İkhlass ABBAS, Sobhi GOMHA, Mahmoud ELAASSER, Mohammed BAUOMI

Synthesis and biological evaluation of new pyridines containing imidazole moiety as antimicrobial and anticancer agents

The synthesis of a novel series of pyridine and bipyridine derivatives is described via one-pot multicomponent reaction of 5-acetylimidazole, malonitrile (or ethylcyanoacetate or diethylmalonate), substituted benzaldehyde (or terephthaldehyde), and ammonium acetate in good yields. The structures of all the new compounds were elucidated on the basis of elemental analysis and spectral data. The antimicrobial activities of the synthesized compounds were screened and the results showed that most of such compounds exhibit considerable activities. Furthermore, some of the newly synthesized compounds were screened for their anticancer activity against human breast cell line (MCF-7) and liver carcinoma cell line (HEPG2) in comparison to doxorubicin. Most of the tested compounds exhibited promising activity.

Anahtar Kelimeler:

5-Acetylimidazole, cyanopyridone, bipyridine, multicomponent reactions, anticancer activity

Synthesis and biological evaluation of new pyridines containing imidazole moiety as antimicrobial and anticancer agents

Keywords:

5-Acetylimidazole, cyanopyridone, bipyridine, multicomponent reactions, anticancer activity,

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Zhang, J. Y. Nat. Rev. Drug Disc. 2002, 1, 101–102.
Buolamwini, J. K. Curr. Opin. Chem. Biol. 1999, 3, 500–509.
MacDonald, V. Can. Vet. J. 2009, 50, 665–668.
Borowski, E.; Bontemps-Gracz, M. M.; Piwkowska, A. Acta Biochim. Pol. 2005, 52, 609–627.
Cheney, I. W.; Yan, S.; Appleby, T.; Walker, H.; Vo, T.; Yao, N.; Hamatake, R.; Hong, Z.; Wu, J. Z. Bioorg. Med. Chem. Lett. 2007, 17, 1679–1683.
Wendt, M. D.; Sun, C.; Kunzer, A.; Sauer, D.; Sarris, K.; Hoff, E.; Yu, L. D.; Nettesheim, G.; Chen, J.; Jin, S.; et al. Bioorg. Med. Chem. Lett. 2007, 17, 3122–3129.
Aqui, N. A.; Vonderheide, R. H. Cancer Biol. Ther. 2008, 7, 1888–1889.
Ambrosini, G.; Adida, C.; Altieri, D. C. Nat. Med. 1997, 3, 917–921.
Gary, P.; Soh, J.-W.; Mao, Y.; Kim, M.-G.; Pamukcu, R.; Li, H.; Thompson, W. J.; Weinstein, I. B. Clin. Cancer Res. 2000, 6, 4136–4141.
Cheng, J.; Grande, J. P. Exp. Biol. Med. 2007, 232, 38–51.
Ranu, B. C.; Jana, R.; Sowmiah, S. J. Org. Chem. 2007, 72, 3152–3154.
Boger, D. L.; Nakahara, S. J. Org. Chem. 1991, 56, 880–884.
Ma, X.; Gang, D. R. Nat. Prod. Rep. 2004, 21, 752–772.
Ibrahim, H. S.; Eldehna, W. M.; Abdel-Aziz, H. A.; Elaasser, M. M.; Abdel-Aziz, M. M. Eur. J. Med. Chem. 2014, 85, 480–486.
Cohen, M. L. Nature 2000, 406, 762–767.
Bringmann, G.; Reichert, Y.; Kane, V. V. Tetrahedron 2004, 60, 3539–3574.
Son, J. K.; Zhao, L. X.; Basnet, A.; Thapa, P.; Karki, R.; Na, Y.; Jahng, Y.; Jeong, T. C.; Jeong, B. S.; Lee, C. S.; et al. Eur. J. Med. Chem. 2008, 43, 675–682.
Amr, A. G.; Abdulla, M. M. Bioorg. Med. Chem. 2006, 14, 4341–4352.
Zhao, L. X.; Sherchan, J.; Park, J. K.; Jahng, Y.; Jeong, B. S.; Jeong, T. C.; Lee, C. S.; Lee, E.-S. Arch. Pharm. Res. 2006, 29, 1091–1095.
Jeong, B.-S.; Choi, H.; Kwak, Y.-S.; Lee, E.-S. Bull. Korean Chem. Soc. 2011, 32, 3566–3570.
El-Sharkawy, K. A.; Ibrahim, R. A. Eur. Chem. Bull. 2013, 2, 530–537.
Weber, L. Curr. Med. Chem. 2002, 9, 2085–2093.
Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51–80.
Zhang, X. Y.; Li, Y. Z.; Fan, X. S. Chin. Chem. Lett. 2006, 17, 150–152.
Gomha, S. M.; Khalil, K. D. Molecules 2012, 17, 9335–9347.
Gomha, S. M.; Riyadh, S. M.; Abbas, I. M.; Bauomi, M. A. Heterocycles 2013, 87, 341–356.
Gomha, S. M.; Riyadh, S. M. Molecules 2011, 16, 8244–8256.
Gomha, S. M.; Abdel-Aziz. H. A. J. Serb. Chem. Soc. 2013, 78, 1119–1125.
Gomha, S. M.; Khalil, Kh. D.; El-Zanate, A. M.; Riyadh. S. M. Heterocycles 2013, 87, 1109–1120.
Gomha. S. M. Int. J. Pharm. Pharm. Sci. 2013, 5, 42–45.
Gomha, S. M.; Eldebss, T. M. A.; Abdulla, M. M.; Mayhoub, A. S. Eur. J. Med. Chem. 2014, 82, 472–479.
Gomha, S. M.; Abdel-Aziz, H. A. Bull. Korean Chem. Soc. 2012, 33, 2985–2990.
Gomha, S. M. Monatsh. Chem. 2009, 140, 213.
Gomha, S. M.; Shawali, A. S.; Abdelhamid, A. O. Turk. J. Chem. 2014, 38, 865– 879.
Dhawas, A. K.; Thakare, S. S.; Thakare, N. R. J. Chem. Pharm. Res. 2012, 4, 866–871.
Abadi, A. H.; Ibrahim, T. M.; Abouzid, K. M.; Lehmann, J.; Tinsley, H. N.; Gary, B. D.; Piazza, G. A. Bioorg. & Med. Chem. 2009, 17, 5974–5982.
Nehal, A.; Hamdy, A. M. G. Eur. J. Med. Chem. 2009, 44, 4547–4556.
El-Sayed, N. S.; Shirazi, A. N.; El-Meligy, M. G.; El-Ziaty, A. K.; Rowley, Sun, D. J.; Nagib, Z. A.; Parang, K. Tetrahedron Lett. 2014, 55, 1154–1158.
Smania, A.; Monache, F. D.; Smania, E. F. A.; Cuneo, R. S. Int. J. Med. Mushrooms 1999, 1, 325–330.
Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Nat. Cancer Inst. 1990, 82, 1107–1112.