27 Issue 2
Article Published : January 10, 2015

Abstract

Condensation of 3-acetyl-2,5-dichlorothiophene with different aldehydes in presence of ethyl cyanoacetate led to the formation of the new oxopyridine derivatives containing a thiophene moiety (3a-j) in high yields. All newly synthesized compounds were characterized by standard spectroscopic techniques. Antibacterial evaluation for all new compounds shows no activity against four different types of bacteria.

Keywords

Oxopyridine Ethyl cyanoacetate 3-Acetyl-2 5-dichlorothiophene 3-cyanopyridine- 2-one Condensation

Al-Refai, M. (2015). Synthesis, Characterization and Biological Evaluation of New 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-1,2-dihydro-2-oxopyridine-3-carbonitrile. Asian Journal of Chemistry, 27(2), 725–728. https://doi.org/10.14233/ajchem.2015.17918

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References

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References

A.H. Abadi, T.M. Ibrahim, K.M. Abouzid, J. Lehmann, H.N. Tinsley, B.D. Gary and G.A. Piazza, Bioorg. Med. Chem., 17, 5974 (2009); doi:10.1016/j.bmc.2009.06.063.

P. Fossa, G. Menozzi, P. Dorigo, M. Floreani and L. Mosti, Bioorg. Med. Chem., 11, 4749 (2003); doi:10.1016/S0968-0896(03)00528-5.

M. Kikura and J.H. Levy, Int. Anesthesiol. Clin., 33, 21 (1995); doi:10.1097/00004311-199500000-00002.

T. Kishi, K. Nakahashi, H. Ito, S. Taniguchi and M. Takaki, Clin. Exp. Pharmacol. Physiol., 28, 737 (2001); doi:10.1046/j.1440-1681.2001.03512.x.

S.R. Johns and L. Marion, Can. J. Chem., 44, 23 (1966); doi:10.1139/v66-004.

A. Piroyan and G. Melikyan, ARKIVOC, 234 (2006).

Y. Fujita, H. Oguri and H. Oikawa, Tetrahedron Lett., 46, 5885 (2005); doi:10.1016/j.tetlet.2005.06.115.

H.A. El-Sayed, A.H. Moustafa, A.Z. Haikal, R. Abu-El-Halawa and E.H. El Ashry, Eur. J. Med. Chem., 46, 2948 (2011); doi:10.1016/j.ejmech.2011.04.019.

M.T. Cocco, C. Congiu and V. Onnis, Eur. J. Med. Chem., 35, 545 (2000); doi:10.1016/S0223-5234(00)00149-5.

L.A. Hasvold, W. Wang, S.L. Gwaltney II, T.W. Rockway, L.T.J. Nelson, R.A. Mantei, S.A. Fakhoury, G.M. Sullivan, Q. Li, N.H. Lin, L. Wang, H. Zhang, J. Cohen, W.Z. Gu, K. Marsh, J. Bauch, S. Rosenberg and H.L. Sham, Bioorg. Med. Chem. Lett., 13, 4001 (2003); doi:10.1016/j.bmcl.2003.08.058.

N.S. El-Sayed, A.N. Shirazi, M.G. El-Meligy, A.K. El-Ziaty, D. Rowley, J. Sun, Z.A. Nagib and K. Parang, Tetrahedron Lett., 55, 1154 (2014); doi:10.1016/j.tetlet.2013.12.081.

R.L.T. Parreira, J.O. Abrahão Jr. and S.E. Galembeck, Tetrahedron, 57, 3243 (2001); doi:10.1016/S0040-4020(01)00193-4.

G. Semple, B.M. Andersson, V. Chhajlani, J. Georgsson, M.J. Johansson, Å. Rosenquist and L. Swanson, Bioorg. Med. Chem. Lett., 13, 1141 (2003); doi:10.1016/S0960-894X(03)00033-7.

V. Lucchesi, T. Parkkari, J.R. Savinainen, A.M. Malfitano, M. Allarà, S. Bertini, F. Castelli, S. Del Carlo, C. Laezza, A. Ligresti, G. Saccomanni, M. Bifulco, V. Di Marzo, M. Macchia and C. Manera, Eur. J. Med. Chem., 74, 524 (2014); doi:10.1016/j.ejmech.2013.10.070.

A. M. Abdel-Fattah, F. A. Attaby, M. A. A. Elneairy and M. N. M. Gouda, Curr. Bioact. Compd., 12, 176 (2012); doi:10.2174/157340712801784769.

E.R. Kotb, M.M. Anwar, H.A.S. Abbas and S.I. Abd El-Moez, Acta Pol. Pharm., 70, 667 (2013).

D.E. McClure, J.J. Baldwin, W.C. Randall, T.F. Lyon, K. Mensler, G.F. Lundell, A.W. Raab, D. Gross and E.A. Risley, J. Med. Chem., 26, 649 (1983); doi:10.1021/jm00359a006.

G.T. Wang, X. Wang, W. Wang, L.A. Hasvold, G. Sullivan, C.W. Hutchins, S. O'Conner, R. Gentiles, T. Sowin, J. Cohen, W.Z. Gu, H. Zhang, S.H. Rosenberg and H.L. Sham, Bioorg. Med. Chem. Lett., 15, 153 (2005); doi:10.1016/j.bmcl.2004.10.014.

G.B. Bachman and L.V. Heise, J. Am. Chem. Soc., 70, 2378 (1948); doi:10.1021/ja01187a019.

J.S. Parekh and S. Chanda, Afr. J. Biomed. Res., 10, 175 (2007); doi:10.4314/ajbr.v10i2.50624.

Issue

Vol. 27 No. 2 (2015): Vol 27 Issue 2

Synthesis, Characterization and Biological Evaluation of New 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-1,2-dihydro-2-oxopyridine-3-carbonitrile

Corresponding Author(s) : Mahmoud Al-Refai

Abstract

Keywords

Full Article

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