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Copyright (c) 2014 Azza A. Hussain1, Mohamed M. Abdulla2, Abd El-Galil E. Amr3, Mohamed A. Al-Omar3, Ahmed F.A. Shalaby1
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Anti-Inflammatory Activities of Some New Substituted Benzocarboxamide Pyrimidine Derivatives Using N-(4-Acetylphenyl)-5-chloro-2-methoxybenzamide as Starting Material
Corresponding Author(s) : Azza A. Hussain1
Asian Journal of Chemistry,
Vol. 26 No. 24 (2014)
Abstract
A series of substituted pyrimidine derivatives (2-6) were prepared from corresponding chalcones, which were prepared from N-(4-acetylphenyl)-5-chloro-2-methoxybenzamide as starting material. The structure assignments of the newly synthesized compounds are based on chemical and spectroscopic evidence. The pharmacological screening showed that many of these compounds have less toxicity and good anti-inflammatory activities.
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- A.M. Al-Mohizea, M.A. Al-Omar, M.M. Abdalla and A.E. Amr, Int. J. Biol. Macromol., 50, 171 (2012).
- A.E.-G.E. Amr, N.A. Abdel-Latif and M.M. Abdalla, Bioorg. Med. Chem., 14, 373 (2006).
- A.E. Amr, M.I. Hegab, A.A. Ibrahiem and M.M. Abdulla, Monatsh. Chem., 134, 1395 (2003).
- M. Abo-Ghalia and A. Amr, Amino Acids, 26, 283 (2004).
- A.M. Mohamed, A.E. Amr, M.A. Alsharari, H.R.M. Al-Qalawi, M.O. Germoush and M.A. Al-Omar, Am. J. Biochem. Biotech., 7, 43 (2011).
- A.E. Amr, A.M. Mohamed and A.A. Ibrahim, Z. Naturforsch., 58b, 861 (2003).
- A.E. Amr, O.I. Abd El-Salam, A.E.-H. Attia and I. Stibor, Coll. Czech. Chem. Commun., 64, 288 (1999).
- A. Attia, O.I. Abdel-Salam, I. Stibor, A.E. Amr and M. Budesinsky, Egypt. J. Chem., 43, 187 (2000).
- H.H. Fahmy and W. El-Eraky, Arch. Pharm. Res., 24, 171 (2001).
- M.H. Abou-Ghalia, A.E. Amr and M.M. Abdulla, Z. Naturforsch, 58b, 903 (2003).
- R. Nallangi, G. Samala, J.P. Sridevi, P. Yogeeswari and D. Sriram, Eur. J. Med. Chem., 76, 110 (2014).
- G. Samala, P.B. Devi, R. Nallangi, J.P. Sridevi, S. Saxena, P. Yogeeswari and D. Sriram, Bioorg. Med. Chem., 22, 1938 (2014).
- R. Baruchello, D. Simoni, P. Marchetti, R. Rondanin, S. Mangiola, C. Costantini, M. Meli, G. Giannini, L. Vesci, V. Carollo, T. Brunetti, G. Battistuzzi, M. Tolomeo and W. Cabri, Eur. J. Med. Chem., 76, 53 (2014).
- C. Congiu and V. Onnis, Bioorg. Med. Chem., 21, 6592 (2013).
- U. Reddy Chamakura, E. Sailaja, B. Dulla, A.M. Kalle, S. Bhavani, D. Rambabu, R. Kapavarapu, M.V.B. Rao and M. Pal, Bioorg. Med. Chem. Lett., 24, 1366 (2014).
- H. Liu, Y. Li, X.Y. Wang, B. Wang, H.Y. He, J.Y. Liu, M.L. Xiang, J. He, X.H. Wu and L. Yang, Bioorg. Med. Chem. Lett., 23, 2349 (2013).
- A.O. El-Nezhawy, A.R. Biuomy, F.S. Hassan, A.K. Ismaiel and H.A. Omar, Bioorg. Med. Chem., 21, 1661 (2013).
- H.H. Fahmy, N.M. Khalifa, E.S. Nossier, M.M. Abdalla and M.M. Ismai, Acta Pol. Pharm., 69, 411 (2012).
- X. Lu, H. Zhang, X. Li, G. Chen, Q.S. Li, Y. Luo, B.F. Ruan, X.W. Chen and H.L. Zhu, Bioorg. Med. Chem., 19, 6827 (2011).
- K.A. Abouzid, N.A. Khalil, E.M. Ahmed and S.A. Zaitone, Chem. Pharm. Bull. (Tokyo), 61, 222 (2013). (Tokyo).
- M.A. Hussein, R.M. Shaker, M.A. Ameen and M.F. Mohammed, Arch. Pharm. Res., 34, 1239 (2011).
- M.A. Metwally, M.A. Gouda, A.N. Harmal and A.M. Khalil, Eur. J. Med. Chem., 56, 254 (2012).
- S.C. Jain, J. Sinha, S. Bhagat, W. Errington and C.E. Olsen, Synth. Commun., 33, 563 (2003).
- M. Rajopadhye and F.D. Popp, J. Heterocycl. Chem., 24, 1637 (1987).
- J.S. Biradar and S.Y. Manjunath, Indian J. Chem., 43B, 389 (2004).
- V.V. Mulwad and A. Ali, J. Korean Chem. Soc., 52, 649 (2008).
- A. Dandia, R. Singh, S. Khaturia, C. Merienne, G. Morgant and A. Loupy, Bioorg. Med. Chem., 14, 2409 (2006).
- D. Kaminskyy, D. Khyluk, O. Vasylenko, L. Zaprutko and R. Lesyk, Sci. Pharm., 79, 763 (2011).
- M.M. Abdulla, A.E. Amr, A.A. Hussain, M.A. Al-Omar and A.F.A. Shalaby, Res. Chem. Intermed., 23, 2113 (2014).
- M.M. Abdulla, A.E. Amr, M.A. Al-Omar, A.A. Hussain and A.F.A. Shalaby, Med. Chem. Res., 23, 2113 (2014).
- M.M. Abdulla, A.E. Amr, M.A. Al-Omar, A.A. Hussain and A.F.A. Shalaby, Life Sci. J., 10, 286 (2013).
- C.A. Winter, E.A. Risley and G.W. Nuss, Proc. Soc. Exp. Biol. Med., 111, 544 (1962).
- F. Herrmann, A. Lindemann, J. Gauss and R. Mertelsmann, Eur. J. Immunol., 20, 2513 (1990).
References
A.M. Al-Mohizea, M.A. Al-Omar, M.M. Abdalla and A.E. Amr, Int. J. Biol. Macromol., 50, 171 (2012).
A.E.-G.E. Amr, N.A. Abdel-Latif and M.M. Abdalla, Bioorg. Med. Chem., 14, 373 (2006).
A.E. Amr, M.I. Hegab, A.A. Ibrahiem and M.M. Abdulla, Monatsh. Chem., 134, 1395 (2003).
M. Abo-Ghalia and A. Amr, Amino Acids, 26, 283 (2004).
A.M. Mohamed, A.E. Amr, M.A. Alsharari, H.R.M. Al-Qalawi, M.O. Germoush and M.A. Al-Omar, Am. J. Biochem. Biotech., 7, 43 (2011).
A.E. Amr, A.M. Mohamed and A.A. Ibrahim, Z. Naturforsch., 58b, 861 (2003).
A.E. Amr, O.I. Abd El-Salam, A.E.-H. Attia and I. Stibor, Coll. Czech. Chem. Commun., 64, 288 (1999).
A. Attia, O.I. Abdel-Salam, I. Stibor, A.E. Amr and M. Budesinsky, Egypt. J. Chem., 43, 187 (2000).
H.H. Fahmy and W. El-Eraky, Arch. Pharm. Res., 24, 171 (2001).
M.H. Abou-Ghalia, A.E. Amr and M.M. Abdulla, Z. Naturforsch, 58b, 903 (2003).
R. Nallangi, G. Samala, J.P. Sridevi, P. Yogeeswari and D. Sriram, Eur. J. Med. Chem., 76, 110 (2014).
G. Samala, P.B. Devi, R. Nallangi, J.P. Sridevi, S. Saxena, P. Yogeeswari and D. Sriram, Bioorg. Med. Chem., 22, 1938 (2014).
R. Baruchello, D. Simoni, P. Marchetti, R. Rondanin, S. Mangiola, C. Costantini, M. Meli, G. Giannini, L. Vesci, V. Carollo, T. Brunetti, G. Battistuzzi, M. Tolomeo and W. Cabri, Eur. J. Med. Chem., 76, 53 (2014).
C. Congiu and V. Onnis, Bioorg. Med. Chem., 21, 6592 (2013).
U. Reddy Chamakura, E. Sailaja, B. Dulla, A.M. Kalle, S. Bhavani, D. Rambabu, R. Kapavarapu, M.V.B. Rao and M. Pal, Bioorg. Med. Chem. Lett., 24, 1366 (2014).
H. Liu, Y. Li, X.Y. Wang, B. Wang, H.Y. He, J.Y. Liu, M.L. Xiang, J. He, X.H. Wu and L. Yang, Bioorg. Med. Chem. Lett., 23, 2349 (2013).
A.O. El-Nezhawy, A.R. Biuomy, F.S. Hassan, A.K. Ismaiel and H.A. Omar, Bioorg. Med. Chem., 21, 1661 (2013).
H.H. Fahmy, N.M. Khalifa, E.S. Nossier, M.M. Abdalla and M.M. Ismai, Acta Pol. Pharm., 69, 411 (2012).
X. Lu, H. Zhang, X. Li, G. Chen, Q.S. Li, Y. Luo, B.F. Ruan, X.W. Chen and H.L. Zhu, Bioorg. Med. Chem., 19, 6827 (2011).
K.A. Abouzid, N.A. Khalil, E.M. Ahmed and S.A. Zaitone, Chem. Pharm. Bull. (Tokyo), 61, 222 (2013). (Tokyo).
M.A. Hussein, R.M. Shaker, M.A. Ameen and M.F. Mohammed, Arch. Pharm. Res., 34, 1239 (2011).
M.A. Metwally, M.A. Gouda, A.N. Harmal and A.M. Khalil, Eur. J. Med. Chem., 56, 254 (2012).
S.C. Jain, J. Sinha, S. Bhagat, W. Errington and C.E. Olsen, Synth. Commun., 33, 563 (2003).
M. Rajopadhye and F.D. Popp, J. Heterocycl. Chem., 24, 1637 (1987).
J.S. Biradar and S.Y. Manjunath, Indian J. Chem., 43B, 389 (2004).
V.V. Mulwad and A. Ali, J. Korean Chem. Soc., 52, 649 (2008).
A. Dandia, R. Singh, S. Khaturia, C. Merienne, G. Morgant and A. Loupy, Bioorg. Med. Chem., 14, 2409 (2006).
D. Kaminskyy, D. Khyluk, O. Vasylenko, L. Zaprutko and R. Lesyk, Sci. Pharm., 79, 763 (2011).
M.M. Abdulla, A.E. Amr, A.A. Hussain, M.A. Al-Omar and A.F.A. Shalaby, Res. Chem. Intermed., 23, 2113 (2014).
M.M. Abdulla, A.E. Amr, M.A. Al-Omar, A.A. Hussain and A.F.A. Shalaby, Med. Chem. Res., 23, 2113 (2014).
M.M. Abdulla, A.E. Amr, M.A. Al-Omar, A.A. Hussain and A.F.A. Shalaby, Life Sci. J., 10, 286 (2013).
C.A. Winter, E.A. Risley and G.W. Nuss, Proc. Soc. Exp. Biol. Med., 111, 544 (1962).
F. Herrmann, A. Lindemann, J. Gauss and R. Mertelsmann, Eur. J. Immunol., 20, 2513 (1990).