Abstract
Starting from the reaction of ethyl cyanoacetate with thiourea and the appropriate aldehydes, a series of new pyrimidine derivatives were prepared. Ten selected pyrimidine derivatives were subjected to a screening system for the investigation of their antitumor potency against liver (HEPG2) cell line. The antitumor activity results indicated that most of the selected pyrimidine derivatives showed moderate growth inhibition activity against the tested cell line, but with varying intensities in comparison to the known anticancer drugs: 5-fluorouracil and doxorubicin. Some of the synthesized compounds were also tested for their antimicrobial activity against bacteria as well as fungal isolates.
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References
P. Callery, P. Gannett, in Foye’s Principles of Medicinal Chemistry, ed. by D.A. Williams, T.L. Lemke (Lippincott Williams and Wilkins, Philadelphia, 2002), p. 934
R. Mishra, I. Tomar, IJPSR 2(4), 758–771 (2011)
O.N. Al Safarjalani, X.J. Zhou, R.H. Ras, J. Shi, R.F. Schinazi, F.N. Naguib, M.H. El Kouni, Cancer Chemother. Pharmacol. 55, 541–551 (2005)
M.S. Masoud, A.A. Ibrahim, E.A. Khalil, A. El-Marghany, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 67, 662–668 (2007)
A. Odani, H. Kozlowski, J. Swiatek-Kozlowska, J. Brasun, B.P. Operschall, H. Sigel, J. Inorg. Biochem. 101, 727–735 (2007)
C. Vetter, C. Wagner, G.N. Kaluđerović, R. Paschke, D. Steinborn, Inorg. Chim. Acta 362, 189–195 (2009)
M.N. Lipsett, J. Biol. Chem. 240, 3975 (1965)
W. Saenger, Principles of Nucleic Acid Structures (Springer, New York, 1984)
L. Lapinski, M.J. Nowak, R. Kolos, J.S. Kwiatkowski, J. Leszczynski, Spectrochim. Acta Part A 54, 685 (1998)
C. Heidelberelberger, K.C. Leibman and P.M., Bhargava, Cancer Res. 17, 39 (1957) C. A. 57, 16382 c (1957)
M.J. Straus, N. Mantel and A. Golden, Cancer Res. 33, 201(1960), C. A. 63, 8253 b (1960)
M.J. Straus, N. Mantel and A. Golden, Cancer Res. P. 126 (1962), C. A. 68, 32167 a (1962)
O.A. Fathalaa, W.A. Zaghary, H.H. Radwan, S.M. Awad, M.S. Mohamed, Arch. Pharm. Res. 25(3), 258 (2002)
P. Langen, Antimetabolites of Nucleic Acid Metabolism (Gordon and Breach, New York, 1975)
M. Friedland and D.W. Visser, Biochem. Biophys. Act. 51, 148 (1961), C. A. 70, 8032 a (1961)
G. Vansanten, F. Sorm, E.H. Siman, J. Biol. Chem. 237, 1271 (1965)
R.K. Zahn and U. Hagen, Mol. Pharmac. 1, 113 (1972), C. A. 90, 212 a (1972)
L. Sui, F. Wang, B.M. Li, Brain Res. 1096, 53 (2006)
O.A. Fathalla, H.H. Radwan, S.M. Awad, M.S. Mohamed, Indian J. Chem. 45B, 980–985 (2006)
A.A. Abu-Hashem, M.M. Youssef, H.A.R. Hussein, J. Chin. Chem. Soc. 58, 41–48 (2011)
S. Prachayasittikul, N. Sornsongkhram, R. Pingaew, S. Techatanachai, S. Ruchirawat, V. Prachayasittikul, Eur. J. Sci. Res. 36(2), 236–245 (2009)
A.Z. Abdel-Hamid, O.A. Fathalaa, J. Pharm. Sci. 34, 67 (1993)
O.A. Fathalaa, H.S.M. Gad, A.S. Maghraby, Arch. Pharm. Res. 23, 128 (2000)
O.A. Fathalla, I.F. Zeid, M.E. Haiba, W.S. El-Serwy, Egypt. Pharm. J. 4, 593–612 (2005)
O.A. Fathalla, I.F. Zeid, M.E. Haiba, A.M. Soliman, ShI Abd-Elmoez, W.S. El-Serwy, World J. Chem. 4(2), 127–132 (2009)
P. Skehan, R. Storeng, D. Scudiero, A. Anne Monks, J. McMahon, D. Vistica, J. Warren, H. Bokesch, S. Kenney, M. Boyd, J. Natl. Cancer Inst. 82, 1107 (1990)
M.H. Abo-Ghalia, A.M. Soliman, Acta Pol. Pharm. Drug Res. 57, 53 (2000)
K. Spencer, C.P. Price, Clin. Chim. Acta 95, 263 (1979)
A. Mays, Lab. Anim. Sci. 19, 838 (1969)
V. Joseph, Vet. Clin. North Am. Exot. Anim. Pract. 2, 689 (1999)
A.M. Soliman, L.M. Faddah, Egypt. J. Bilh. 16, 8 (1994)
A.H. Garde, A.M. Hansen, L.T. Skovgaard, J.M. Christensen, Clin. Chem. 47, 1877 (2001)
E.B. Rietz, G.G. Guilbault, Clin. Chem. 23, 286 (1977)
D.C. Turnell, Ann. Clin. Biochem. 22, 217 (1985)
N.L. Guilbaud, F. Kraus-Berthier, V. Meyer-Losic, C. Malivet, M. Chacun, F. Jan, S. Tillequin, M. Michel, B. Koch, Clin. Cancer Res. 7, 2573 (2001)
S. Bansod, M. Rai, World J. Med. Sci. 3(2), 81–88 (2008)
J.M. Andrews, J. Antimicrob. Chemother. 48, 5–16 (2001)
N.K. Sathish, V.V.S. Rajendra Prasad, N.M. Raghavendra, S.M. Shanta Kumar, Y.C. Mayur, Sci. Pharm. 77, 19 (2009)
S. Pautus, S.W. Yee, M. Jayne, M.P. Coogan, C. Simons, Bioorg. Med. Chem. 14, 3643 (2006)
I. Hayakawa, R. Shioya, T. Agatsuma, H. Furukawa, S. Naruto, Y. Sugano, Bioorg. Med. Chem. Lett. 14, 4383 (2004)
A. Espinosa, J. Marchal, A. Aránega, M. Gallo, S. Aiello, J. Campos, Farmaco 60, 91 (2005)
P. Kamalakannan, D. Venkappayya, J. Inorg. Biochem. 90, 22 (2002)
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Fathalla, O.A., Mohamed, N.A., El-Serwy, W.S. et al. Synthesis of some new pyrimidine derivatives and evaluation of their anticancer and antibacterial activities. Res Chem Intermed 39, 821–841 (2013). https://doi.org/10.1007/s11164-012-0597-7
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DOI: https://doi.org/10.1007/s11164-012-0597-7